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From $273 per night (USD)
VRBO
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Bedrooms:
1
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 $273 per night (USD)
VRBO
From $394 per night (USD)
VRBO
Cozy Lake Cottage with Hot Tub, Views, Kayaks
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Let the sun shine in! Bright and cozy cottage overlooking beautiful Candlewood Lake is perfect for all season getaways. ...
From $394 per night (USD)
VRBO
From $423 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 $423 per night (USD)
VRBO
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Expedia
Hudson Valley / 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, ...
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Expedia
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VRBO
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 ...
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VRBO
From $370 per night (USD)
VRBO
Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to an oasis of calm in the middle of nature within commuting distance of NY (1.30 hour drive and 20 mins to Metr ...
From $370 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Modern Ranch Retreat in Hudson Valley
Bedrooms:
1
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 $390 per night (USD)
VRBO
From $2785 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 $2785 per night (USD)
VRBO
From $469 per night (USD)
VRBO
The Art House: 5-Acre, Private Getaway with Fireplace
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 $469 per night (USD)
VRBO
From $478 per night (USD)
VRBO
Cozy family and pet friendly 3BR Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relax with the whole family at this peaceful place to stay just steps from Heritage Village and close to the town center ...
From $478 per night (USD)
VRBO
From $348 per night (USD)
VRBO
Cottage is currently rented for the year, and not available until further notice
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 $348 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Charming apartment 7 minute walk to 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 $276 per night (USD)
Expedia
From $412 per night (USD)
VRBO
The Blue Elm - A Historic Berkshire Cottage
Bedrooms:
1
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 $412 per night (USD)
VRBO
From $742 per night (USD)
VRBO
Bantam Beauty - Surrounded By Nature!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to the Bantam Beauty, a peaceful getaway located in the beautiful Litchfield Hills. Only 2 hours from NYC & you' ...
From $742 per night (USD)
VRBO
From $222 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 $222 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $253 per night (USD)
VRBO
Charming and Relaxing 4br Farmhouse for Group Getaway
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Step Back in Time at Our Rustic 4BR/2.5BA Farmhouse Getaway Looking for a peaceful escape into the countryside? Our sp ...
From $253 per night (USD)
VRBO
From $756 per night (USD)
Expedia
Country home vacation oasis with pool, hot tub, near lake/hiking.
Bedrooms:
1
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 $756 per night (USD)
Expedia
From $284 per night (USD)
VRBO
IDEAL LOCATION: Quiet 1-bedroom apartment, pool, garden, BBQ, lake view, hiking
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Discover serenity in the scenic hills of Litchfield County! This beautifully renovated one-bedroom apartment offers the ...
From $284 per night (USD)
VRBO
From $920 per night (USD)
Expedia
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
The outstanding POOL has been installed and IT IS operational in time for the next season. It boasts a wrap-around DECK ...
From $920 per night (USD)
Expedia
From $1329 per night (USD)
VRBO
Tranquil Contemporary Privacy
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
sunny contemporary retreat! This elegant 3-bedroom single-family residential house with a fully finished basement and t ...
From $1329 per night (USD)
VRBO
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Expedia
Charming renovated farmhouse with hot-tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Charming, beautifully renovated farmhouse perfect for ski visits, spring hikes and summer lakes. 10 mins to Mohawk ski. ...
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Expedia
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VRBO
Riverside Paradise in Litchfield
Bedrooms:
3
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 ...
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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 ...
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Expedia
From $269 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 $269 per night (USD)
VRBO
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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 ...
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Expedia
From $390 per night (USD)
VRBO
Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
This is a fabulous location that gives you classic New England charm with modern amenities. Enjoy staying in our cozy fa ...
From $390 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Creekside Retreat Tent
Bedrooms:
0
Bathrooms:
1
Sleeps:
8
Welcome to Creekside Retreat Tent at Freedom Farm Homestead Campground! Nestled beside our seasonal running creek and o ...
From $192 per night (USD)
Expedia
From $223 per night (USD)
VRBO
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Overlook near South Farms is a private, 1 bedroom apartment, located off a historical home in East Morris in Litchfi ...
