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  • Beautiful Spacious Escape On The Chain O'Lakes
    From $401 per night (USD)

    VRBO

    Beautiful Spacious Escape On The Chain O'Lakes

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    Escape to the beauty of the Chain O'Lakes. Spend the weekend or full weeks vacation on the shores of Lake Pistakee in ou ...

    From $401 per night (USD)

    VRBO

    Details
  • Lakefront 5BR · Dock, Kayaks, Hot Tub & Beach
    From $656 per night (USD)

    Expedia

    Lakefront 5BR · Dock, Kayaks, Hot Tub & Beach

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Experience lakeside luxury at Sunset Shores, your 5-bedroom retreat on the beautiful Lake of Egypt. Designed to host up ...

    From $656 per night (USD)

    Expedia

    Details
  • *Stone Fire Pit*Hot Tub* Pool Table & Arcade Game*
    From $615 per night (USD)

    VRBO

    *Stone Fire Pit*Hot Tub* Pool Table & Arcade Game*

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Oakmont Lodge is 1 mile from the GTA Owners Club and a 7 mile drive to downtown Galena. This home is dog-friendly, with ...

    From $615 per night (USD)

    VRBO

    Details
  • Miller lakehouse.  Pontoon available to rent
    From $336 per night (USD)

    Expedia

    Miller lakehouse. Pontoon available to rent

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Great patio view overlooking the lake. Easy walk to the boat dock and sun deck. 3 bedrooms 3 bathrooms. Master bathro ...

    From $336 per night (USD)

    Expedia

    Details
  • Family Home on Lake Sara
    From $387 per night (USD)

    VRBO

    Family Home on Lake Sara

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    The Bunkhouse is a fantastic place for families and friends to reconnect and make lasting memories. With walk-in lake ac ...

    From $387 per night (USD)

    VRBO

    Details
  • Cozy Cabin In Roselle
    From $231 per night (USD)

    Expedia

    Cozy Cabin In Roselle

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    If you’re looking for the ideal cozy place to feel at home that is affordable and close to Elgin O'Hare there’s nothing ...

    From $231 per night (USD)

    Expedia

    Details
  • House and party Barn on 300 acres, hot tub, 10 miles views, Private golf, trails
    From $819 per night (USD)

    VRBO

    House and party Barn on 300 acres, hot tub, 10 miles views, Private golf, trails

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    13

    This listing Includes both a main House and an entertainment building..... SO TWO BUILDINGS.....40 feet apart. The house ...

    From $819 per night (USD)

    VRBO

    Details
  • 2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
    From $318 per night (USD)

    Expedia

    2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Amazing location, immaculately clean and updated 2BR/1BA unit is 4 blocks to Fox River Bike Trail, 1 mile to popular dow ...

    From $318 per night (USD)

    Expedia

    Details
  • A perfect weekend gateway!
    From $496 per night (USD)

    VRBO

    A perfect weekend gateway!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This spacious 2400+ sq/ft home overlooks downtown Grafton and the confluence of the Mississippi and Illinois rivers. It ...

    From $496 per night (USD)

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    Details
  • Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.
    From $540 per night (USD)

    Expedia

    Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Located at 19 Farmstead Lane. This is a three level townhome with 4 bedrooms, 2 with queen beds, 1 with 2 double beds an ...

    From $540 per night (USD)

    Expedia

    Details
  • Lakeside Shady Rest Home Away from Home blocks from Rend Lake and I57/I64
    From $225 per night (USD)

    VRBO

    Lakeside Shady Rest Home Away from Home blocks from Rend Lake and I57/I64

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Take it easy at this unique and tranquil getaway 1/2 mile off Interstate 57 and 9 miles from Interstate 64. Convenient f ...

    From $225 per night (USD)

    VRBO

    Details
  • Modern 4 Bedroom 2 Bath Sleeps 10 Newly Renovated Whole House Rental
    From $602 per night (USD)

    Expedia

    Modern 4 Bedroom 2 Bath Sleeps 10 Newly Renovated Whole House Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Brand new to the rental market...fully remodeled, modern, comfortable and super cute river home! This house was recently ...

