Litchfield Area Rentals
From $426 per night (USD)VRBO
Lakefront Spring Stunner in New England Just 2 Hours From NYC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Inside Our Cabin (Central Air and Heat) We have a brand new kitchen with a stainless steel dishwasher, fridge and range ...
From $426 per night (USD)VRBO
From $333 per night (USD)Expedia
In town, walk to everything, close to Kent, South Kent and Marvelwood schools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the heart of the village, this private get-away awaits you. Relax and still be in the center of everything. ...
From $333 per night (USD)Expedia
From $614 per night (USD)VRBO
Antique Farmhouse Totally Restored
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a ho ...
From $614 per night (USD)VRBO
From $336 per night (USD)Expedia
Charming 1870 cape cottage in Litchfield
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
A beautifully renovated cottage just minutes away from Bantam and Litchfield, this is the perfect getaway for a couple o ...
From $336 per night (USD)Expedia
From $263 per night (USD)VRBO
Two Bedroom Cottage Close To Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charmingly updated two bedroom home has a wonderful open floor plan. The living room is bright and spacious and has a wo ...
From $263 per night (USD)VRBO
From $920 per night (USD)Expedia
Modern Barn, NEW Luxurious Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
The contemporary Barn welcomes guests as a luxury getaway and gorgeous views of rolling hills & sunsets over Washington, ...
From $920 per night (USD)Expedia
From $376 per night (USD)VRBO
The Perfect Escape From The City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perched on a rise in the beautiful lower Berkshires of Litchfield County, this house is your ideal escape from city life ...
From $376 per night (USD)VRBO
From $204 per night (USD)Expedia
Quaint cottage located directly on Long Meadow Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Wonderful lakefront cottage with a sun porch, sunny deck, 2 bedrooms, 1 bathroom, beautiful sunsets, and your own privat ...
From $204 per night (USD)Expedia
From $210 per night (USD)VRBO
Guest Cottage on Country Estate
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our 2 bedroom guest house in the center of Watertown! The property sits on a 7 acre estate designed by Olmst ...
From $210 per night (USD)VRBO
From $2519 per night (USD)Expedia
Nature & Luxury @Lavender Lake Est (Kosher optional)
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 20
Dream country home!! We recently purchased the ‘Lavender Lake Estate’ after a multi-year search for the perfect country ...
From $2519 per night (USD)Expedia
From $1766 per night (USD)VRBO
Candlewood Lake - Amazing Views, Waterfront & Water Access
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Newly-renovated house on Candlewood Lake, 1.5 hrs from NYC. Amazing views of the lake, complete privacy, waterfront, acc ...
From $1766 per night (USD)VRBO
From $1057 per night (USD)Expedia
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT \"TOPHET POOL BARN\" Ski,Pool,BBQ,Magical!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spectacular Vaulted Beamed Ceiling Pool Barn with King Bed and Sleeper Sofa Rec Room & Office Area. Salt water heated p ...
From $1057 per night (USD)Expedia
From $1099 per night (USD)VRBO
BEST TOWN ROXBURY! PoshPadsCT\"TOPHET 3BR\"Ski,Heated Winter Pool\/Spa,Bikes,GasBBQ
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land ...
From $1099 per night (USD)VRBO
From $302 per night (USD)Expedia
Secluded Cabin for the Perfect Weekend Escape
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Relax in our quiet, quaint & super cute cottage in Northwest Connecticut. Just 2 hours from NYC. Spend your days antiqui ...
From $302 per night (USD)Expedia
From $270 per night (USD)VRBO
Family-Friendly Woodbury Home with Yard + Deck!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
Look no further than this serene Woodbury vacation rental for your next family getaway! With 3 bedrooms, 1.5 baths, 2 li ...
From $270 per night (USD)VRBO
From $323 per night (USD)Expedia
Private Kent Getaway With Views, Pond & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Close to the charming town of Kent, yet secluded on 9 acres, this cozy house provides all-season access to New England a ...