From $223 per night (USD)
VRBO
From $1019 per night (USD)
VRBO
Stunning renovated horse farm with pool, hot tub, and 6 bedrooms.
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Bring your family to the stunning Iron Horse Farm, a gem in Morris, CT on 4 acres, steps from Litchfield and surrounding ...
From $1019 per night (USD)
VRBO
From $857 per night (USD)
VRBO
Modern Goshen House w/ Deck, Backyard & Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Set walking distance from the Goshen Fairgrounds, this spacious vacation rental house offers peace and quiet in addition ...
From $857 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Relax or be active! The choice is yours in this pet-friendly family home.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Whether you're looking for a place to relax, a place to play, or simply a place to rest your head, this is it. Our 3 bed ...
From $231 per night (USD)
Expedia
From $392 per night (USD)
VRBO
WOODBURY'S LAKE QUASSEPAUG SPRING-FED LAKE. DIRECT WATERFRONT. BOAT DOCK.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
SEASONAL RENTAL This true waterfront property sits on the West Shore of beautiful and tranquil Lake Quassapaug, a sprin ...
From $392 per night (USD)
VRBO
From $702 per night (USD)
VRBO
STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Gorgeous, recently renovated waterfront home on 8.5 acres with dock, hot tub, outdoor shower, gas grill, and smokeless f ...
From $702 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Magical woodland home, a property promising a serene getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked in the Litchfield Hills this property promises a serene getaway. Just 2 hrs from NYC, our post and beam home is ...
From $376 per night (USD)
VRBO
From $301 per night (USD)
VRBO
3-Bedroom Cabin Getaway With Rustic Charm
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This characteristic cabin getaway is located on a historic railroad street nestled in a charming village within the Hous ...
From $301 per night (USD)
VRBO
From $902 per night (USD)
VRBO
BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our family's lakefront log home sits on 1.4 acres with an amazing two-tiered deck, comfy couches and chairs, facing west ...
From $902 per night (USD)
VRBO
From $604 per night (USD)
Expedia
COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Bright and comfortable, our one level, midcentury home is surrounded by 4 acres of nature gardens and forest, with a sec ...
From $604 per night (USD)
Expedia
From $603 per night (USD)
VRBO
Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Hat Shop House! Only 90 mins from NYC, this charming New England farmhouse is the perfect place to get a ...
From $603 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Lovely lakeside house in peaceful, private setting amid New England's delights
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Plenty of room inside and out for family gatherings surrounded by nature's beauty, charming towns, and cultural activiti ...
From $383 per night (USD)
VRBO
From $409 per night (USD)
VRBO
CT Gate House Goshen CT, Gate House Goshen CT
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
<p>Private home on a large country estate where peace and serenity abound. Relax on the back porch with gorgeous views a ...
From $409 per night (USD)
VRBO
From $846 per night (USD)
VRBO
Spacious 5-bedroom house with Pool on 2 lovely acres
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Serene Country Estate on 2 lovely manicured acres. Featuring gunite pool, separate hot tub, serene pond, flower garden ...
From $846 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Nature Within Reach! Dear nature lover-Welcome to our woodland oasis, less than 2 hours from New York City! Enjoy the so ...
From $404 per night (USD)
VRBO
$Steele Brook Manor\nTranquil get away nestled \nin Litchfield County.$
From $209 per night (USD)
Expedia
Steele Brook Manor\nTranquil get away nestled \nin Litchfield County.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Steele Brook Manor is an old home with modern updates. Enjoy the tranquility of a dead end street with plenty of privat ...
From $209 per night (USD)
Expedia
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VRBO
Lakefront 3-bedroom house in lower Berkshires with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this delightful mid-century lake-front house on Twin Lakes in the foothills of the Berkshires. This relaxing v ...
Click For Pricing
VRBO
From $238 per night (USD)
VRBO
Walk to Memorial Park: Pet-Friendly Bethlehem Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dedicated Workspace | Walk to Restaurant w/ Live Music | 1 Mi to Long Meadow Pond Experience a captivating retreat in Be ...
From $238 per night (USD)
VRBO
From $575 per night (USD)
VRBO
Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
<p>You'll find a kayak on site at this smoke-free vacation home. With the property's convenient onsite parking, you'll b ...
