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Columbia Area Rentals

From $100 per night (USD)
VRBO
Catskill Cottage, Walk to Downtown & River Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled just steps away from the heart of Main Street, the Catskill Cottage beckons you to experience the charm of Upsta ...
From $100 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Modern hilltop chalet-style cabin @ Copake Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to @hilltopchalet_copakelake ! Kick back and relax in this calm, stylish, modern cabin. Indoor/Outdoor living p ...
From $304 per night (USD)
VRBO
From $159 per night (USD)
VRBO
the suite @ gallatin farmstead - private, bucolic, serene setting
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
A 675 sq ft. fully private suite with your own entrance in an early American eyebrow colonial. The well appointed space ...
From $159 per night (USD)
VRBO
From $585 per night (USD)
VRBO
Secluded home pool and hot tub Kinderhook. Ski slopes only 35 minutes away!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Come relax in this calm, stylish space. Located at the top of the hill above Kinderhook lake, this house offers a charm ...
From $585 per night (USD)
VRBO
From $630 per night (USD)
VRBO
The Peary Homestead
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome! This is a fully furnished Gothic Style home in Germantown, NY. It was built in 1840 by the sea captain Robert P ...
From $630 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Renovated Chatham Home ~ Half Mi to Downtown!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Discover a quiet retreat in this stunning 4-bedroom, 2.5-bath vacation rental in Chatham, NY. Unwind and enjoy the charm ...
From $353 per night (USD)
Expedia
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Expedia
Chic Scandinavian Country Retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful country home in East Chatham. Set in a lush, expansive setting on 4 acres ...
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Expedia
From $234 per night (USD)
VRBO
A Ghent Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to A Ghent Getaway. Relax with the whole family or enjoy a romantic getaway at this newly renovated home. This b ...
From $234 per night (USD)
VRBO
From $214 per night (USD)
VRBO
Hilltop House
Bedrooms:
5
Bathrooms:
4
Sleeps:
9
About this space Hilltop House is the perfect get away for your family! Located on 15 acres, it is the best place to enj ...
From $214 per night (USD)
VRBO
From $9540 per night (USD)
VRBO
The Brooks Buy Out, Wedding Groups Inquire Today!
Bedrooms:
24
Bathrooms:
26
Sleeps:
60
Summary: Hosting an event at Catamount or Taconic Ridge Farms? Direct your guests to The Brooks Motel, located directly ...
From $9540 per night (USD)
VRBO
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VRBO
Private historic Hudson home on 20 acres with pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Secluded and surrounded by nature, the Jedediah Link House is an incredible period home nestled on a bucolic road outsid ...
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VRBO
$Mountain Luxury Retreat-Amazing Views\/Saltwater Pool\/Family Friendly\/Berkshires$
From $995 per night (USD)
VRBO
Mountain Luxury Retreat-Amazing Views\/Saltwater Pool\/Family Friendly\/Berkshires
Bedrooms:
6
Bathrooms:
6
Sleeps:
10
Newly built in 2007, this home was designed with comfort, luxury and family fun in mind. The property is 12 acres in si ...
From $995 per night (USD)
VRBO
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VRBO
Cozy Creative 2BR Cottage in the Heart of Catskill
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space This pet-friendly cottage is perfect for anyone who wants a quiet getaway but still be within a few blo ...
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VRBO
From $180 per night (USD)
VRBO
Charming historic home surrounded by woods in Old Chatham
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our historic and charming home, tucked away on 50 acres of beautiful, serene woodland. Built in 1840, our 220 ...
From $180 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Sun-drenched upstate escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled among the trees with hillside views on a quiet country road 15 minutes outside of Hudson, Oak Hill is the perfec ...
From $250 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Book This Summer, Private Oasis, Pool + Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Summary: Nestled on a sprawling 16.5 private acres of land, this home offers a serene retreat from the outside world. As ...
From $606 per night (USD)
VRBO
From $283 per night (USD)
VRBO
Charming Catskill Getaway (Upstate NY!)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
"Discover the perfect blend of comfort and adventure in our spacious 3-bedroom Catskill hideaway. Nestled amidst breatht ...
From $283 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Near Skiing! Hot Tub, Wood Stove, Pool Table, & Theater Room. Pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berksh ...