From $323 per night (USD)Expedia
From $1155 per night (USD)VRBO
BEST LOCATION! PoshPadsCT\"PAINTER HILL4BR\" Hot Tub Spa, BBQ, Ski,Hike,1.5HrsNYC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Roxbury & Washington are the best country rural retreats within 2 hours of NYC - the best restaurants, shopping, land pr ...
From $1155 per night (USD)VRBO
From $373 per night (USD)Expedia
SPRING 2025! Cozy WATERFRONT Cottage on Highland Lake, CT - central a\/c & heat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our cottage on Highland Lake, a 445-acre lake located in the rolling hills of Northwestern Connecticut. Thi ...
From $373 per night (USD)Expedia
From $1359 per night (USD)VRBO
Best Town WASHINGTON! PoshPadsCT\"51 SENFF\" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1359 per night (USD)VRBO
From $608 per night (USD)Expedia
Check Out One of the Original Summer Cottages on Lake Warmaug
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
New Expanded Deck for great outside living. Propane BBQ. Lots of seating for lazy afternoons or morning coffee. CUR ...
From $608 per night (USD)Expedia
From $518 per night (USD)VRBO
Charming country home in Roxbury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Charming country retreat located in the beautiful northwest corner of the Litchfield hills in bucolic Roxbury, CT. Roxb ...
From $518 per night (USD)VRBO
From $1404 per night (USD)Expedia
100% ROXBURY! PoshPadsCT \"MOOSEHORN\" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land ...
From $1404 per night (USD)Expedia
From $706 per night (USD)VRBO
Luxurious Mountain Retreat - Private 40-Acre Family Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy total privacy at this cozy mountain home on 40 acres, just minutes from ski resorts and charming shops. With floo ...
From $706 per night (USD)VRBO
From $570 per night (USD)Expedia
Cozy Lakefront Bungalow w firepit\/dock\/kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a lakefront getaway at Bungalow Bliss. Experience idyllic lakefront living and expansive views from the many uniqu ...
From $570 per night (USD)Expedia
From $1134 per night (USD)VRBO
BEST TOWN! PoshPadsCT \"TUNNEL\" Ski!, 4-BR SPA-POOL, Bike, Hiking, NYC 1.5 Hrs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Roxbury & Washington are the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land pre ...
From $1134 per night (USD)VRBO
From $199 per night (USD)Expedia
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the Beauty of Roxbury, Connecticut Unwind in the hills at this peaceful and private loft nestled above a barn ...
From $199 per night (USD)Expedia
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Spacious country home minutes from Litchfield Green and downtown Torrington
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Spacious hilltop country home with terraces overlooking spacious lawn and gardens located a few minutes between the tow ...
Click For PricingVRBO
From $539 per night (USD)Expedia
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Come stay for sunset hour and enjoy dramatic views from the comfort of the living room, kitchen, or outdoor patio. This ...
From $539 per night (USD)Expedia
Click For PricingVRBO
Candlewood Lake Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property shares a unique waterfront with one other tenant. This rental is a studio apartment with a kitchen, bathr ...
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From $546 per night (USD)Expedia
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Looking for a vacation home? This beautiful home was built in 2009 on Highland Lake, a 444-acre lake nestled in the Ber ...
From $546 per night (USD)Expedia
From $581 per night (USD)VRBO
Serene Lake House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This serene and private 4 bedroom home overlooks a private pond and sweeping grounds. Tucked away on 5 acres of private ...
From $581 per night (USD)VRBO
From $749 per night (USD)Expedia
Hilltop House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled just outside the center of Bantam, this immaculate 3 bedroom 2.5 bath home with a pool is the ultimate retreat. ...
From $749 per night (USD)Expedia
From $1071 per night (USD)VRBO
The Lake House on Lake Waramaug
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Indulge in a serene escape with a stay at a charming lake house nestled on the tranquil shores of Lake Waramaug. This in ...
From $1071 per night (USD)VRBO
From $178 per night (USD)Expedia
River tubes, electric bikes, kayaks, skiing, more \n2 minutes to the river
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Entire apartment in a side by side duplex. Just 5 minutes from Ski Sundown. 2 minutes to Farmington River. 3 bedrooms wi ...