From $575 per night (USD)
VRBO
From $4471 per night (USD)
VRBO
Crossroads Ranch Cornwall
Bedrooms:
12
Bathrooms:
8
Sleeps:
20
<p>Enjoy the countryside from this stately Cornwall estate on over a square mile of private land, featuring a 10-acre an ...
From $4471 per night (USD)
VRBO
From $903 per night (USD)
VRBO
The 1782 Darling House on the Litchfield Green
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Built in 1782 the Abel Darling House is nestled in the Litchfield historic district within steps of the Litchfield Green ...
From $903 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pet Friendly w/ Fee | 2 Kitchens | Washer & Dryer | 3 Mi to The Taft School This delightful 3-bedroom, 3-bath vacation ...
From $275 per night (USD)
VRBO
From $186 per night (USD)
VRBO
Private Room/Sunny/Clean/Peace/SelfCheckIn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A sunny clean second floor room with full-Queen size bed in a contemporary owner-occupied single-family house, charming ...
From $186 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Charming renovated 3-bedroom house in serene Winsted
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this cool, newly renovated house in picturesque Winsted. 4 minutes walk to Highland lake. With 3 bedrooms incl ...
From $239 per night (USD)
Expedia
From $2333 per night (USD)
VRBO
Argyll House by Boutique | Litchfield Escape
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Summary: This beautifully renovated estate, just two hours from New York City, is a refined family retreat that blends E ...
From $2333 per night (USD)
VRBO
From $448 per night (USD)
VRBO
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
The Spirit Horse Farm offers a unique and inspiring rental experience. Step into nature and enjoy generous amenities and ...
From $448 per night (USD)
VRBO
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VRBO
Peaceful Lakefront Oasis in Litchfield County
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our lovingly cared for lakefront home invites you for rest and relaxation. Jump off the dock for a swim or paddleboard / ...
Click For Pricing
VRBO
From $621 per night (USD)
Expedia
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Our cozy home welcoming guests with vacation vibes in the private, friendly Woodridge Lake community, just minutes from ...
From $621 per night (USD)
Expedia
From $857 per night (USD)
VRBO
Private Dock & Pool - Candlewood Lake
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to Candlewood Lake, a serene lakefront retreat in New Milford, CT. Enjoy stunning views of Candlewood Lake and se ...
From $857 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Riverside Farm
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax and refresh in this riverside retreat. One of a kind river frontage on the Farmington River. Private river access ...
From $430 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located on one of the prettiest streets in Washington CT and abutting 900+ acre Hidden Valley section of Steep Rock Pres ...
From $393 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our Little Creek Cabin is a place to pause. The cabin is located next to a rushing creek, where you can soak in a wood f ...
From $464 per night (USD)
Expedia
From $1963 per night (USD)
VRBO
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
-- HIGHLIGHTS-- ➳ Minutes from Kent Falls ➳ Mins from Squantz State Park ➳ 15 Minutes to Thunder Ridge Mtn. ➳ Dock, Pad ...
From $1963 per night (USD)
VRBO
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Expedia
Lakeside Oasis with Hot Tub; 5 min to Ski Mountain!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Hot tub up and running for the winter! Unwind above tranquil waters, marinate in the pool, bundle beneath the blanket a ...
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Expedia
From $627 per night (USD)
VRBO
Washington, CT Jewel! Charming Main House with separate Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Escape to Washington, CT—to this newly renovated vintage classic country style two-bedroom house in Washington and invit ...
From $627 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Bright and Spacious Secluded Forest Home with Sprawling Yard and Private Brook
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to "Gunn Brook Mountain House," a sun-filled mid-century home on 14 private acres with 1,000+ feet of brook front ...
From $310 per night (USD)
Expedia
From $922 per night (USD)
VRBO
Oak Manor, a luxurious property on 6,6 acres.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
High End Estate like property. Come enjoy the main part of this beautiful property located at 250 Westledge Drive, Tor ...
From $922 per night (USD)
VRBO
From $274 per night (USD)
Expedia
The Jefferson Guest House, Spacious, Special Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bask in this tranquil estate. Exceptional views, the sunrises are world class, many have said `the sky speaks to you he ...