From $290 per night (USD)
Expedia
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Expedia
Adventure Awaits in Ancram! Fishing, Hiking, Skiing, & so much more!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Discover your inner writer, create new memories, or simply unwind in the natural beauty of Ancram. This 1850s farmhouse ...
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Expedia
From $307 per night (USD)
VRBO
MJ’s Retreat Upstate NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax with the whole family at MJ's Retreat. The rustic modern ranch home is perfectly located in the beautiful mountain ...
From $307 per night (USD)
VRBO
From $300 per night (USD)
VRBO
CLASSIC COLUMBIA COUNTY FARMHOUSE
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Our place is a bright and airy 1893 farmhouse in the hamlet of Livingston, a scenic farm village in southern Columbia Co ...
From $300 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Welcome to the Blue Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our cottage is set in the quiet Hamlet of Claverack located 7 minutes away from buzzing Warren street restaurants in the ...
From $468 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Bespoke1920s Charm, Walk 2 Warren & Hot Tub [The Spring House]
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover 1920s elegance, while being within walking distance to vibrant Hudson and tranquil Oakdale Lake. Crafted by a l ...
From $439 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Spacious Cottage Retreat on Beautiful 2-Acres
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
About this space Featured by BUSINESS INSIDER as one of the 12 best Airbnbs near New York City this is your spot Enjoy ...
From $125 per night (USD)
Expedia
From $308 per night (USD)
VRBO
NEW - Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Peaceful Hudson Valley escape with large windows and stunning views. Bright and open. Internal balcony with beautiful ...
From $308 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Hudson Creekside Hideaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Freshly renovated, clean and close to Hudson this country home has creek frontage, sunset views over rolling hills in th ...
From $300 per night (USD)
Expedia
$Berkshire\/Hudson Valley Gather Family and Friends$
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VRBO
Berkshire\/Hudson Valley Gather Family and Friends
Bedrooms:
4
Bathrooms:
5
Sleeps:
6
Country charm with a modern vibe. A perfect place to gather family and friends. Set in picturesque Hillsdale, close to e ...
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VRBO
$4BR\/4.5BTH Historic-Modern Luxury\/downtown Hudson$
From $750 per night (USD)
Expedia
4BR\/4.5BTH Historic-Modern Luxury\/downtown Hudson
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
4 bedrooms all with private, en suite bathrooms - 3,000 sq ft Italianate style home is ideal for groups and families; up ...
From $750 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Hudson Valley and The Berkshires getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Welcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 be ...
From $568 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Summer rental 4Br - Big views + Pond, 10 acres bwtn Hudson and Great Barrington
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
In the foothills of the Berkshire Mountains on a quiet country road halfway between Great Barrington (15Min) and Hudson ...
From $270 per night (USD)
Expedia
From $78 per night (USD)
VRBO
Hudson valley and The Berkshires Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, ...
From $78 per night (USD)
VRBO
$Gemini House - 1892 Farmhouse w\/ Pool in Hudson$
From $700 per night (USD)
VRBO
Gemini House - 1892 Farmhouse w\/ Pool in Hudson
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Introducing Gemini House, a designer-renovated 1892 Farmhouse with 3 BR, 2.5 BA, dedicated work spaces, and a s ...
From $700 per night (USD)
VRBO
From $1302 per night (USD)
VRBO
River, Pool, Hot Tub, Treehouse, Guesthouse!
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
With your own private beach on the majestic Hudson River, this waterfront haven is the perfect get-away for family & fri ...
From $1302 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Private hot tub + Modern Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our fully furnished cottage located just five miles outside of Hudson, NY. Enjoy a private hot tub, outdoor f ...
From $166 per night (USD)
Expedia
$BLUSH: Boutique TINY home w\/ private spa. Walk to New York's cutest village.$
From $256 per night (USD)
VRBO
BLUSH: Boutique TINY home w\/ private spa. Walk to New York's cutest village.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy in at this PRIVATE OASIS & just steps from quintessential Main Street. Indulgences abound in this one-of-a-kind cur ...
From $256 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Hudson NY’S Country Serenity
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Forget your worries in this spacious, serene space, newly renovated open living and dining area that offers a relaxing a ...