From $178 per night (USD)Expedia
Click For PricingVRBO
Idillic summer getaway in Litchfield Hills, CT.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A converted horse barn, this quintessential CT Highlands country home provides the perfect place to enjoy the area's wid ...
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From $1303 per night (USD)Expedia
BEST TOWN WASHINGTON! \"Kielwasser\" PoshPadsCT Ski, Pool, 4 FPs, Bikes, Orchards
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1303 per night (USD)Expedia
From $1405 per night (USD)VRBO
Large family compound , guest house, barn, pool on 13 acres
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 0
Charming antique CT farmhouse with outbuildings. It is the perfect place for large active families and reunions. The mai ...
From $1405 per night (USD)VRBO
From $532 per night (USD)Expedia
Gorgeous Luxury Farmhouse in the Hudson Valley New York
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Light, bright and airy, this immaculate new farm home boasts 2 bedrooms and 2.5 baths. Nestled into rolling hills of Ups ...
From $532 per night (USD)Expedia
From $613 per night (USD)VRBO
Quintessential Connecticut Living 5BRD\/3 bath Home with Game Room and Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Quiet 5 Air Conditioned* bedroom house in the Connecticut Countryside close to everything, but far away from the hustle ...
From $613 per night (USD)VRBO
From $2067 per night (USD)Expedia
Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Stunning and exceptionally private log cabin retreat located in the center of 62 Acres of wooded land. The driveway is a ...
From $2067 per night (USD)Expedia
From $288 per night (USD)VRBO
Great Family Cabin in the woods on a lake.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
In the woods and on a lake, Wood burning stove for heat, galley Kitchen, Gas grill, canoes and kayaks. Swim right off o ...
From $288 per night (USD)VRBO
From $235 per night (USD)Expedia
Charming 3BR Hilltop House, Newly Remodeled with Arcade
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
WOW! The Lindan Hill House is a perfect VRBO balance of luxury and value! Stay and play as you enjoy our 5 Star remodele ...
From $235 per night (USD)Expedia
From $393 per night (USD)VRBO
Perfect cabin getaway. 5mins from hiking trails & lake Waramaug
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect getaway cabin. Our 3 bedroom is great for couples, families or a group of friends. Newly renovated and has ...
From $393 per night (USD)VRBO
Click For PricingExpedia
NEW! Charming Lakefront House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
It's summertime and relaxing is easy...at the LAKE! Charming lake house with dock, fishing, swimming, kayaking, paddle b ...
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Click For PricingVRBO
Bring the family, work from home in this Historic 5 Bdrm house in Litchfield
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to the Tavern! This grand c.1781 home features 7 fireplaces, 5 bedrooms, an office, 2 sitting rooms, dining room ...
Click For PricingVRBO
From $939 per night (USD)Expedia
Experience Perch Rocks! A Unique Private Waterfront Cottage on Bantam Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Perch Rocks is a luxury camp on Bantam Lake in Litchfield County! This is a true 'lake cottage' with classic shingle st ...
From $939 per night (USD)Expedia
From $768 per night (USD)VRBO
6-Acre Luxurious Country Home with Goddess Point Lookout
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Set atop a beautiful lookout, this exquisite Woodbury home warmly welcomes you for your next vacation stay. The perfect ...
From $768 per night (USD)VRBO
From $1465 per night (USD)Expedia
WARREN-NYC 2Hrs, Ski Mohawk!, 5BR Mint Design, Pool, Tennis, 20 Acres PoshPadsCT
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Private Mint 5-Bedroom, 4-Bath Country Estate in one of Warren's Best walking, bike riding locations surrounded by large ...
From $1465 per night (USD)Expedia
From $713 per night (USD)VRBO
Beautiful New Milford home(1\/4mile to Candlewood Lake & Marina+big private pool)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful vacation home fully updated in 2021 with brand new furniture throughout (1/4 mile to Candlewood Lake and local ...
From $713 per night (USD)VRBO
From $511 per night (USD)Expedia
Fickle Fox Farm. Daffodils are popping their heads up, summer is coming!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Newly renovated three bedroom, two and half bath home on 6 bucolic acres in Canaan Valley, CT. Spend lazy summer days i ...
