Litchfield Area Rentals
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VRBO
Club Getaway Pine Grove 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
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Expedia
Club Getaway Pine Grove 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingExpedia
- From $656 per night (USD)
VRBO
Fall & Winter @ chic restored barn. Summer '24 w pool.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy all seasons in this lovely and oh-so-comfy home in rural Litchfield County. The Barn on Looking Glass Hill has a ...
From $656 per night (USD)VRBO
- From $358 per night (USD)
VRBO
County Seat Colonial
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your home away from home: come relax and enjoy all Litchfield has to offer. The home is located in the heart of the Litc ...
From $358 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Captivating Artisan Built Home With Spectacular Water Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Geno ...
From $225 per night (USD)VRBO
- From $314 per night (USD)
Expedia
Newly Renovated Family House On Highland Lake with Dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
This family estate is set privately on a full acre with beautiful views of Highland Lake. Red Barn Brewing and main str ...
From $314 per night (USD)Expedia
- From $217 per night (USD)
VRBO
Beautiful Cottage and Waterfront Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy classic New England weekends and holidays year-round on Lake Waramaug’s Gold Coast. Waramaug is a Connecticut Her ...
From $217 per night (USD)VRBO
- From $166 per night (USD)
VRBO
Lake Waramaug Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
RATES: 233 per night Digital Detox! Close your screens and experience life again in real time. An immaculate, ...
From $166 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Spacious family home with open floor plan…and close to the lake!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Woodridge Retreat! A spacious, pet-free family home...residing on over an acre of wooded land...in a pea ...
From $341 per night (USD)VRBO
- From $590 per night (USD)
VRBO
An acclaimed photographers country estate, arts community, near private schools!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This Federal Style home has many original details, a center hall with an arched entrance and a spiral staircase going up ...
From $590 per night (USD)VRBO
- From $1250 per night (USD)
VRBO
Beautiful Country Estate with Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Tullymargy - Beautiful Country Estate Very Private, 4 Bedrooms, 3.5 baths, 12 rooms, Heated, Saltwater Pool, In-pool Spa ...
From $1250 per night (USD)VRBO
- From $342 per night (USD)
VRBO
Cozy in the hills of Cape Litchfield
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where ...
From $342 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Country Living at its best in this Sharon Estate with indoor pool*
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful and private estate home with all amenities, 3 bedrooms, 5 baths in Sharon CT on Horse Estate property with att ...
From $600 per night (USD)VRBO
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Expedia
Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT .
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The good about this house is it on dead end quite street in Torrington CT, beautiful four bedrooms single family home w ...
Click For PricingExpedia
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VRBO
Modern Country Compound w\/ guest cottage, pool & sauna! ca. 1790
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 14
Cross the private bridge to enter an oasis of quiet and calm...formerly Isaac Stern's country estate, this inviting retr ...
Click For PricingVRBO
- From $117 per night (USD)
Expedia
Fantastic Cape in Historic Litchfield
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful fully renovated cape just minutes from the village of Litchfield. Beautiful kitchen and Living room, huge out ...
From $117 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
My clean and sanitized home is available for longer stays. Please contact me for more details. My home has all the ameni ...
From $275 per night (USD)VRBO
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Expedia
Club Getaway Valley View 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
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VRBO
Club Getaway Mountain View 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
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Expedia
Club Getaway Pine Grove 1
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingExpedia
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VRBO
Club Getaway Valley View 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
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Expedia
Club Getaway Lake View 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingExpedia
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VRBO
Club Getaway Mountain View 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingVRBO
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Expedia
Club Getaway Mountain View 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingExpedia
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VRBO
Club Getaway Valley View 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingVRBO
- From $438 per night (USD)
VRBO
Amazing Lake House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Best view of the lake! This home has gone through a major make-over and has been transformed to a place you aren’t goin ...
From $438 per night (USD)VRBO
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VRBO
Club Getaway Lake View 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to be socially distant in the beautiful Berkshire Mountains? Club Getaway is a resort in the heart of Kent CT, Surr ...
