Litchfield Area Rentals
- From $656 per night (USD)
VRBO
Mohawk Manor ~ 5 min to Skiing at Mohawk Mtn!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Mohawk Manor is a spacious and chic escape located just minutes from the hamlet of Cornwall and only 2.5 hours ...
From $656 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Litchfield Modern Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated farmhouse is complete with a gorgeous kitchen, new bathrooms and spacious bedrooms. A perfect spaci ...
From $298 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Spacious Woodbury Home w\/ Pool + Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Treat your family to an unforgettable mix of fun and relaxation when you make this Woodbury vacation rental the site of ...
From $595 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Cozy & Chic Cabin by the Lake, with access to private Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind from the daily stress at Deer Ridge Cabin. Bright and airy it has everything you need. Spend a day at the private ...
From $200 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Cozy 2-bedroom Cottage with Access to Bantam Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This cozy, quaint cottage with dedicated Bantam Lake access is the perfect getaway for nature enthusiasts, cyclists, wri ...
From $306 per night (USD)VRBO
- From $149 per night (USD)
VRBO
4 Bedroom Family Friendly Home in Riverton Paradise
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
In Historic Riverton Village: A 4-minute stroll to The Riverton General Store and everything else our charming village h ...
From $149 per night (USD)VRBO
- From $442 per night (USD)
VRBO
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to this newly renovated, freshly decorated, cozy waterfront retreat with breathtaking views of the lake! Nestle ...
From $442 per night (USD)VRBO
- From $426 per night (USD)
Expedia
Serene Salisbury Rental Home on 26 Acres w\/ Deck!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Relax, recharge, and repeat with a retreat to this serene Salisbury vacation rental! Featuring a prime location within w ...
From $426 per night (USD)Expedia
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VRBO
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage Ease is superbly nestled in rocky hills surrounding Highland lake, giving you a tree house feel. Mature gardens ...
Click For PricingVRBO
- From $200 per night (USD)
VRBO
Your Lake House this summer! Cozy cottage with full lake community amenities!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming cottage in Birch Groves lake community-walk to the beach, swim in the lake, tennis/pickleball just steps away! ...
From $200 per night (USD)VRBO
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VRBO
Litchfield County! Cozy & quiet, newly renovated 3 bdrm home near Lake Waramaug.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Kickback, relax, & listen to the babbling of Bee Brook in this newly renovated mid-century cottage. Located on 4 acres ...
Click For PricingVRBO
- From $850 per night (USD)
VRBO
The Chic Antique Retreat House
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Immerse yourself in rural Connecticut's charm with our lovingly restored 1700s farmhouse, nestled in the heart of Woodbu ...
From $850 per night (USD)VRBO
- From $496 per night (USD)
VRBO
Private Hilltop Cabin at Houndcliffe\n
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Start your next adventure and step into Houndcliffe, just 90 min from NYC and 10 min from downtown. Our picturesque 3-be ...
From $496 per night (USD)VRBO
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Expedia
Rustic House w\/ Heating + Pool
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Stay in this rustic house and live like a true local in Litchfield County. We're within walking distance to restaurants, ...
Click For PricingExpedia
- From $275 per night (USD)
VRBO
The Doctor's 1781 House on the Litchfield Green
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Doctor’s 1781 House on the Green in the Litchfield Historic District, a registered lamdmark. We are thril ...
From $275 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Farm Valley Cottage + 60 ft Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Country getaway, light filled 3-bedroom cottage, private 60' pool with sweeping farm valley views, plus guest studio. Ne ...
From $650 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Lakeview property in private community. Lake & beach access. Swim\/Kayak all day!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Swim, Kayak and Fish all day. Amazing sunsets and millions of stars. Make s’mores at the fire pit. Play games, read, or ...
From $225 per night (USD)VRBO
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Expedia
New Fairfield Vacation Rental w\/ Lake Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Connecticut countryside when you stay at 'Anthony's Hill,' a New Fairfield vacation rental! This 3-bedroo ...
Click For PricingExpedia
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VRBO
Litchfield cozy farmhouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely farmhouse centrally located on main road in Bantam, part of Litchfield, CT. Litchfield County is great for the go ...