From $161 per night (USD)
Expedia
$Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A\/C, 4 bdrms, 2 bath$
From $255 per night (USD)
VRBO
Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A\/C, 4 bdrms, 2 bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Berkshires-Great Natural Beauty, Culture, Outdoor Activities and Easy Highway Access. Close to Tanglewood. Special Offe ...
From $255 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Pet-Friendly Hudson Home Near Won Dharma Center!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A refreshing getaway to New York awaits at this bright 3-bedroom, 2.5-bath Hudson vacation rental! At this updated Victo ...
From $209 per night (USD)
Expedia
$Beebehill house\n\n$
From $500 per night (USD)
VRBO
Beebehill house\n\n
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautifully designed modern retreat is the perfect escape in the Hudson Valley. Kick back and relax in this calm, stylis ...
From $500 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Beautiful Hits Suite...Your home away from home suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
*WE DO NOT ADVERTISE ON CRAIGSLIST * MODERN ELEGANCE AWAITS YOU AT THIS 1 BEDROOM SUITE. Located in the heart of Sauger ...
From $217 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Remodeled Lakefront retreat with beautiful dock, lakeside firepit and more!!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Beautifully remodeled 4 bedroom lakefront home on 3 acres with private dock for paddle boarding, canoeing, swimming and ...
From $313 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Charming 3B2B apartment with In-Unit laundry in the center of marvelous Hudson
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Stay comfortably in Hudson at this 3-bedroom apartment. The adorable property features 3 queen beds, ensuring a cozy and ...
From $290 per night (USD)
VRBO
$The Lodge on the Lake\n$
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VRBO
The Lodge on the Lake\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Relax, revive, and rejuvenate. It's what we have been doing for many years at our house on Kinderhook Lake and now you c ...
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VRBO
From $507 per night (USD)
Expedia
Private Village Home in Catskill Splendor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
About this space Ideal for up to 8 guests, "The White House" sits in the village center, blending history and modernity. ...
From $507 per night (USD)
Expedia
From $896 per night (USD)
VRBO
Pool, HotTub, Firepit, Views @ Scenic Country Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
**New to VRBO - Follow us on IG @chillrockhouse and see link in bio to see reviews on other platforms. Stunning views, ...
From $896 per night (USD)
VRBO
From $615 per night (USD)
Expedia
Elegant Upstate Sanctuary on 20 Acres
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Mariposa Hill: a hidden gem in the Hudson Valley, approximately 2 hours from NYC. Set on 20 remarkable acres, ...
From $615 per night (USD)
Expedia
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VRBO
The Hudson House, Apt 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
La Maison, Hudson is a 3 story townhouse 2 blocks from Warren Street. Apartment 1 and 2 can be rented together or separa ...
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VRBO
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Expedia
La Maison, Hudson: apt 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
About this space La Maison, Hudson is a labor of love for our whole family. This beautiful little townhouse in central H ...
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Expedia
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VRBO
The Hudson House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
La Maison, Hudson is a 3 story townhouse 2 blocks from Warren Street. Apartment 1 and 2 can be rented together or separa ...
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VRBO
From $1890 per night (USD)
Expedia
Explore the Catskills & Hudson Valley from Emerick
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Emerick was built in 1913 and is set back from the road with large grassy areas for sun and several 100-year-old maple s ...
From $1890 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $267 per night (USD)
VRBO
$Three-level dog-friendly home with a washer\/dryer, central AC, yard, & patio$
From $159 per night (USD)
Expedia
Three-level dog-friendly home with a washer\/dryer, central AC, yard, & patio
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Colonial Classic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $159 per night (USD)
Expedia
$SRC-Hudson Valley\/Berkshires Cultural Corridor$
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Expedia
SRC-Hudson Valley\/Berkshires Cultural Corridor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
About this space We welcome you to explore the magic of Sunset Ridge Chalet (aka SRC). Ideally situated within the Hudso ...
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Expedia
$Sunny Pond by AvantStay | Secluded Estate w\/ Private Pond, Gym, & Movie Theater$
From $2310 per night (USD)
Expedia
Sunny Pond by AvantStay | Secluded Estate w\/ Private Pond, Gym, & Movie Theater
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Escape to the enchanting retreat of Sunny Pond, a charming estate nestled on a private pond among the serene forest of t ...