From $274 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Harwinton lake house boasts 2 inviting bedrooms with 2 queen beds. (Cot available) The bathroom features a relaxing ...
From $216 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled at the edge of the Sharon Wildlife Area this 3 bedroom 2.5 bath home has an indoor pool and outdoor firepit. The ...
From $546 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Cozy Cottage in Historic Norfolk
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Unwind at this cozy cottage nestled in the historic village of Norfolk, CT. It is ideally situated on the edge of Barbou ...
From $244 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Lakefront Cottage in Connecticut - Hot Tub, Fire Pit, Game Room - Fall Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy 2BR/2BA lakefront cottage with hot tub, fire pit, and game room. Perfect fall retreat with foliage views, lake acce ...
From $253 per night (USD)
Expedia
From $1868 per night (USD)
VRBO
Upmarket Country Retreat, Washington, Connecticut
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
This private oasis offers a spacious and open floor plan that is perfect for relaxation. The living area seamlessly flow ...
From $1868 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Lakefront Charming Cottage Retreat, Bethlehem CT
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to Long Meadow Cottage, a peaceful lakeside retreat in historic Bethlehem, CT! Enjoy stunning water views, a full ...
From $376 per night (USD)
VRBO
From $228 per night (USD)
VRBO
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Our MCM Studio apartment is a one block walk to the picturesque village of Kent yet surrounded by fields, woods and is a ...
From $228 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Little Bell Cabin! A peaceful retreat where nature’s magic surrounds you. Whether you`re here to unwind, ...
From $397 per night (USD)
Expedia
From $143 per night (USD)
VRBO
Best Outdoors near the Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Looking for a quiet escape near the scenic Berkshires without being in the middle of tourist traffic? This cozy countrys ...
From $143 per night (USD)
VRBO
From $564 per night (USD)
VRBO
Cozy Getaway near Lake & Skiing; 2 min walk to lake; 10 mins to Mohawk Mountain
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This Goshen house boasts 4 inviting bedrooms with a variety of bed sizes to accommodate all guests. With 3 bathrooms, ev ...
From $564 per night (USD)
VRBO
From $374 per night (USD)
VRBO
The Farm Retreat House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A sprawling 5 acre landscape with views. 3-Bedroom, 2.5 Bath Farmhouse that has been fully renovated. An open concept l ...
From $374 per night (USD)
VRBO
From $1058 per night (USD)
Expedia
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Bedrooms:
3
Bathrooms:
6
Sleeps:
20
Discover Lakeside Oasis, a charming lakeside retreat on 2 private acres between Lake Lillinonah and Candlewood Lake, sle ...
From $1058 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Escape to this peaceful private home nestled in the heart of Barkhamsted's scenic woodlands, offering the perfect blend ...
From $409 per night (USD)
VRBO
From $1261 per night (USD)
Expedia
Modern 4BD Farmhouse in Litchfield w/ heated saltwater pool & jacuzzi, AC, WiFi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
At the end of a winding, tree-lined road, hidden from sight by towering pines and the gentle curve of the landscape, a c ...
From $1261 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Lakefront Oasis with Spectacular Views – 3BR, 3BA, Sleeps 6, private swim dock.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to this beautifully remodeled 4-season lakefront home, offering stunning panoramic views of the serene clear wate ...
From $506 per night (USD)
VRBO
From $639 per night (USD)
VRBO
New Lake Area Ski Season RentalWoodridge Lake, Near Litchfield and Mohawk Mtn
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Available for the long weekend or the full ski season! Available as soon as October 20, Christmas Week, Monteven monthly ...
From $639 per night (USD)
VRBO
From $348 per night (USD)
VRBO
Cozy Lake House - Salisbury/Lakeville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Near the charming towns of Salisbury and Lakeville, and within walking distance of Hotchkiss and Indian Mountain School, ...
From $348 per night (USD)
VRBO
From $572 per night (USD)
VRBO
A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perched on a small hill overlooking a picturesque New England town, this design-lover's retreat is a magical escape to e ...
From $572 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Woodland A-Frame
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your peaceful woodland retreat in Sharon, CT. This recently renovated, light-filled A-frame is nestled on 16 ...