Click For PricingVRBO
- From $453 per night (USD)
Expedia
Direct Lake Front Home, Games, Kayaks & Relaxation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Candlewood Shore! Escape to the tranquility of our picturesque lakehouse, where relaxation meets adventure. N ...
From $453 per night (USD)Expedia
- From $94 per night (USD)
VRBO
Getaway for a weekend!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for a quaint and cozy little place to stay in the city of Winsted Ct.? Just relax and enjoy this one bedroom, on ...
From $94 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Connecticut Retreat: Steps to Historic Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the perfect getaway at this charming 2-bedroom, 1-bathroom vacation rental townhome in Morris, CT! Nestled in ...
From $243 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Charming lakeside cottage and guest cottage with spectacular views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
*** WE WILL NOT BE RENTING FOR THE SUMMER SEASON AT THIS TIME*** Charming 3-bedroom lakefront furnished cabin and 2-bed ...
From $700 per night (USD)VRBO
- From $800 per night (USD)
VRBO
5 bedroom house with a dock on Candlewood Lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Newly renovated 5 bedroom, 2 bathroom house with kitchen (brand new appliances), dining area, 2 living rooms, pool table ...
From $800 per night (USD)VRBO
- From $632 per night (USD)
VRBO
Modern, cozy 3 bedroom lakeside cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of Litchfield County, this contemporary Cape Cod style cottage provides the perfect countryside get ...
From $632 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Cozy remodeled cottage. Close to town, vineyards, restaurants, and farms.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Light and airy, freshly remodeled cottage. Just two minutes from historical Litchfield which boasts shopping, restaurant ...
From $264 per night (USD)VRBO
- From $338 per night (USD)
VRBO
New - Berkshire Fall Getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Take a break from the city and escape to New England to rest and relax in this charming Colebrook vacation rental. A c ...
From $338 per night (USD)VRBO
- From $294 per night (USD)
Expedia
West Hill Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Follow us | @westhillcabin Rest and reconnect with family and friends at West Hill Cabin, a log home located in the Lit ...
From $294 per night (USD)Expedia
- Click For Pricing
VRBO
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This home provides the perfect mix of 1700s farmhouse charm with modern upgrades to accommodate your every need. There ...
Click For PricingVRBO
- From $500 per night (USD)
Expedia
Spacious lake house with a hot tub, fire pit, dock & only 80 minutes from NYC!\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
About the Space Welcome to Candlewood Lake! Our beautiful garden getaway is perfect for a family getaway to relax, unw ...
From $500 per night (USD)Expedia
- From $311 per night (USD)
VRBO
New Milford Home on Candlewood Lake w\/ Dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this stunning 3-bedroom, 3-bathroom vacation rental house nestled in New Milford, CT. Relax and enjoy full Can ...
From $311 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lake, beach, clubhouse, basketball, tennis, marina and playground all within a 5 minute walk. Located in Candlewood Isl ...
From $349 per night (USD)Expedia
- From $770 per night (USD)
VRBO
VillaRosa-Mohawk Mountain
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Views and nature abound in this little piece of paradise. Sit back, relax and enjoy all that Litchfield County has to of ...
From $770 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Peaceful Lakeville Retreat Located Within Minutes to Local Schools
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Nestled off of a long driveway at the end of a cul-de-sac, this cozy house provides a private and peaceful stay in Lakev ...
From $286 per night (USD)VRBO
- From $470 per night (USD)
VRBO
Artistic concered barn
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
This 1800's barn has been renovated into a modern yet whimsical home two family home. Wandering Peacock is the main hous ...
From $470 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Academic rental 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy the fall and winter in this family lake home. Enjoy apple picking, farms for pumpkin picking and relaxing by the l ...
From $325 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Tranquil Litchfield Connecticut Retreat\".
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our charming two-bedroom, one-bathroom property nestled on a spacious half-acre lot in the picturesque town o ...
From $200 per night (USD)VRBO
- Click For Pricing
VRBO
Luxurious 5 BR mansion in the heart of Washington, CT
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
This estate was featured in the New England Home Magazine ("Dressed to Impress"). Relax with the whole family at this pe ...
Click For PricingVRBO
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VRBO
New Fairfield Vacation Rental w\/ Lake Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Relaxed living awaits at this charming 1-bedroom, 1-bathroom vacation rental apartment in New Fairfield, CT. Located jus ...