Click For PricingVRBO
- From $864 per night (USD)
VRBO
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A modern and comfortable home nestled in the woods in a vibrant and interesting area. Great for athletes, cooks and gett ...
From $864 per night (USD)VRBO
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Expedia
Beautiful Highland lake in Connecticut
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautiful lake in Connecticut.House is across the street. It has a lake view. Very easy access into the lake. Paddle boa ...
Click For PricingExpedia
- From $260 per night (USD)
Expedia
Charming Sharon Dwelling w\/ Deck & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on the New York-Connecticut border outside of Sharon, this lovely home offers the perfect space for your next fa ...
From $260 per night (USD)Expedia
- From $480 per night (USD)
VRBO
Heavenly summer getaway in Litchfield Hills, CT.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A charming country home in historic equestrian estate, this former caretaker house comfortably fits 4 adults in 2 BRS, 2 ...
From $480 per night (USD)VRBO
- From $284 per night (USD)
VRBO
Pristine Private Lakefront Cottage in West Hartland CT - Two Season Rentals
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Now booking for the months of May-August, to quiet, low key family/friend groups as well as couples. Booking is for 6 n ...
From $284 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Direct Waterfront with Private Beach - Entire Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newer Listing! Enjoy direct waterfront living on one of the cleanest and tranquil lakes in the state. This fully furnish ...
From $314 per night (USD)VRBO
- From $462 per night (USD)
VRBO
Long Meadow Manor, heated pool, 5 min from U-pick farm and Lake
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled in the Litchfield Hills of Connecticut on 1.6 acres and backing up to beautiful woods is Long Meadow Manor. Near ...
From $462 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Private Country Retreat in Lovely Lakeville CT
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
RECENTLY RENOVATED! Our vacation home in Lakeville is the perfect retreat for several couples or a large family to escap ...
From $450 per night (USD)VRBO
- From $285 per night (USD)
VRBO
Historic Warren\/Kent Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This wonderful home is available for a ski getaway or a spring or summer get together. A historic 1755, home with trem ...
From $285 per night (USD)VRBO
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VRBO
BEAUTIFUL APARTMENT WITH SCENIC VIEWS
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come home to a warm and cozy apartment In historic downtown Torrington. Breathtaking views of mountains with many outdo ...
Click For PricingVRBO
- From $1400 per night (USD)
Expedia
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
There are many great homes you can rent but if the weather turns are there enough things to do to occupy your guests? H ...
From $1400 per night (USD)Expedia
- From $459 per night (USD)
VRBO
Twilight Dreams Farm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A rustic 250 year old working farm abutting one of the best trail systems in Roxbury. Home to several horses, a large f ...
From $459 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Lakeridge Litchfield Resort Townhome Pool Tennis Skiing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
****Note: 30-day minimum rental, no exceptions**** We are offering for rent a spacious 2 bedroom, sun-lit, 2-story, all- ...
From $120 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Make lifelong memories at this New England Quintessential Country Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful 1905 New England Cottage, that was once a local bakery, is the perfect location to enjoy Connecticut, fun ...
From $330 per night (USD)VRBO
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Expedia
Summer Cottage - Bike to Lake Waramaug
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A wonderful arts and crafts cottage with the perfect porch to sit or dine on ....wicker chairs and dining table enable y ...
Click For PricingExpedia
- From $278 per night (USD)
VRBO
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a lovely classic New England vacation in this lake front,open concept, home on Harwinton Lake. Relax and enjoy the ...
From $278 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Indoor Pool, Sauna, Hot Tub, Jacuzzi & Solarium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Prana Residence-Spa is a holistically designed residence provides total relaxation and the transformation of vital life ...
From $750 per night (USD)VRBO
- From $266 per night (USD)
VRBO
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
If you love to cook our totally redone cottage has a gourmet kitchen, complete with double oven and full spice rack alon ...
From $266 per night (USD)VRBO
- From $680 per night (USD)
VRBO
Direct Water Front Home, Private Boat Dock, Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully furnished direct waterfront single family home with Westerly views. 3 bedrooms, 2 full bathrooms, and living room ...