From $511 per night (USD)Expedia
From $561 per night (USD)VRBO
Lakeview Cottage with Dock, Kayaks
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This newly renovated, cozy cottage on pristine Bantam Lake is super-relaxing and perfect for kids of all ages. Guests ha ...
From $561 per night (USD)VRBO
From $272 per night (USD)Expedia
Barn Apartment Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Second level apartment of barn/garage on beautifully renovated antique farmhouse property less than a mile from the quai ...
From $272 per night (USD)Expedia
From $678 per night (USD)VRBO
Curated Contemporary for lakes, forest & ski hills
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this calm, stylish home, nestled in the foothills of Mt. Washington State Forest on the Mass-CT border. The hom ...
From $678 per night (USD)VRBO
Click For PricingExpedia
Tranquil Farmhouse Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You can enjoy our relaxing and tranquil property while enjoying the jacuzzi! Our apartment affords Fully Independent Li ...
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From $192 per night (USD)VRBO
Charming, river front compound
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront terraces, Large living room with propane fireplace and french doors to river. Large dining room, with firepl ...
From $192 per night (USD)VRBO
Click For PricingExpedia
Scenic Country Local Antique Hiking rafting
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Country local residence 2 beds kitchen large bath living and dining room. Paradise for those who enjoy antiqing, hiking ...
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From $1932 per night (USD)VRBO
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions \/ groups
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 18
On two acres, our stunning lakefront retreat is perfect for group gatherings, corporate retreats, and family reunions. ...
From $1932 per night (USD)VRBO
From $326 per night (USD)Expedia
The Goshen Glass Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A beautiful vacation house renovated. New modern furnished decorated 1 large master bedroom 1 full size bed & 2 twin siz ...
From $326 per night (USD)Expedia
From $808 per night (USD)VRBO
The Country Retreat House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Immerse yourself in country living from the heart of the Litchfield Hills. The space This 13-acre Riverfront oasis mean ...
From $808 per night (USD)VRBO
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Lakefront Tranquility\/Fishermans Delight
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a stay at our cozy, 2 bedroom cottage on West Hill Lake in New Hartford. Situated on the south shore, the view f ...
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From $366 per night (USD)VRBO
2023-2024 Academic Listing Connecticut Farm House With Breathtaking Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Monthly rental for the 2023-2024 academic calendar from September 6, 2023 through the May 31, 2024. Fully renovated 191 ...
From $366 per night (USD)VRBO
From $591 per night (USD)Expedia
6 BR 'CAMP' House on Twin Lakes - Epic Historic Property
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
The perfect home for your big group or family, with a charming history! This beautiful, spacious vacation home was forme ...
From $591 per night (USD)Expedia
From $318 per night (USD)VRBO
Rustic escape on a pond with 7 acres in Colebrook, CT!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Quarantine in a rustic cottage in Colebrook, Ct in beautiful Litchfield County...less than mile to Mass. border and Camp ...
From $318 per night (USD)VRBO
From $359 per night (USD)Expedia
Waterfront modern cottage. Great getaway- summer retreat under 2 hours from NYC!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This sun-filled, modern home is directly on Long Meadow Pond, a lovely, quiet freshwater lake. Enjoy beautiful views all ...
From $359 per night (USD)Expedia
From $1168 per night (USD)VRBO
Expansive, Five Bedroom House with Pool. Ideal for Multiple Family Travel
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Expansive 4.5 bed, 4.5 bathroom cape centrally located on a quiet street, one mile from the Mayflower Inn & Spa. House ...
From $1168 per night (USD)VRBO
From $460 per night (USD)Expedia
5 min walk to private beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Longview Lakehouse! We are located in a private lake community on Candlewood Lake in Brookfield, CT. Access t ...
From $460 per night (USD)Expedia
From $424 per night (USD)VRBO
Ashley Falls Home w\/ Fire Pit: Hike & Ski!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Game Room | 2,734 Sq Ft | ~6 Mi to Campbell Falls State Park Whether you’re chasing waterfalls in the summer, leaf-peep ...