From $2310 per night (USD)
Expedia
$Organic Farm Retreat Minutes from Hudson\/Lake Taghkanic. Family & Dog Friendly!$
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VRBO
Organic Farm Retreat Minutes from Hudson\/Lake Taghkanic. Family & Dog Friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Our not-so-tiny-house on wheels is ideal for up to 6 guests and we welcome families with children. Full bath with double ...
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VRBO
From $425 per night (USD)
Expedia
Home in Germantown
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 3 bedroom, 2.5 bath has everything you need for the perfect retreat. Sunny rooms, cozy wood burning fireplace, and ...
From $425 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Relaxing 2BR Lakehouse by CozySuites
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Relax and unwind knowing our rentals are meticulously cleaned by a professional agency, ensuring a sanitized sp ...
From $196 per night (USD)
VRBO
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VRBO
Bohemian Glow, this cozy home is surrounded by birds and a wildlife habitat.
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
The song and view of a variety of birds in our surroundings is calming. You will enjoy the abundance of buzz, peaceful n ...
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VRBO
From $250 per night (USD)
VRBO
75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Watch the sunrise from the master bedroom, and watch the sunset from the deck! This sweet 1600 square foot ranch house ...
From $250 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Waterfront home with gym and spa access 1 Mile from HITS
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This recently remodeled home has four bedrooms and 1.5 bathrooms and is located on the same property as the al-new Water ...
From $400 per night (USD)
Expedia
From $155 per night (USD)
VRBO
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Sweet guest cottage perfectly located for exploring Columbia County, the Berkshires or simply lazing on the lawn with a ...
From $155 per night (USD)
VRBO
From $1044 per night (USD)
VRBO
Cool Vibes+Historic Spaces in the heart of Hudson!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A wide open door. Three magical floors. And a love infused vibe. Right in the heart of Hudson. 2500 square feet. 4 bed ...
From $1044 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Downtown Hudson Apartment: Walk to Cafes & River!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Embark on a relaxing getaway in upstate New York at this 2-bed, 1-bath vacation rental in Hudson! This walkable haven is ...
From $325 per night (USD)
VRBO
From $737 per night (USD)
Expedia
Cambridge Hill Farmhouse Swimming pond, Sauna, & Artist Studio
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Introducing Cambridge Hill Farmhouse, a storybook Hudson Valley rental property. Perched above the Valleys of Copake an ...
From $737 per night (USD)
Expedia
From $474 per night (USD)
VRBO
Dreamy 6 Bedroom House, Come Enjoy Hillsdale!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Summary: Welcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 6 co ...
From $474 per night (USD)
VRBO
From $826 per night (USD)
Expedia
NEW: Unparalleled Hudson River Views in Hudson
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Highlights: If your wish list includes modern architecture, dreamy views, a nearby top tier town and a residence with hi ...
From $826 per night (USD)
Expedia
From $419 per night (USD)
VRBO
Apple Blossom Cottage by Evergreen Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Apple Blossom Cottage; Your Perfect Hudson Valley Escape -Newly renovated & thoughtfully designed mid century retreat -G ...
From $419 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Beautifully renovated and decorated farmhouse on quiet Hillsdale country road
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautifully renovated and decorated farmhouse on quiet back country road in much sought after Hillsdale. Three bedrooms. ...
From $430 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Eclectic Escape of Germantown
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Eclectic Escape is a brand new custom-built home in the high hills of Germantown, NY. The professionally designed custom ...
From $573 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
This centrally located home is just a few minutes walk to Main St where you can explore the historic Catskill city and f ...
From $200 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Farmhouse with undisturbed, magical views and european decoration
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Germantown Gem with Unparalleled Views Exceptional farmhouse nestled in the heart of Germantown. This unique, classic fa ...
From $400 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Hudson Valley private 70's-style cabin on five acres, five minutes to town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
On 5 private, wooded acres, but only 2 miles from Millerton, one of the cutest towns in the Hudson Valley. Amazing food, ...
From $118 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Riverview Retreat located on the Hudson River in Upstate NY
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming studio apartment nestled by the Hudson River, boasting breathtaking views. This renovated garage-turned-hideawa ...
From $130 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Hudson Valley Restored Historic Victorian Fall Rental Deal!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
5 bedroom (queens)/3.5 bath completely restored historic home in the walkable hamlet of Malden (in the town of Saugertie ...
From $399 per night (USD)
Expedia

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