    From $602 per night (USD)

    Expedia

    Details
  • Golf View, Walking Trails, Dog Friendly & Access to Indoor Pool
    From $173 per night (USD)

    VRBO

    Golf View, Walking Trails, Dog Friendly & Access to Indoor Pool

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Green View Getaway is just minutes to our GTA Owners Club or a brisk walk to the pools, tennis courts, gym, etc. or a 7- ...

    From $173 per night (USD)

    VRBO

    Details
  • Top floor of Historic Oak Park Home /2 Car Garage
    From $399 per night (USD)

    Expedia

    Top floor of Historic Oak Park Home /2 Car Garage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Fran ...

    From $399 per night (USD)

    Expedia

    Details
  • Spacious , next to pools, shuffleboard, screened porch
    From $492 per night (USD)

    VRBO

    Spacious , next to pools, shuffleboard, screened porch

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Older home with Living Room, Dining Room, Kitchen, Lower Level Family Room, Deck and Gas Grill, Wood Fireplace, 2 King B ...

    From $492 per night (USD)

    VRBO

    Details
  • GORGEOUS LARGE HOME WITH HOT TUB!Golden Tee & Foosball Table!
    From $1559 per night (USD)

    Expedia

    GORGEOUS LARGE HOME WITH HOT TUB!Golden Tee & Foosball Table!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    4500 Square foot home on over 5 acres. with a view of the 5th hole of "The General" golf course. This home features a l ...

    From $1559 per night (USD)

    Expedia

    Details
  • Sunset Cottage on Lake Pistakee
    From $240 per night (USD)

    VRBO

    Sunset Cottage on Lake Pistakee

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Escape to the beauty of the Chain O'Lakes to spend the weekend or a lengthy stay on the shores of Lake Pistakee. Enjoy ...

    From $240 per night (USD)

    VRBO

    Details
  • Simply Stunning Views! 2 Fireplaces/Pool Table/Fire Pit and Owners' Club Access!
    From $855 per night (USD)

    Expedia

    Simply Stunning Views! 2 Fireplaces/Pool Table/Fire Pit and Owners' Club Access!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    <p><strong>The Galena Log Home, Galena IL</strong></p> <p><strong>Entire Home Vacation Rental, 5 Bed, 4 Bath, 12 Person ...

    From $855 per night (USD)

    Expedia

    Details
  • Campbell Street Cottage
    From $543 per night (USD)

    VRBO

    Campbell Street Cottage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Charming Historic Cottage in Downtown Geneva, IL Discover the blend of historic charm and modern comfort in this beautif ...

    From $543 per night (USD)

    VRBO

    Details
  • Blue Suede Suites North
    From $254 per night (USD)

    Expedia

    Blue Suede Suites North

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wonderful newer constructed 2 bedroom condo built on the banks of the beautiful Mississippi River. Enjoy the spectacula ...

    From $254 per night (USD)

    Expedia

    Details
  • Stylish Luxe King bed w/Free Parkng near DT Oak Pk
    From $289 per night (USD)

    VRBO

    Stylish Luxe King bed w/Free Parkng near DT Oak Pk

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This beautifully designed, fully equipped apartment offers comfort, space, and convenience in one of Oak Park’s most des ...

    From $289 per night (USD)

    VRBO

    Details
  • Welcome to your Galena Get Away!!!
    From $276 per night (USD)

    Expedia

    Welcome to your Galena Get Away!!!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to the Galena Get Away! Get away from it all in this updated townhouse. This 3 bedroom, 3 bath town home is ce ...

    From $276 per night (USD)

    Expedia

    Details
  • Windjammer, Lakefront Home-Away-From-Home!!!
    From $1495 per night (USD)

    VRBO

    Windjammer, Lakefront Home-Away-From-Home!!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    16

    Luxurious resort-style property has its own shoreline beach and truly unbeatable scenic views! An open-concept floor pl ...

    From $1495 per night (USD)

    VRBO

    Details
  • Modern Home in Trendy Neighborhood 40 from Downtown Chicago
    From $375 per night (USD)

    Expedia

    Modern Home in Trendy Neighborhood 40 from Downtown Chicago

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This Newly Remodeled Modern Smart Home is great for family vacations, stay cations and traveling professionals. 4 Bedroo ...

    From $375 per night (USD)

    Expedia

    Details
  • Worldmark Galena - 1BD
    From $137 per night (USD)

    VRBO

    Worldmark Galena - 1BD

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    WorldMark Galena is situated near Eagle Ridge Resort`s General, the most challenging of the four world-class Galena terr ...