Click For PricingVRBO
- Click For Pricing
Expedia
Rustic Three bedroom , 2 full bath Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a rustic Three bedroom , 2 full bath Bungalow in lower Litchfield county **LOOKING for A month as the Minimum st ...
Click For PricingExpedia
- From $1059 per night (USD)
VRBO
5 bedroom, 14 acre private estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This is a renovated house situated on a 14 acre in Litchfield County, CT. This is a 5 bedroom (1 king size bed, 3 queen ...
From $1059 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Modern cabin with fireplace and beautiful views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Enjoy a peaceful retreat in New Milford at this modern, comfortable cabin. A spacious front porch with ...
From $400 per night (USD)VRBO
- From $695 per night (USD)
VRBO
Historic Litchfield County Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
New to VRBO but a 5 STAR SUPERHOST! Kick back and relax in this calm, stylish 1910 historic home (10-12 guests). You’l ...
From $695 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Gorgeous Year-Round Mid-Century Lake House Gem on sought after Lake Waramaug!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Step back in time at this newly furnished Mid-Century Jewel Box of a Gem, and take in breathtaking views of prestigious ...
From $500 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Cozy Fall Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy cabin in South Kent. Relax by the fire, visit the nearby farms to pickup some incredible produce to cook, go for a ...
From $265 per night (USD)VRBO
- From $210 per night (USD)
VRBO
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fall asleep to the sound of the rushing brook in this beautifully restored, 2 bedroom, 1.5 bath log home. The cabin sits ...
From $210 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Cozy Lake Cottage with Hot Tub, Views, Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Let the sun shine in! Bright and cozy cottage overlooking beautiful Candlewood Lake is perfect for all season getaways. ...
From $300 per night (USD)VRBO
- From $828 per night (USD)
VRBO
Retreat in Style: Luxury for Family & Friends
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Stay in our Entertainer's home, blending history and modern luxury. Gather and create unforgettable memories with family ...
From $828 per night (USD)VRBO
- Click For Pricing
VRBO
Country Winter Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come take a winter getaway in idyllic Litchfield County. A winter and spring resting place, a sanctuary in the quiet wo ...
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Expedia
Farm Historic House 1789
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm and history of the Farm Historic House, built in 1789. Explore its rich heritage and discover the s ...
Click For PricingExpedia
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VRBO
Spacious 3-bedroom house with large patio and sprawling yard.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the fresh air in this comfortable 3-bedroom house on 2.8 acres. Relax on the deck while you soak in the sun and ta ...
Click For PricingVRBO
- From $304 per night (USD)
VRBO
Gather your family at this country estate
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
This property is set in the countryside across from Judd Farm Day Camp this is one of the properties of "Watertown Count ...
From $304 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Spectacular Lake front house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to the prestigious Candlewood Lake area, where there is always something to do for the entire family. T ...
From $234 per night (USD)VRBO
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Expedia
Berkshire farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Cozy modern farmhouse on pristine private acherage. Ideal for groups and families. Southern Berkshire gem. 4 bedrooms, ...
Click For PricingExpedia
- From $166 per night (USD)
VRBO
Cozy Fall and ski rental nestled in a gated community in the woods.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Love to ski and looking for a cozy winter rental? Then I have the home for you. Get away to the scenic Litchfield Hills ...
From $166 per night (USD)VRBO
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Expedia
Cheerful 3 bedroom Kent getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Kick back and relax in this calm, stylish space. The Cape is close to everything the town of Kent has t ...
Click For PricingExpedia
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VRBO
NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Equipped with essentials such as air conditioning, cleaning products, cooking basics, and a dedicated workspace. Guests ...
Click For PricingVRBO
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Expedia
Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the ful ...
Click For PricingExpedia
- From $116 per night (USD)
VRBO
Litchfield - Hot Tub - Mohawk Mountain - Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. E ...
From $116 per night (USD)VRBO
- From $971 per night (USD)
Expedia
BlackWoods Old Country Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Escape to your own private retreat in this cozy and chic house nestled in the heart of the tranquil woods. This enchanti ...
From $971 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Modern Ranch Retreat in Hudson Valley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover a contemporary and recently renovated retreat in the charming village of Millerton, NY. You can relax in this i ...