From $680 per night (USD)VRBO
- From $350 per night (USD)
VRBO
1770 Colonial 5 Bedrooms 4 1\/2 Baths Sleeps 9
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
This former tavern retains a lot of colonial-era charm and is a beautiful and peaceful place to stay. It remains a great ...
From $350 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
RATE NOTE: Email for reduced on rate for off-season visits for more than 6 nights (November through April) . Antique ...
From $225 per night (USD)VRBO
- From $90 per night (USD)
VRBO
The Beehive Cottage in Cornwall Bridge MONTHLY RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming, Rustic, Casual Summer Home set in the middle of a nature preserve. This cottage is not fancy, but fully furnis ...
From $90 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy a relaxing getaway at the lake. Sip your morning coffee on the deck overlooking the lake; swim from your private b ...
From $375 per night (USD)Expedia
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VRBO
Spectacular Silo House on Litchfield Hills Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully refinished Silo house on pristine Litchfield Hills estate! The house features antique furnishings and great ...
Click For PricingVRBO
- From $496 per night (USD)
VRBO
A Haven in the Country-
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Sprawling country home located in historic Washington, CT. 90 minutes from New York City and Boston, Litchfield County ...
From $496 per night (USD)VRBO
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VRBO
Hidden Quarry Country Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
The Hidden Quarry Country Home is quietly tucked between the Shepaug River and 30 shared acres for CT forest. Swedish s ...
Click For PricingVRBO
- From $495 per night (USD)
VRBO
Pet & Kid Friendly, Solar, 13 Acres, Saltwater Pool, River Views, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
3 bedrooms (2 queen beds,1 double), 2 1/2 baths, plus outdoor shower, 3 decks, GRAND ROOM with dining table that seats ...
From $495 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Rustic Country Beach Cottage Candlewood Lake-Seasonal Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Property is Available for Seasonal Rental ONLY, June 1- August 30. A Magical Cottage, tastefully decorated with country ...
From $200 per night (USD)VRBO
- From $585 per night (USD)
VRBO
Direct Lakefront Home on Lake Lillinonah with Elevator Access
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Direct lakefront 3100 sq ft. home built in 2006 on exclusive Lake Lillinonah. This spacious and picturesque home is onl ...
From $585 per night (USD)VRBO
- From $1551 per night (USD)
VRBO
1 of a Kind “IronHorse Farm” All Inclusive retreat
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Nature & Luxury together at last! Newly renovated horse farm perfect for hosting groups of all sizes with every amenity ...
From $1551 per night (USD)VRBO
- From $1077 per night (USD)
VRBO
100% ROXBURY! PoshPadsCT \"SENTRY HILL\" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land ...
From $1077 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Cozy Organic Carriage House in Woods
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with ...
From $241 per night (USD)VRBO
- From $148 per night (USD)
VRBO
Cottage Retreat - Historic Cottage Home w Home Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
SPECIAL NOTE: Kindly message us for "Monthly Rates Discounts". The amazing cute historic cottage comfortably accommodat ...
From $148 per night (USD)VRBO
- From $2598 per night (USD)
VRBO
Stunning Warren Lakefront Home: Deck, Grill, Sauna
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 19
Bask in your own idyllic luxury at this spacious vacation rental named ‘Carriage House.’ Sitting on the banks of Lake Wa ...
From $2598 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Peaceful Goshen Cottage w\/ Screened Porch & Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Searching for the perfect spot to escape the worries of city life? Look no further than this peaceful 3-bedroom, 1.5-bat ...
From $230 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Cozy Litchfield House w\/ Fenced-In Yard & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Relish in the luxuries of this 3-bedroom, 2-bath Litchfield vacation rental! 'Stone-Peca' is the quintessential New Engl ...
From $377 per night (USD)VRBO
- From $283 per night (USD)
Expedia
Dainty New Preston Cottage w\/ Dock & Lake Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Visit the quiet shores of Lake Waramaug when you book this 3-bedroom, 2-bath New Preston vacation rental. This cottage p ...
From $283 per night (USD)Expedia
- From $3247 per night (USD)
VRBO
Grand Lakefront Home in Warren w\/ Expansive Patio!
