Litchfield Area Rentals
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
From $868 per night (USD)VRBO
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 $868 per night (USD)VRBO
From $1136 per night (USD)VRBO
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 $1136 per night (USD)VRBO
From $724 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 $724 per night (USD)VRBO
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)VRBO
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)VRBO
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 $505 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 $505 per night (USD)Expedia
From $323 per night (USD)VRBO
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)VRBO
From $956 per night (USD)Expedia
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 $956 per night (USD)Expedia
From $382 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 $382 per night (USD)VRBO
From $333 per night (USD)VRBO
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)VRBO
From $854 per night (USD)VRBO
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 $854 per night (USD)VRBO
From $356 per night (USD)Expedia
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 $356 per night (USD)Expedia
From $174 per night (USD)VRBO
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 $174 per night (USD)VRBO
From $207 per night (USD)Expedia
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 $207 per night (USD)Expedia
From $2363 per night (USD)VRBO
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 $2363 per night (USD)VRBO
From $891 per night (USD)VRBO
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 $891 per night (USD)VRBO
From $997 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 $997 per night (USD)VRBO
From $302 per night (USD)VRBO
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)VRBO
From $359 per night (USD)VRBO
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 $359 per night (USD)VRBO
From $1351 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 $1351 per night (USD)VRBO
From $608 per night (USD)VRBO
Check Out Cute Summer Cottage on Lake Warmaug
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Late Summer Deal. due to recent cancellation. Rate reduction. ONLY $285 per day. CURRENTLY AVAILABLE FOR: A ...
From $608 per night (USD)VRBO
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 $1191 per night (USD)VRBO
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 $1191 per night (USD)VRBO
From $270 per night (USD)VRBO
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
A charming lakefront cottage in the foothills of the beautiful Berkshire Mountains. Located on a peaceful lake with a pr ...
From $270 per night (USD)VRBO
From $238 per night (USD)VRBO
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
2 bedroom lakefront cottage with private dock on very quiet, picturesque lake, private beach area within walking distanc ...
From $238 per night (USD)VRBO
From $348 per night (USD)VRBO
Cozy Log Cabin Retreat with Pool on 4 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gather at the log cabin in the woods and enjoy the private pool (Memorial Day - Sept). Updated with all the essentials l ...
From $348 per night (USD)VRBO
From $542 per night (USD)VRBO
WARREN PoshPadsCT \"MELIUS 1BR+Sofa Bed COTTAGE\" Ski Mohawk-5Mi!,2Hrs NYC,Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Mint country 1-BR Cottage on Warren's most scenic walking street. Shared Tennis Court, First floor living room, queen sl ...
From $542 per night (USD)VRBO
From $278 per night (USD)VRBO
Adirondack-Style\/Cottage-Beautiful Lake & Mountain Views-Peaceful!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
“ROARING BEAR” cabin a fully restored and updated Adirondack style cabin originally built in 1922, situated on a pine fo ...
From $278 per night (USD)VRBO
From $1374 per night (USD)VRBO
100% WASHINGTON! PoshPadsCT \"SENFF ESTATE\"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 15
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1374 per night (USD)VRBO
From $796 per night (USD)VRBO
100% WASHINGTON! PoshPadsCT \"KIRBY\" 2HrsNYC, 3BR, Spa, Ski, Walking Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $796 per night (USD)VRBO
From $256 per night (USD)VRBO
Litchfield Hills Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full ...
From $256 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $546 per night (USD)VRBO
Lakefront Cottage w\/Dock, Kayaks
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming lakehouse with dock, gorgeous views, swimming, kayaking, biking, hiking, or just kicking back and relaxing. Loc ...
From $546 per night (USD)VRBO
From $1189 per night (USD)Expedia
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 $1189 per night (USD)Expedia
From $953 per night (USD)VRBO
100% WASHINGTON! PoshPadsCT \"SHEARER\"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
If you are searching for the perfect country setting within an easy drive to wonderful local restaurants, spas, shopping ...