    From $137 per night (USD)

    VRBO

    Details
  • Enjoy Spectacular Sunset Views ☀️ On True Lakefront
    From $214 per night (USD)

    Expedia

    Enjoy Spectacular Sunset Views ☀️ On True Lakefront

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Amenities include a brand new 600 square foot deck with unobstructed views of the Fox Chain O' Lakes for the grill-maste ...

    From $214 per night (USD)

    Expedia

    Details
  • Prairieview Cottage Retreat - Hot Tub Sunsets
    From $389 per night (USD)

    VRBO

    Prairieview Cottage Retreat - Hot Tub Sunsets

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    REST, RELAX, RETREAT... Escape to tranquility at this picturesque, pet-friendly cottage, nestled in the serene countrysi ...

    From $389 per night (USD)

    VRBO

    Details
  • Experience Belleville in a 2 BR cozy home with a STL Cardinals theme.
    From $251 per night (USD)

    Expedia

    Experience Belleville in a 2 BR cozy home with a STL Cardinals theme.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy this peaceful home with a tranquil view of a private pond located right outside the back door. It includes a STL C ...

    From $251 per night (USD)

    Expedia

    Details
  • Unity Lodge Suite 5
    From $129 per night (USD)

    VRBO

    Unity Lodge Suite 5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    The private room has two full-size beds, private bath, private entrance, a desk, and a TV. It is part of a 12-room lodge ...

    From $129 per night (USD)

    VRBO

    Details
  • Unity Lodge Suite 7
    From $136 per night (USD)

    Expedia

    Unity Lodge Suite 7

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The private room has two full-size beds, private bath, private entrance, a desk, and a TV. It is part of a 12-room lodge ...

    From $136 per night (USD)

    Expedia

    Details
  • Unity Lodge Suite 6
    From $136 per night (USD)

    VRBO

    Unity Lodge Suite 6

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The private room has two full-size beds, private bath, private entrance, a desk, and a TV. It is part of a 12-room lodge ...

    From $136 per night (USD)

    VRBO

    Details
  • Unity Lodge Suite 10
    From $112 per night (USD)

    VRBO

    Unity Lodge Suite 10

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The private room has four single beds, private bath, private entrance, a desk, and a TV. It is part of a 12-room lodge o ...

    From $112 per night (USD)

    VRBO

    Details
  • Rocky Ridge Getaway Joins Shawnee Forest
    From $172 per night (USD)

    VRBO

    Rocky Ridge Getaway Joins Shawnee Forest

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Just steps away from the captivating beauty of The Shawnee National Forest, Rocky Ridge offers unmatched tranquility and ...

    From $172 per night (USD)

    VRBO

    Details
  • Unity Lodge Suite 2
    From $136 per night (USD)

    Expedia

    Unity Lodge Suite 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The private room has two full-size beds, private bath, private entrance, a desk, and a TV. It is part of a 12-room lodge ...

    From $136 per night (USD)

    Expedia

    Details
  • 2 Bedroom, 2 bath townhouse in The Galena Territory.
    From $252 per night (USD)

    VRBO

    2 Bedroom, 2 bath townhouse in The Galena Territory.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    END UNIT with a wooded view! This nicely decorated 2-bed, 2-bath end unit townhome is located on the South Golf Course, ...

    From $252 per night (USD)

    VRBO

    Details
  • Chicago's Hidden Treasure \Evanston, IL\ Urban Luxury with comfort
    From $421 per night (USD)

    Expedia

    Chicago's Hidden Treasure \"Evanston, IL\" Urban Luxury with comfort

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Urban Luxe experience, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Univ ...

    From $421 per night (USD)

    Expedia

    Details
  • Close to Galena, close to perfect. Premier get away.  Three beautiful suites.
    From $448 per night (USD)

    VRBO

    Close to Galena, close to perfect. Premier get away. Three beautiful suites.

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    Pine Hollow is just a quick half mile drive to the town of Galena. When you turn into our driveway you will find your wo ...