From $340 per night (USD)VRBO
- From $475 per night (USD)
Expedia
The Long View of Candlewood Lake
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the beautiful and peaceful Long View of Candlewood Lake! A charming home for you and your family to enjoy a ...
From $475 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Litchfield County Country Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Situated on 6 acres on the property of the beautiful New Milford Tennis And Swim Club. The home is private and separate ...
From $250 per night (USD)VRBO
- From $3121 per night (USD)
VRBO
Spacious Litchfield County Lake House steps away from Lake Waramaug Perfect...
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Lakeside Sensation Spaci ...
From $3121 per night (USD)VRBO
- From $410 per night (USD)
VRBO
Sun-Soaked Chalet Near Lake and Ski Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Relax with the whole family on a country getaway in a bucolic lake community! Soaring ceilings and high ...
From $410 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Renovated, one level home in an excellent location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house h ...
From $249 per night (USD)Expedia
- From $463 per night (USD)
VRBO
The Art House: 5-Acre Private Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Situated on 5 acres, "The Art House" is the perfect place for those looking to relax and unwind, as well as to explore a ...
From $463 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Cozy family and pet friendly 3BR Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Relax with the whole family at this peaceful place to stay just steps from Heritage Village and close to the town center ...
From $220 per night (USD)VRBO
- Click For Pricing
VRBO
Cozy getaway in Litchfield County - Pet Friendly!\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our enchanting Cottage at the Grove! Whether you seek relaxation, outdoor adventures, or a cozy retreat, our ...
Click For PricingVRBO
- From $75 per night (USD)
Expedia
Cozy cottage with kettle pond lake 2 minutes away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
You'll be staying in a cottage located on the backside of a larger old family home property. There is one tenant in the ...
From $75 per night (USD)Expedia
- From $119 per night (USD)
VRBO
#31 - Downtown Terryville- 1 Br
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to our beautifully renovated 1-Bedroom Apartment nestled in the heart of Terryville, a charming town in ...
From $119 per night (USD)VRBO
- From $126 per night (USD)
VRBO
Charming apartment minutes from downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming, comfy entire 1st floor apartment. Recently renovated from the studs on up. Exceptionally clean. Just minutes f ...
From $126 per night (USD)VRBO
- From $200 per night (USD)
VRBO
The Blue Elm - A Historic Berkshire Cottage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA. Set on 3.5 tranquil acres, ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Litchfield County Farmhouse with a Modern Twist\n\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mi ...
Click For PricingExpedia
- From $525 per night (USD)
VRBO
Bantam Beauty - Surrounded by nature! APRIL & MAY SPECIAL OFFER!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
SPECIAL OFFER FOR APRIL & MAY STAYS. BOOK 2 NIGHTS, GET A 3rd NIGHT FREE! (For Memorial Day Weekend, book 3 nights, get ...
From $525 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Jim & Pat’s Litchfield Hills Hideaway on 3.0 acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location, Location , Location .Transport yourself into our private Hideaway , a quiet three bedroom home on 3+ acres at ...
From $327 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Jim & Pat’s Litchfield Hills Lookout on 4.3 acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location, Location, Location......with sweeping distant views towards Mt. Tom and the Litchfield Hills the Lookout offer ...
From $325 per night (USD)VRBO
- From $708 per night (USD)
Expedia
Litchfield County Historic Estate: 10 Acres + Pool
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 11
Ninety-five miles from New York City and worlds away, discover this gorgeous 6-bedroom country home, with 5 full baths a ...
From $708 per night (USD)Expedia
- From $210 per night (USD)
VRBO
Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our lovely 1810 cottage, on a quiet road is bright, cozy, and comfortable. We have two bedrooms, with artwork and books, ...
From $210 per night (USD)VRBO
- Click For Pricing
VRBO
Private Woodland Sanctuary—8 mins to a Ski Sundown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax in this calm, stylish space with your loved ones and furbabies in New Hartford, CT. Indulge in the p ...
Click For PricingVRBO
- From $632 per night (USD)
VRBO
Lakefront Lakehouse Luxury in Connecticut
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Lakefront modern clean home with amazing lake views throughout the entire home. Full kitchen with Nespresso coffee and ...