From $953 per night (USD)VRBO
From $668 per night (USD)VRBO
The Summer House @ Woodridge Lake 4 Bed 3 Bath Pool Tennis Pickle Beach Gym
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Please read before sending inquiry. Now booking Summer 2025 as a FULL SEASON summer house rental. **Now booking Summer ...
From $668 per night (USD)VRBO
From $1173 per night (USD)VRBO
BEST TOWN-WASHINGTON! NYC 2Hrs \"Calhoun5BR\" 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 $1173 per night (USD)VRBO
From $790 per night (USD)VRBO
Litchfield Hills Lakefront Home! Amazing location, views and sunsets
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
YellowBird is our renovated home welcoming guests with vacation vibes on private, friendly Woodridge Lake, just minutes ...
From $790 per night (USD)VRBO
From $385 per night (USD)VRBO
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This completely remodeled cottage includes all amenities, complete kitchen accessories, linens, towels, washer & dryer ...
From $385 per night (USD)VRBO
From $435 per night (USD)VRBO
Bantam Lake Cottage - 4 min walk to lake\/shared beach, 6 Kayaks, 2 SUP, fire pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large single-family one level cottage on a private lane with lake access including small shared beach/lawn, this is a 3- ...
From $435 per night (USD)VRBO
From $1173 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 $1173 per night (USD)VRBO
From $1053 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 $1053 per night (USD)VRBO
From $474 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 $474 per night (USD)VRBO
From $695 per night (USD)VRBO
Litchfield County Farmhouse Retreat in Vineyard Area
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 5
Our home is a 1790s Federal Colonial located in the heart of Litchfield County. Vineyards, Mohawk ski resort, a covered ...
From $695 per night (USD)VRBO
From $1272 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 $1272 per night (USD)VRBO
From $253 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 $253 per night (USD)VRBO
From $154 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 $154 per night (USD)VRBO
From $1173 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 $1173 per night (USD)VRBO
From $514 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 $514 per night (USD)VRBO
From $641 per night (USD)VRBO
Secluded retreat,13 acres, Solar, Pool, River Views, Pet & Child Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
UNDER NEW MANAGEMENT: 3 bedrooms (3 queen beds), 2 1/2 baths, plus outdoor shower, 3 decks, GRAND ROOM with dining tabl ...
From $641 per night (USD)VRBO
From $368 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 $368 per night (USD)VRBO
From $354 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 $354 per night (USD)VRBO
From $759 per night (USD)VRBO
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Prana Residence-Spa is a holistically designed residence provides total relaxation and the transformation of vital life ...
From $759 per night (USD)VRBO
From $304 per night (USD)Expedia
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming cottage retreat, a haven for food enthusiasts and nature lovers alike. Our renovated cottage fe ...
From $304 per night (USD)Expedia
From $853 per night (USD)VRBO
Direct Water Front Home, Private Boat Dock, Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Fully furnished direct waterfront single family home with Westerly views. 3 bedrooms, 2 full bathrooms, and living room ...
From $853 per night (USD)VRBO
From $413 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 $413 per night (USD)VRBO
From $297 per night (USD)VRBO
Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Charming, traditional cottage design fully renovated and modernized, located among the very best of locations at H ...
From $297 per night (USD)VRBO
From $132 per night (USD)VRBO
Sweet Beehive Cottage \/ Berkshire foothills. MONTHLY RENTAL \/ minimum 20 days
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Charming, Rustic, Casual Summer Home set in the middle of a nature preserve. This cottage is not fancy, but fully furni ...
From $132 per night (USD)VRBO
From $396 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 $396 per night (USD)VRBO
From $1176 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 $1176 per night (USD)VRBO
From $739 per night (USD)VRBO
Super comfy, chic converted barn with saltwater pool on 6 acres.
- 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 $739 per night (USD)VRBO
From $439 per night (USD)Expedia
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 $439 per night (USD)Expedia
From $274 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 $274 per night (USD)VRBO
From $297 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 $297 per night (USD)VRBO
From $211 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 $211 per night (USD)VRBO
From $458 per night (USD)VRBO
Spacious family home with open floor plan, fireplace…and close to ski area!