    From $448 per night (USD)

    VRBO

    Details
  • Grafton Getaway-Cabin on 2 wooded acres just 1/2 mile from Main Street
    From $252 per night (USD)

    VRBO

    Grafton Getaway-Cabin on 2 wooded acres just 1/2 mile from Main Street

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    11

    Grafton Getaway - Cabin is a 2019 renovated home originally built in 1900. The long driveway crosses a spring-fed creek ...

    From $252 per night (USD)

    VRBO

    Details
  • 3 Bedroom Home Away From Home
    From $85 per night (USD)

    VRBO

    3 Bedroom Home Away From Home

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Totally refurbished home with central AC and heat. Primarily set up for temporary contractors and includes all basic uti ...

    From $85 per night (USD)

    VRBO

    Details
  • Half a mile from everything in the heart of Evanston, Illinois
    From $416 per night (USD)

    Expedia

    Half a mile from everything in the heart of Evanston, Illinois

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...

    From $416 per night (USD)

    Expedia

    Details
  • River Retreat - Waterfront Cottage in Starved Rock Country
    From $436 per night (USD)

    VRBO

    River Retreat - Waterfront Cottage in Starved Rock Country

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to River RetreatCottages at Heron’s Landing • Heritage Harbor Marina Resort • Managed by Harbor Inn Vacation Ren ...

    From $436 per night (USD)

    VRBO

    Details
  • 360 Degree Rooftop Views - Perfect for Eagle Watching
    From $379 per night (USD)

    Expedia

    360 Degree Rooftop Views - Perfect for Eagle Watching

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    SUNSHINE TERRACEAs the name implies, Sunshine Terrace catches a great view from multiple balconies including your own pr ...

    From $379 per night (USD)

    Expedia

    Details
  • Enjoy Your Vacation On Lake Pistakee Of The Chain
    From $265 per night (USD)

    VRBO

    Enjoy Your Vacation On Lake Pistakee Of The Chain

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Looking for that vacation home feel on the beautiful Chain O'Lakes? Our clean cozy cabin is perfect for a couple, or fam ...

    From $265 per night (USD)

    VRBO

    Details
  • Lakefront home Wonder Lake IL - Close to Lake Geneva and Twin Lakes Wi
    From $694 per night (USD)

    Expedia

    Lakefront home Wonder Lake IL - Close to Lake Geneva and Twin Lakes Wi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    This must be the place and the time is now to book that special getaway with family and friends. The house is situated r ...

    From $694 per night (USD)

    Expedia

    Details
  • Rockford Retro Revival • Indoor Pool + Arcade Fun!
    From $808 per night (USD)

    VRBO

    Rockford Retro Revival • Indoor Pool + Arcade Fun!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    19

    Summary: Step into a bold, retro-inspired retreat packed with fun! Dive into the indoor pool, unwind in the hot tub, an ...

    From $808 per night (USD)

    VRBO

    Details
  • New Humble Home! - Near Six Flags & Naval Base!!
    From $433 per night (USD)

    Expedia

    New Humble Home! - Near Six Flags & Naval Base!!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our beautiful and welcoming home, perfect for families and groups visiting the area! Our convenient location ...

    From $433 per night (USD)

    Expedia

    Details
  • ☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆
    From $258 per night (USD)

    VRBO

    ☆Spacious 3bdr near 6 Flags-Naval Base-Casino☆

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Relax with the whole family at this beautiful 3 bedroom house Self check in / No contact (smart locks). The home is lo ...

    From $258 per night (USD)

    VRBO

    Details
  • Mississippi River House
    From $206 per night (USD)

    Expedia

    Mississippi River House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy Riverfront Island house overlooking the Mississippi River. House is on the 2nd floor with two queen size beds. A v ...

    From $206 per night (USD)

    Expedia

    Details
  • 3bd/3.5ba, Bright & Spacious, Fab Screened Porch,  Fireplace
    From $467 per night (USD)

    VRBO

    3bd/3.5ba, Bright & Spacious, Fab Screened Porch, Fireplace

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    <p><strong>Bluffwood Belle, Galena IL</strong></p> <p><strong>Entire Home Vacation Rental, 3 Bed, 3 Bath, 8 Person Occu ...

    From $467 per night (USD)

    VRBO

    Details
  • *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
    From $579 per night (USD)

    Expedia

    *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located c ...