- Bedrooms:
- 7
- Bathrooms:
- 9
- Sleeps:
- 19
Your ultimate family getaway awaits at 'The Boulders!' Situated on Lake Waramaug, this impressive 9-bedroom, 6.5-bathroo ...
From $3247 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
OPEN for Memorial Day! Our Connecticut retreat is equidistant from NYC and Boston and sits on 23 wooded acres with a ser ...
From $411 per night (USD)VRBO
- From $320 per night (USD)
VRBO
SUN HILL FARM 3\/4 MILE FROM LAKE WARAMAU
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Thank you for looking at the farm. The farm is located less than 3/4 mile from beautiful Lake Waramaug and the town beac ...
From $320 per night (USD)VRBO
- From $135 per night (USD)
VRBO
Historic House on Farmington River - An Angler’s Dream
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our Historic Barkhamsted house on Farmington River is a fly fisherman's paradise. Located directly across from famous f ...
From $135 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Expansive Countryside House, 7 Serene Acres with Pond & Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New look, newly painted living room! Expansive, light-drenched 3 bedroom house with large kitchen open to dining room se ...
From $338 per night (USD)VRBO
- From $999 per night (USD)
VRBO
Historic Estate on 40 Private Acres with Pool, Pond & Views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Fallen Fence is one of five original Whittlesey Mansions dating circa 1750 to 1800. The Whittlesey family settled the ar ...
From $999 per night (USD)VRBO
- From $913 per night (USD)
VRBO
Direct Waterfront on Candlewood Lake with \/ boat slip\/ hot tub & outdoor kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Candlewood Lake direct waterfront home offering beautiful panoramic views from every corner. This house and property ha ...
From $913 per night (USD)VRBO
- Click For Pricing
VRBO
STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w\/ Hot Tub & Pool Table!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 2
Classic, charming, and beautifully furnished, this stone "cottage" on Candlewood Lake, 70 miles north of NYC, is the per ...
Click For PricingVRBO
- From $399 per night (USD)
VRBO
Beautiful pet friendly riverfront vacation home on the Bantam River in Washington Depot
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This historic circa 1850s property once served as a gunsmith’s shop along the beautiful Bantam River just across from th ...
From $399 per night (USD)VRBO
- From $1088 per night (USD)
VRBO
BEST TOWN WASHINGTON! PoshPadsCT \"47CALHOUN\" 2Hrs NYC 4BR, Ski, Views,25-Acres
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1088 per night (USD)VRBO
- From $1117 per night (USD)
VRBO
100% ROXBURY! PoshPadsCT \"JUDD'S BRIDGE\" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land ...
From $1117 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Mabels Hollow Farm, En suite bedroom farm stay,
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This is not a whole house rental, please refer to house rental option. It is a large private loft room for a couple wi ...
From $147 per night (USD)VRBO
- From $472 per night (USD)
VRBO
Bluebird Valley Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bluebird Valley Farmhouse is handicap accessible on the ground floor with a full roll in shower , bathroom. A master b ...
From $472 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Salisbury Cottage Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect place for a weekend getaway in the Berkshires. Walking distance to Salisbury town, where you will find restaura ...
From $200 per night (USD)VRBO
- From $144 per night (USD)
VRBO
Victorian Guest Suite in heart of the Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2nd floor space located on Main St in a lovely Victorian Building. Lot's of light and country air! Off street parking. C ...
From $144 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront House and Artist's Studio in the Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perched on a bedrock ledge overlooking the Housatonic River, our house is a perfect summer getaway. The main house has o ...
Click For PricingExpedia
- From $404 per night (USD)
VRBO
Private hidden gem walking distance to town, restaurants, and shopping!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
High Street Hideaway Private hidden gem walking distance to town, restaurants, and shopping! 3BR/2BA - Pool, deck, gri ...
From $404 per night (USD)VRBO
- From $1085 per night (USD)
VRBO
BEST TOWN-WASHINGTON! NYC 2Hrs \"45 Calhoun\" POSHPADSCT Ski,Spa&Pool, Bikes,Views
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1085 per night (USD)VRBO
- From $646 per night (USD)
VRBO
Superb Lakefront Getaway with Family and Friends
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
YellowBird is our renovated home welcoming guests with vacation vibes on private, friendly Woodridge Lake, just minutes ...