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $458 per night (USD)VRBO
From $570 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 $570 per night (USD)VRBO
From $1520 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 $1520 per night (USD)VRBO
From $436 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 $436 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
From $182 per night (USD)VRBO
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Inn at Highland Lake! This first floor unit sleeps up to 4 guests, and offers a fully furnished 1-Bedroom ...
From $182 per night (USD)VRBO
From $285 per night (USD)Expedia
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Inn at Highland Lake! This second floor unit sleeps up to 8 guests, and offers a fully furnished 3-Bedroo ...
From $285 per night (USD)Expedia
From $692 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 $692 per night (USD)VRBO
From $311 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 $311 per night (USD)Expedia
From $394 per night (USD)VRBO
Cozy 2-bedroom Cottage with Access to Bantam Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy, quaint cottage with dedicated Bantam Lake access is the perfect getaway for nature enthusiasts, cyclists, wri ...
From $394 per night (USD)VRBO
From $431 per night (USD)Expedia
Serene Salisbury Rental Home on 26 Acres w\/ Deck!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 11
Relax, recharge, and repeat with a retreat to this serene Salisbury vacation rental! Featuring a prime location within w ...
From $431 per night (USD)Expedia
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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 ...
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From $287 per night (USD)Expedia
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 ...
From $287 per night (USD)Expedia
From $282 per night (USD)VRBO
Hidden Serenity at TuKasa - Pool & Billiards
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About this space Discover serenity in our private nestled in the heart of Litchfield County. Embrace tranquility surroun ...
From $282 per night (USD)VRBO
From $902 per night (USD)VRBO
BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT
- Bedrooms:
- 4
- 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 $676 per night (USD)VRBO
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 $676 per night (USD)VRBO
From $810 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 $810 per night (USD)VRBO
From $276 per night (USD)VRBO
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 $276 per night (USD)VRBO
From $557 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 $557 per night (USD)Expedia
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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 ...
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From $755 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 $755 per night (USD)Expedia
From $231 per night (USD)VRBO
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 $231 per night (USD)VRBO
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Spacious 4-bedroom condo with AC and WiFi in Litchfield County
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Stay comfortably in Litchfield County at this 4-bedroom condo. This condo features modern amenities like a washing mach ...
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From $192 per night (USD)VRBO
Creekside Retreat Tent
- Bedrooms:
- 1
- 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)VRBO
From $112 per night (USD)Expedia
RIVERSIDE HOMESTEAD on the Farmington River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Peaceful getaway, newly remodeled riverfront studio apartment that sleeps 3(1 Qn bed, 1 couch for small child) comfortab ...
From $112 per night (USD)Expedia
From $351 per night (USD)VRBO
Bright and 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 ...
From $351 per night (USD)VRBO
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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 / ...
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From $202 per night (USD)VRBO
1 bedroom in a factory converted loft, with fitness room, WiFi in Torrington
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Torrington apartment boasts 1 inviting bedroom. With amenities like a fitness room, coin laundry, WiFi, heating, an ...
From $202 per night (USD)VRBO
From $232 per night (USD)VRBO
Cozy Blue Bungalow on the Lake, Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Get ready to relax in this cozy 3-bedroom bungalow in Sharon. This fabulous property features 2 queen beds and 1 twin be ...
From $232 per night (USD)VRBO
From $397 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 $397 per night (USD)VRBO
From $468 per night (USD)Expedia
Bellhaven- Charming 4-bedroom house in Canaan, CT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Keep it simple in the East wing of this 220 year old Greek Revival home in Canaan. This brilliant house offers a queen b ...
From $468 per night (USD)Expedia
From $408 per night (USD)VRBO
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $408 per night (USD)VRBO
From $489 per night (USD)Expedia
Escape to a one-of-a-kind Mountaintop Retreat with panoramic westerly views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Revel in the awe-inspiring scenery and sunsets in this tranquil haven nestled amidst nature's embrace. The main floor fe ...
From $489 per night (USD)Expedia