    From $579 per night (USD)

    Expedia

    Details
  • 2 Bedroom Cul De Sac Cottage in Town
    From $200 per night (USD)

    VRBO

    2 Bedroom Cul De Sac Cottage in Town

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    2 bedroom ranch home conveniently located in a quiet area of town within walking distance of parks and dining. Open con ...

    From $200 per night (USD)

    VRBO

    Details
  • PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
    From $340 per night (USD)

    Expedia

    PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Our house is perfect for a small group of friends or family looking for a clean, accessible place. It contains 3 bedroom ...

    From $340 per night (USD)

    Expedia

    Details
  • 30 West · The View · Scenic Escape near Fairground
    From $138 per night (USD)

    VRBO

    30 West · The View · Scenic Escape near Fairground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Step into 30 West · The View, a bright and stylish suite overlooking downtown Du Quoin. Wake up to sunlight streaming th ...

    From $138 per night (USD)

    VRBO

    Details
  • Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
    From $467 per night (USD)

    Expedia

    Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Charming and cozy, Trail’s End is uniquely positioned in one of the most beautiful corners of the Galena Territory. It ...

    From $467 per night (USD)

    Expedia

    Details
  • Hilltop Retreat, a modernly-rustic getaway!
    From $316 per night (USD)

    VRBO

    Hilltop Retreat, a modernly-rustic getaway!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    At the top of the Shawnee Wine Trail, amidst the Shawnee National Forest, and tucked away in the country, is your next c ...

    From $316 per night (USD)

    VRBO

    Details
  • Modern Comfort Meets Natural Beauty: Your Perfect Getaway Near Starved Rock!
    From $242 per night (USD)

    Expedia

    Modern Comfort Meets Natural Beauty: Your Perfect Getaway Near Starved Rock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    9

    Modern Comfort Meets Natural Beauty: Your Perfect Getaway Near Starved Rock! Nestled behind Grand Bear Resort and Water ...

    From $242 per night (USD)

    Expedia

    Details
  • Historic house, 1.5miles from U of I University
    From $503 per night (USD)

    VRBO

    Historic house, 1.5miles from U of I University

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Willis House is located in a safe, older neighborhood, with tree lined streets and deeply shaded yards. Great shopping ...

    From $503 per night (USD)

    VRBO

    Details
  • 2 BR W/ Washer Dryer,  Fireplace, Close To It All, Monthly Stays Welcome
    From $286 per night (USD)

    Expedia

    2 BR W/ Washer Dryer, Fireplace, Close To It All, Monthly Stays Welcome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Our cozy condo is the ideal place to feel at home. Affordable, convenient, close to Downers Grove, Wheaton, Oakbrook, Do ...

    From $286 per night (USD)

    Expedia

    Details
  • 30 West · The Den ·Downtown Hideaway near Fairground
    From $138 per night (USD)

    VRBO

    30 West · The Den ·Downtown Hideaway near Fairground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Welcome to 30 West · The Den, a modern downtown hideaway in the heart of Du Quoin. Just minutes from the State Fairgroun ...

    From $138 per night (USD)

    VRBO

    Details
  •  Hidden Gem SLEEPS 10+!  Children & Pets welcomed!
    From $511 per night (USD)

    Expedia

    Hidden Gem SLEEPS 10+! Children & Pets welcomed!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Unique to Northern Illinois, this Spanish style Villa boasts five patios, a furnished balcony, a gazebo for the perfect ...

    From $511 per night (USD)

    Expedia

    Details
  • Peter Ray House
    From $224 per night (USD)

    VRBO

    Peter Ray House

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 150-year-old story and a half house is approximately 1200 square feet, with central air and three TVs. It has a fro ...

    From $224 per night (USD)

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  • On The Golf Course, Outdoor Kitchen, Hot Tub and So Much More!
    From $1319 per night (USD)

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    On The Golf Course, Outdoor Kitchen, Hot Tub and So Much More!

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Wonderful large home located on the South Course of Eagle Ridge. 6 Bedrooms all with en suite baths. Outdoor kitchen o ...

    From $1319 per night (USD)

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  • Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
    From $1088 per night (USD)

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    Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Located inside one of the iconic Wrigley Rooftops, and just a few steps away from Wrigley Field, this apartment offers a ...