From $424 per night (USD)VRBO
From $277 per night (USD)Expedia
Private Annex\/Former Artist Studio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and dream of your life as an artist! This beautiful retreat was once an artist's studio and Marc Chagall's respit ...
From $277 per night (USD)Expedia
From $1195 per night (USD)VRBO
BEST TOWN ROXBURY! PoshPadsCT \"PAINTER - POOL\" 1.5Hrs NYC, Mint, Ski, Fires, BBQ
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Roxbury & Washington are the best country rural retreats within 2 hours of NYC - the best restaurants, shopping, land pr ...
From $1195 per night (USD)VRBO
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Idyllic escape private home with heated pool and hot tub
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Secluded but conveniently located near New Milford and Bridgewater, this idyllic 10+ room retreat is spread over 3 level ...
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From $503 per night (USD)VRBO
Mountain View Farmhouse, pool\/hot tub, fire pit, 4 seasons porch, game room
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the Irondale Manor, an 1870s farmhouse with modern touches. While only half a mile from Millerton's Main St, ...
From $503 per night (USD)VRBO
From $1447 per night (USD)Expedia
Beautiful Farmhouse on 14 Acres
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Originally built in 1790, this farmhouse is the perfect mix of old world charm and modern convenience. Nestled just outs ...
From $1447 per night (USD)Expedia
From $370 per night (USD)VRBO
Mountain View Getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy this private oasis at the summit of Cream Hill nestled in picturesque Northwest CT. This property, at the end of a ...
From $370 per night (USD)VRBO
From $368 per night (USD)Expedia
The Inn at Knife Shop Falls - A Historic Waterfront Getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Calling all history buffs and nature lovers! Relax and recharge in this beautiful WATERFRONT 190-year-old piece of Conne ...
From $368 per night (USD)Expedia
From $526 per night (USD)VRBO
Exclusive & Bucolic Spot in Ideal Area with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Magical retreat in exclusive location of multi-million dollar homes. Listen to the rushing river from every room. Heated ...
From $526 per night (USD)VRBO
From $302 per night (USD)Expedia
The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly Renovated Barn, 2 floors of scenic marsh views. 3 minutes from Millerton, lakes and Hotchkiss. Open loft, Queen Be ...
From $302 per night (USD)Expedia
From $282 per night (USD)VRBO
Newly Renovated 18th Century Cottage On 4 Acres
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Original exposed beams, cozy furniture, spacious screened in porch with seating area, grill, outdoor space with fire pit ...
From $282 per night (USD)VRBO
From $1909 per night (USD)Expedia
100% WASHINGTON! PoshPadsCT \"SUNNY RIDGE\" 8-BR Estate, Heated Pool, BBQ, Magical
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
Sunny Ridge Farm is a magnificent country estate on 14 acres in the Sunny Ridge Historic District. It is the largest ho ...
From $1909 per night (USD)Expedia
From $546 per night (USD)VRBO
Summer Lake Cottage, private beach, Berkshire Hills, small village
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 18
This is the lake cottage your grandmother visited during her childhood. Charming, original 1920 features. Big remodeled ...
From $546 per night (USD)VRBO
From $230 per night (USD)Expedia
Stay on an Alpaca Farm
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Live on a working Alpaca Farm! Enjoy the peace and beauty of these lovely animals. We are on 50 acres with plenty of roo ...
From $230 per night (USD)Expedia
From $366 per night (USD)VRBO
Spacious Home nestled along the Blackberry River in Northwest CT
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This beautiful house is on 3 acres to enjoy. 3 bedroom, 3 bathroom. 1 king ,1 queen, 1 full 2 twins , queen futon and do ...
From $366 per night (USD)VRBO
From $600 per night (USD)Expedia
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Our farmhouse was built in 1793 and renovated early in the 21st century. It offers all the modern amenities, but in a hi ...
From $600 per night (USD)Expedia
From $244 per night (USD)VRBO
Charming 1760 Cape Nestled in the Foothills of Litchfield County
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Located in Woodbury CT, a small picturesque New England town known for its antiques, farm to table restaurants and sceni ...
From $244 per night (USD)VRBO
From $103 per night (USD)Expedia
Small Town Stay- Stroll to Local Shops\/Dining\/Taft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This getaway is small enough to feel cozy, yet with amenities you want. What’s more is its convenient location to main s ...