From $334 per night (USD)
VRBO
From $246 per night (USD)
VRBO
Riverfront Paradise with Stylish Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stylish, newly renovated 900 sq. ft. one-room cottage overlooking pond and Housatonic River in scenic fly fishing estat ...
From $246 per night (USD)
VRBO
From $232 per night (USD)
VRBO
Hemlock Hill Suite - 1-bedroom apartment with WiFi, AC in lovely Litchfield
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the charm of Litchfield, Connecticut, and unwind in this beautifully designed guest suite, where modern luxury ...
From $232 per night (USD)
VRBO
Click For Pricing
Expedia
The Kent Collection - The Victorian - Whole House
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Built in 1890 and fully renovated in 2022, The Victorian is a spacious, elegant, and character-rich setting for family r ...
Click For Pricing
Expedia
From $341 per night (USD)
VRBO
Renovated Apartment on Main St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Enjoy small-town charm in the heart of Salisbury at this newly renovated apartment, designed by AIA award-winning archit ...
From $341 per night (USD)
VRBO
From $357 per night (USD)
VRBO
Dome Escape in Nature w/ Deck: 3 Mi to Kent Falls
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Dog Friendly w/ Fee | Dedicated Workspace | Near Farmers Markets Discover a one-of-a-kind retreat in Connecticut's Litc ...
From $357 per night (USD)
VRBO
From $757 per night (USD)
VRBO
Luxurious Private 5-Bedroom House with Sweeping Lake Views and Beach Access
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Perched on a hill with breathtaking lake views, this luxurious spacious retreat is just minutes from Lake Waramaug. Enjo ...
From $757 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Quaint & Historic 1760 Home Nestled In Nature, 10min to downtown Litchfield CT.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in a charming pocket of Litchfield, enjoy what this historic 1760, 2-bedroom home has to offer. With 1 king bed ...
From $423 per night (USD)
VRBO
From $1214 per night (USD)
VRBO
Whispering Estate Guest House - A Romantic Countryside Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2-bedroom guesthouse on the grounds of Whispering Estate. Perfect for couples, families, or bridal parties. Enjo ...
From $1214 per night (USD)
VRBO
$\nWhispering Estate – A Romantic Countryside Escape$
From $15201 per night (USD)
Expedia
\nWhispering Estate – A Romantic Countryside Escape
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Welcome to Whispering Estate, a stunning country retreat set on 70 private, manicured acres in the heart of Litchfield C ...
From $15201 per night (USD)
Expedia
From $816 per night (USD)
VRBO
Unique 4-bedroom house with stunning views, close to all in fantastic Cornwall
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Located in Cornwall, this house is a dream. Owned by 2 architects, it blends the historic old stone cottage with an exci ...
From $816 per night (USD)
VRBO
From $427 per night (USD)
VRBO
Spacious 4-bedroom house on riverfront; walk to delightful Washington, CT
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming, spacious 4BR, 1900 sqft riverfront home at end of dead-end road on 3 acres with a deep swimming hole, shady tr ...
From $427 per night (USD)
VRBO
From $741 per night (USD)
VRBO
Pool, Game Room, Movie Theater, Private Dock
Bedrooms:
5
Bathrooms:
4
Sleeps:
16
Escape to this serene Candlewood Lake home, available exclusively for mid-term rentals. This lakefront retreat features ...
From $741 per night (USD)
VRBO
From $978 per night (USD)
Expedia
Secluded Architectural gem in the heart of Roxbury - Modern, Chic & Dreamy Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Architectural Luxury Retreat in Roxbury — Designer Berm Home on 8 Secluded Acres with Heated Pool & Garden Oasis Tucked ...
From $978 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Cozy barn apartment in country setting in charming Litchfield
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
You will feel right at home in this bright and cozy guesthouse barn apartment. Bucolic setting with small country kitch ...
From $302 per night (USD)
VRBO
From $806 per night (USD)
VRBO
Hilltop Hideaway • Hot Tub, Views & Nature Trails
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Escape to the Berkshires and discover Hilltop Hideaway, a spacious 4-bedroom guesthouse perched atop a scenic hill in So ...
From $806 per night (USD)
VRBO

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