    From $1088 per night (USD)

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  • Medley Manor Resort Sleeps over 65 , it has 7 Large bathrooms & game room!
    From $717 per night (USD)

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    Medley Manor Resort Sleeps over 65 , it has 7 Large bathrooms & game room!

    Bedrooms:
    7
    Bathrooms:
    14
    Sleeps:
    80

    Medley Manor Resort is a licensed boutique hotel that only books to one host family or group. Medley Manor is never shar ...

    From $717 per night (USD)

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  • A Luxury Family Mill Creek Lake Retreat
    From $1106 per night (USD)

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    A Luxury Family Mill Creek Lake Retreat

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    A Complete Lakeside Experience! Better than a trip to Kentucky/Tennessee/Wisconsin/Michigan. This house is in the crossr ...

    From $1106 per night (USD)

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  • Home is on the original 1926-1930 Route 66 alignment
    From $181 per night (USD)

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    Home is on the original 1926-1930 Route 66 alignment

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    This house is located 34 miles south of Springfield, Illinois; 85 miles North of St. Louis, Missouri; 8 miles off I-55 i ...

    From $181 per night (USD)

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  • 4bd 4ba spacious home w/hot tub-seasonal, pool table, firepit, Pet Friendly
    From $646 per night (USD)

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    4bd 4ba spacious home w/hot tub-seasonal, pool table, firepit, Pet Friendly

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    4 bedroom, 4 bath home with pool table, (hot tub available April 1 - 10/31, not open during the winter months), main lev ...

    From $646 per night (USD)

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  • 2 bed 2 bath Near Lake Access Hunt & Gather Lodge
    From $227 per night (USD)

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    2 bed 2 bath Near Lake Access Hunt & Gather Lodge

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located near the shores of Rend Lake, Hunt and Gather Lodge is an inviting 1,000 sq ft, 2 bedroom, 2-bathroom home that' ...

    From $227 per night (USD)

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  • Longwood - Wood Burning Fireplace - Hot Tub - Pool Table - Arcade Game
    From $590 per night (USD)

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    Longwood - Wood Burning Fireplace - Hot Tub - Pool Table - Arcade Game

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Our Longwood home is 10 minutes to the GTA Owners Club (we provide proximity cards for free access) and 15 minutes to Do ...

    From $590 per night (USD)

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  • Amazing Golf Views, Fireplace & Pool Access!
    From $183 per night (USD)

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    Amazing Golf Views, Fireplace & Pool Access!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Our Poplar Ridge home is approximately 7 miles or 15 minutes to Downtown Galena. Over 400 5* Reviews! This home is NOT ...

    From $183 per night (USD)

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  • >DARTS>  Outdoor Hot Tub, Screened Porch, Fireplace, Dog Friendly!
    From $378 per night (USD)

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    >DARTS> Outdoor Hot Tub, Screened Porch, Fireplace, Dog Friendly!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Our Golfside Haven house is approximately 8 miles or 13 minutes to Downtown Galena and just 3.5 miles to the GTA Owners ...

    From $378 per night (USD)

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  • 5 BR en suite with firepit, hot tub,and game room.
    From $571 per night (USD)

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    5 BR en suite with firepit, hot tub,and game room.

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    As you walk into this spacious 5 bedroom home, each with it's own private bath, you will instantly feel a sensation of c ...

    From $571 per night (USD)

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    Details
  • Beautiful Makanda Cabin in Shawnee National Forest
    From $365 per night (USD)

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    Beautiful Makanda Cabin in Shawnee National Forest

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sat atop a scenic hillside and overlooking a breathtaking meadow, this 2-bedroom, 1.5-bath Makanda vacation rental is th ...

    From $365 per night (USD)

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  • Private 2 Acres! Fire Pit, Hot Tub, Game Room AND Movie Room, Bunk Room!
    From $582 per night (USD)

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    Private 2 Acres! Fire Pit, Hot Tub, Game Room AND Movie Room, Bunk Room!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to Timber Ridge, nestled in the woods on four secluded acres surrounded by green space. We are NOT Pet-Friendly! ...

    From $582 per night (USD)

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  • Historic Beauty Steps to Main St - Fireplace, 3 Season Room, Record Player
    From $292 per night (USD)

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    Historic Beauty Steps to Main St - Fireplace, 3 Season Room, Record Player

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    This Beautiful, Historical and Updated home is smack dab downtown Galena. This Preservation Award-winning home was buil ...