From $103 per night (USD)Expedia
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Waterbury Home: Playground & Porch Swing
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
Looking to relax in a homey environment? Then this 4-bedroom, 1.5-bathroom vacation rental is just the place for you and ...
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From $156 per night (USD)Expedia
Very charming house , that will make you feel like home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
1 fireplace we have to make you feel cozy .A center kitchen that I guess can cook .the house is located in the heart of ...
From $156 per night (USD)Expedia
From $755 per night (USD)VRBO
Spectacular Cottage at Bantam Lake, Sleeps 12
- Bedrooms:
- 1
- Bathrooms:
- 7
- Sleeps:
- 12
This 7-bedroom cottage overlooks pristine Bantam Lake, with dock and kayaks. Cottage features 2 stories -- 3 bedrooms on ...
From $755 per night (USD)VRBO
From $430 per night (USD)Expedia
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home sits right on the front straightaway of Lime Rock Park , yes you can see the cars from this property, Home has ...
From $430 per night (USD)Expedia
From $271 per night (USD)VRBO
Modern Escape w\/ Fire Pit, Near Lake Waramaug
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to immerse yourself in all that this newly renovated 2-bedroom, 1-bath guest home has to offer! This sleek vac ...
From $271 per night (USD)VRBO
Click For PricingExpedia
Cheerful Stunning 3 bed 4 bath Villa in a Mansion with Pool 30
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Forget your worries in this spacious and serene space. Comfort, quiet and relaxation so close to home is just what the d ...
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Click For PricingVRBO
Mid Century Modern Mountain Retreat Bordered by Preserve
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 6
A nature oasis a small mountain in the Litchfield Hills of Connecticut. Near renowned bike and hike trails as well as p ...
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From $530 per night (USD)Expedia
BEAUTIFUL TWIN LAKES RENTAL - Weekly or Seasonal Term Available
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
So much more than just a beautiful house on a lake!! This is a beautiful cottage situated on an epic property directly o ...
From $530 per night (USD)Expedia
From $210 per night (USD)VRBO
Within a walking distance of hiking trails and a short drive to Lake Waramaug.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This artist's home in the woods allows one to get in touch with their natural side. Featured in Connecticut Cottages and ...
From $210 per night (USD)VRBO
From $373 per night (USD)Expedia
Charming Cottage in Washington Depot
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming rural cabin in beautiful Washington Depot, Connecticut. This property is situated high on a hill above the roa ...
From $373 per night (USD)Expedia
From $588 per night (USD)VRBO
Classic Roxbury Home w\/ Picturesque Backyard!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
Designed with enhanced classic finishes, charming architecture, and an updated interior, this 3-bedroom, 2.5-bathroom va ...
From $588 per night (USD)VRBO
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Quiet, sweet house in the heart of Litchfield\/the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A quiet, 1 level house, with 2 bedrooms, 2 living rooms, a small outdoor deck. Near the towns of Lakeville & Salisbury. ...
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From $1290 per night (USD)VRBO
Fabulous year round waterfront retreat on Lake Waramaug
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come unwind & enjoy all that New Preston has to offer in our brand new house on Lake Waramaug. Our cozy, yet bright and ...
From $1290 per night (USD)VRBO
From $1396 per night (USD)Expedia
Immaculate waterfront home nestled in the Litchfield hills w\/ tons of...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
The Stillwater Immaculate waterfront home nestled in the Litchfield hills w/ tons of amenities and a private sandy beac ...
From $1396 per night (USD)Expedia
From $1351 per night (USD)VRBO
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy year-round activities at this authentic 5,100 SQ FT Swiss Chalet with 220v Tesla charger and Super Internet 1.1 Gb ...
From $1351 per night (USD)VRBO
From $518 per night (USD)VRBO
Close to Lime Rock, Prep Schools, 3 Ski Areas
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Kellogg Haus located in Falls Village, CT, near 3 ski areas and Lime Rock Park for the car enthusiast. Enjoy ...
From $518 per night (USD)VRBO