From $646 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This completely remodeled cottage includes all amenities, complete kitchen accessories, linens, towels, washer & dryer ...
From $260 per night (USD)VRBO
- From $189 per night (USD)
VRBO
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This wonderful, first floor apartment is within walking distance to Lakeville lake. Walk to 5 restaurants, health food s ...
From $189 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Bantam Lake Cottage, Lake access, kayaks, fire pit, grill and games. solar power
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Large single-family one level cottage on a private lane with lake access including small shared beach, lawn and small do ...
From $371 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Kick back and relax in this calm, stylish apartment. This space offers fast internet, smart TV , a comfortable couch , ...
From $100 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Private home with stunning sunrise and sunset views.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Newly renovated Colonial with fully appointed gourmet kitchen, three bedrooms and three bathrooms, formal dining room, l ...
From $325 per night (USD)VRBO
- From $501 per night (USD)
VRBO
Available Month of August! Gracious Country Home in Washington, CT. \n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Just 90 minutes from NYC and Boston, Litchfield County is comprised of wonderful restaurants, unique shops, galleries, h ...
From $501 per night (USD)VRBO
- From $410 per night (USD)
VRBO
Stunning Litchfield home 1 1\/2 hours from NYC in idyllic setting, 3 bedrooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming newly renovated c1790 house on Old Mount Tom 1 1/2 hours from NYC! located between Lake Waramaug and Bantam Lak ...
From $410 per night (USD)VRBO
- From $199 per night (USD)
VRBO
Historic Estate - 5 min to Mohawk Mt Ski Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our enchanting country home, where the warmth of exposed wood beams and a charming wooden ceiling will captiv ...
From $199 per night (USD)VRBO
- From $668 per night (USD)
VRBO
FULL SUMMER SEASON RENTAL @ Woodridge Lake 4 Bed 3 Bath Tennis Beach Pool Gym
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Please read before sending inquiry. Available Summer 2024 **Summer is FULL SEASON only (NO WEEKLY or MONTHLY short term ...
From $668 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy upscale yet cozy accommodations in this 1734 farmhouse nestled in the northwest corner of Connecticut in the Litch ...
Click For PricingVRBO
- Click For Pricing
VRBO
Beautiful, family-friendly renovated farmhouse 6 minutes from skiing in Cornwall
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
Well-appointed antique farmhouse with recently renovated gourmet cook's kitchen, master BR suite with complete privacy a ...
Click For PricingVRBO
- Click For Pricing
VRBO
Relax in The Farmhouse on a a beautiful land & pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A lovely farmhouse located on 12 acres of farmland property. A view of nature offered greenery and beautiful lake make ...
Click For PricingVRBO
- From $750 per night (USD)
VRBO
Historic 1750's farmhouse w\/hot tub, outdoor fireplace and gym.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Set amongst sugar maples, enjoy this magnificently restored and modernized 1750 Farmhouse. This 3 bedroom (all with cath ...
From $750 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Lakefront Cottage w\/Dock, Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming lakehouse with dock, gorgeous views, swimming, kayaking, biking, hiking, or just kicking back and relaxing. Loc ...
From $417 per night (USD)VRBO
- From $1008 per night (USD)
VRBO
Litchfield County Four Season Country Paradise
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
3,800 Square foot beautifully furnished gated home with 220v Tesla Charger, large outdoor deck, chaise lounges for sixte ...
From $1008 per night (USD)VRBO
- From $846 per night (USD)
VRBO
100% WASHINGTON! PoshPadsCT \"SHEARER\"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you are searching for the perfect country setting within an easy drive to wonderful local restaurants, spas, shopping ...
From $846 per night (USD)VRBO
- From $1502 per night (USD)
VRBO
Live the good life in this luxury Lake Waramaug retreat!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Lake Waramaug Estate Liv ...
From $1502 per night (USD)VRBO