    From $292 per night (USD)

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  • Private 2 acres, Huge Deck, Hot Tub, Fitness Room, Movie Room & Pool Table
    From $641 per night (USD)

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    Private 2 acres, Huge Deck, Hot Tub, Fitness Room, Movie Room & Pool Table

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Powderhorn Gap is 7 minutes from the GTA Owners Club (we provide proximity for free access) and 17 minutes to Downtown ...

    From $641 per night (USD)

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  • Prestigious Trillium Lane*Hot Tub*2 Fireplaces*Pool Table*Fire Pit* Sleeps 14
    From $815 per night (USD)

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    Prestigious Trillium Lane*Hot Tub*2 Fireplaces*Pool Table*Fire Pit* Sleeps 14

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Only 3 miles to the GTA Owners Club and 8 miles to Downtown Galena. This home is NOT pet-friendly. This 5200 square foo ...

    From $815 per night (USD)

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  • Amazing Tree Top Views-Outdoor Hot Tub, Fire Pit, Pool Table, Access 2 Pools!
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    Expedia

    Amazing Tree Top Views-Outdoor Hot Tub, Fire Pit, Pool Table, Access 2 Pools!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Our Eagle Lane home is 1.5 miles from the GTA Owners Club and just 15 minutes from downtown Galena. This home is NOT pe ...

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  • Huge 4BR*Outdoor Hot Tub*2 Fireplaces*Pool Table*Great Value*
    From $373 per night (USD)

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    Huge 4BR*Outdoor Hot Tub*2 Fireplaces*Pool Table*Great Value*

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This home is approximately 8 miles or 15 minutes from Downtown Galena. This home is NOT pet-friendly. You must be 25 or ...

    From $373 per night (USD)

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  • Woodland Vista Retreat on Creekwood - Patio, Grill, Fireplace & Dog Friendly
    From $183 per night (USD)

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    Woodland Vista Retreat on Creekwood - Patio, Grill, Fireplace & Dog Friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Woodland Vista Retreat– a cozy villa that is a 15 minute beautiful drive to Downtown Galena. Please note: thi ...

    From $183 per night (USD)

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  • Firelit evenings @ Grand Galena Retreat w/Whiskey Room, Fireplace & Hot Tub
    From $904 per night (USD)

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    Firelit evenings @ Grand Galena Retreat w/Whiskey Room, Fireplace & Hot Tub

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    The GTA Owners Club is just 4 minutes away, and Downtown Galena is only 15 minutes away. This home is NOT pet-friendly. ...

    From $904 per night (USD)

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  • Outdoor Hot Tub, Pool Table, Huge Fire Pit - Close 2 Pools!
    From $548 per night (USD)

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    Outdoor Hot Tub, Pool Table, Huge Fire Pit - Close 2 Pools!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to Fore Augusta Drive. We are 4 minutes from the GTA Owners Club (pools, fitness center, etc.) and 15 minutes t ...

    From $548 per night (USD)

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    Details
  • Cozy Getaway - 3 King Beds w/en suite baths, Hot Tub, Pool Table, Arcade Game
    From $319 per night (USD)

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    Cozy Getaway - 3 King Beds w/en suite baths, Hot Tub, Pool Table, Arcade Game

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Bayward is 3 miles from the GTA Owners Club and 7 miles to Downtown Galena. This home is NOT pet-friendly. *Golf Benef ...

    From $319 per night (USD)

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  • Luxury Home: Heated Pool, Hot Tub (Open!), 4Kings
    From $1427 per night (USD)

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    Luxury Home: Heated Pool, Hot Tub (Open!), 4Kings

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    16

    **Hot Tub/Spa Open Year-Round • Heated Saltwater Pool Open NOW** Discover the ultimate luxury getaway at this newly ren ...

    From $1427 per night (USD)

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  • Step In To the Mediterranean
    From $619 per night (USD)

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    Step In To the Mediterranean

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Please NOTE: The heated Estate Pool (shared by all our guests) will be open as long as weather permits. The private hot ...