From $632 per night (USD)VRBO
- From $259 per night (USD)
VRBO
Quiet Historic Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Step back in time and experience the charm of a colonial cottage with a history as rich as the rolling hills of Litchfie ...
From $259 per night (USD)VRBO
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VRBO
Harwinton Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our charming cottage, nestled amidst mature gardens on a sprawling property, offers an idyllic escape for those seeking ...
Click For PricingVRBO
- From $200 per night (USD)
Expedia
Charming and Relaxing 4br Farmhouse - Ski + Hiking\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on ...
From $200 per night (USD)Expedia
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VRBO
Luxury condo at beautiful community lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful condo on the begging of new milford 5min from the high away, 5 min from the lake if the weather he nice I have ...
Click For PricingVRBO
- From $356 per night (USD)
Expedia
Country home vacation oasis with pool, hot tub, near lake\/hiking.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax by the pool during the day, hot tub and fire-pit at night. Outdoor cooking on grill, griddle and pizza oven. Spraw ...
From $356 per night (USD)Expedia
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Expedia
BANTAM GEM: 5 ACRES, LAKE VIEW, HEATED POOL, BBQ, GYM, LAWN, GREAT ZEN ESCAPE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream rental property nestled in the picturesque hills of Litchfield, CT. This cozy and peaceful home bo ...
Click For PricingExpedia
- From $384 per night (USD)
Expedia
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Charming and spectacular colonial in every single detail. Modern and rustic interior at the same time. Enjoy the comfort ...
From $384 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
Charming Country House with Pool, Spa, and Garden
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the hills of Litchfield County, this charming country house is surrounded by 2.5 acres for lots of privacy, y ...
From $2000 per night (USD)VRBO
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Expedia
Tranquil\/Comtemporary\/Pool\/Privacy
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
sunny contemporary retreat! This elegant 3-bedroom house with a fully finished basement and two-car garage offers comple ...
Click For PricingExpedia
- From $392 per night (USD)
VRBO
Private home next to Candlewood lake and Candle Light farms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Candlewood Corners Retreat, your spacious 3 bedroom, 2.5 bath getaway nestled in the heart of nature's beauty ...
From $392 per night (USD)VRBO
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Expedia
Moody Pond House: 15 Min to Mohawk Ski Mountain, new country home on 18+ acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand new family friendly modern home with in-ground gunite pool set on 18.5 acres with a large pond. 5 minute drive fro ...
Click For PricingExpedia
- From $274 per night (USD)
VRBO
Farm House
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
A serene get away in a guest house on a real working farm. We homesteaded this property in 2012 and have created our own ...
From $274 per night (USD)VRBO
- From $456 per night (USD)
VRBO
Music Mtn Farmhouse - Mystical Country Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover Music Mountain Farmhouse, a beautifully renovated farmhouse that exudes timeless charm and design with ...
From $456 per night (USD)VRBO
- Click For Pricing
VRBO
Charming renovated farmhouse with hot-tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Charming, beautifully renovated farmhouse perfect for ski visits, spring hikes and summer lakes. 10 mins to Mohawk ski. ...
Click For PricingVRBO
- Click For Pricing
Expedia
Riverside Paradise in Litchfield
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 6
Forget your worries in this fully renovated, light-filled and serene space in the heart of the rolling hills of Litchfie ...
Click For PricingExpedia
- From $653 per night (USD)
VRBO
Direct Waterfront on Candlewood Lake, 2 Private Docks, 5 Bedrooms, Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful direct western exposure on Candlewood Lake's quiet north eastern section. The property has a large lake-side ...
From $653 per night (USD)VRBO
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Expedia
Vibrant, secluded dome home in Litchfield County!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Positive vibes, tranquility and refuge await! Reconnect with nature at this unforgettable escape on 3+ acres. Allowing a ...
Click For PricingExpedia
- From $200 per night (USD)
VRBO
Modern Terryville Cottage w\/ Deck & Lake View!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience a peaceful retreat by the lake at this modern Terryville vacation rental! Complete with 2 bedrooms, a luxury ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Luxurious Country Colonial in Roxbury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy country colonial sits on a quiet road in idyllic Roxbury. The stylish residence has just been gut renovated to ...
Click For PricingExpedia