    From $619 per night (USD)

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  • Spacious-Hot Tub-Pool Table-Screen Porch-6 Bedroom-6 Bathroom
    From $605 per night (USD)

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    Spacious-Hot Tub-Pool Table-Screen Porch-6 Bedroom-6 Bathroom

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    The Gathering Place is a modern, spacious 6 bedroom/6 bathroom home that accommodates up to 14 people. We are family fr ...

    From $605 per night (USD)

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  • Adorable studio unit with full kitchen
    From $116 per night (USD)

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    Adorable studio unit with full kitchen

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This newly renovated one bedroom unit features a full kitchen, brand new appliances, laundry on site, massive spa like s ...

    From $116 per night (USD)

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  • Chicago's Hidden Treasure, \EVANSTON, IL\
    From $421 per night (USD)

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    Chicago's Hidden Treasure, \"EVANSTON, IL\"

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...

    From $421 per night (USD)

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  • An Inviting Retreat!
    From $330 per night (USD)

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    An Inviting Retreat!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Red AnchorCottages at Heron’s Landing • Heritage Harbor Marina Resort • Managed by Harbor Inn Vacation Rental ...

    From $330 per night (USD)

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  • A Quaint, Inviting Retreat
    From $241 per night (USD)

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    A Quaint, Inviting Retreat

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Harbor Master VillaThe Villas at Heron’s Landing • Heritage Harbor Marina Resort • Managed by Harbor Inn Vaca ...

    From $241 per night (USD)

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  • Gem Location on the River!
    From $298 per night (USD)

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    Gem Location on the River!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Rollin’ on the RiverCottages at Heron’s Landing • Heritage Harbor Marina Resort • Managed by Harbor Inn Vacat ...

    From $298 per night (USD)

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  • A Quaint, Inviting Retreat
    From $238 per night (USD)

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    A Quaint, Inviting Retreat

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Huck FinnThe Cottages at Herons Landing Neighborhood • Heritage Harbor Marina Resort • Managed by Harbor Inn ...

    From $238 per night (USD)

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  • Panoramic Views of the Illinois Waterway
    From $247 per night (USD)

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    Panoramic Views of the Illinois Waterway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Our Happy Place on the RiverCottages at Herons Landing Neighborhood • Heritage Harbor Marina Resort • Managed ...

    From $247 per night (USD)

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  • Prime location on the river.
    From $326 per night (USD)

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    Prime location on the river.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Serenity NowCottages at Heron’s Landing • Heritage Harbor Marina Resort • Illinois River • Managed by Harbor ...

    From $326 per night (USD)

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  • Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory
    From $174 per night (USD)

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    Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Beautifully decorated living room kitchen combo with high ceilings, sky light and wood burning fireplace. Upper level b ...

    From $174 per night (USD)

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  • Your Vacation Paradise!
    From $239 per night (USD)

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    Your Vacation Paradise!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Captain’s QuartersCottages at Heron’s Landing • Heritage Harbor Marina Resort • Professionally Managed by Har ...

    From $239 per night (USD)

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  • Star Gaze on your Private Second Level Deck!
    From $465 per night (USD)

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    Star Gaze on your Private Second Level Deck!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to This Must Be The PlaceCottages at Heron’s Landing • Heritage Harbor Marina Resort • Illinois River • Managed ...

    From $465 per night (USD)

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  • Escape the city to quiet and picturesque Golden Eagle, IL..
    From $327 per night (USD)

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    Escape the city to quiet and picturesque Golden Eagle, IL..

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Great river road is a panorama of colors in the fall! Winter the Eagles arrive! Data speeds up to 25 megabytes! **COV ...

    From $327 per night (USD)

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  • Havisham House Suite 88 - 3 bedroom, 2 bath, wine trail, bourbon bar -Alto Pass
    From $309 per night (USD)

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    Havisham House Suite 88 - 3 bedroom, 2 bath, wine trail, bourbon bar -Alto Pass

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Newly renovated suite in historic 1800s Alto Pass Milling Co building. Private, spacious and very clean. Upstairs from n ...

    From $309 per night (USD)

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  • Havisham Bourbon Bar - Suite 18 - private, spacious, wine trail apartment
    From $271 per night (USD)

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    Havisham Bourbon Bar - Suite 18 - private, spacious, wine trail apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Newly renovated suite in historic 1800s Alto Pass Milling Co building. Private, spacious and very clean. Upstairs from n ...

    From $271 per night (USD)

    Expedia

    Details