Litchfield Area Rentals
From $472 per night (USD)VRBO
County Seat Colonial
- Bedrooms:
- 1
- 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 $472 per night (USD)VRBO
From $338 per night (USD)Expedia
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 $338 per night (USD)Expedia
Click For PricingVRBO
Bright and Sunny Direct Waterfront with Private Sandy Beach -
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This contemporary and fully equipped home is modern with an open floor plan. It sits on the picturesque west shoreline o ...
Click For PricingVRBO
From $300 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 $300 per night (USD)VRBO
From $261 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 $261 per night (USD)VRBO
From $564 per night (USD)VRBO
Spacious family home with open floor plan...close to lake and clubhouse!
- Bedrooms:
- 2
- 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 $564 per night (USD)VRBO
From $753 per night (USD)VRBO
An acclaimed photographer's country home, near private schools!
- Bedrooms:
- 2
- 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 $753 per night (USD)VRBO
From $505 per night (USD)Expedia
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 $505 per night (USD)Expedia
From $810 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 $810 per night (USD)VRBO
From $447 per night (USD)Expedia
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
My home has all the casual comfortable amenities for your perfect family/friends getaway. It's one that you'll want to r ...
From $447 per night (USD)Expedia
From $830 per night (USD)VRBO
NEW Modern Estate, Pool, Theater + Peloton
- Bedrooms:
- 3
- 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 $830 per night (USD)VRBO
From $716 per night (USD)VRBO
Long Meadow Manor, Heated Pool, Family game room, Apple picking and Lake nearby
- Bedrooms:
- 2
- 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 $716 per night (USD)VRBO
From $576 per night (USD)VRBO
Private Country Retreat in Lovely Lakeville CT
- Bedrooms:
- 2
- 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 $576 per night (USD)VRBO
From $443 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 $443 per night (USD)VRBO
From $164 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 $164 per night (USD)VRBO
From $407 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 $407 per night (USD)VRBO
From $297 per night (USD)VRBO
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 $297 per night (USD)VRBO
From $979 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 $979 per night (USD)VRBO
From $327 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 $327 per night (USD)VRBO
From $154 per night (USD)VRBO
Sweet Beehive Cottage / Berkshire Foothills. Minimum 15 days
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Charming, Rustic, Casual Summer Home set in the middle of a nature preserve. This cottage is simple but fully furnished ...
From $154 per night (USD)VRBO
From $576 per night (USD)VRBO
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 $576 per night (USD)VRBO
From $413 per night (USD)VRBO
A Haven in the Country-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sprawling country home located in historic Washington, CT. 90 minutes from New York City and Boston, Litchfield County ...
From $413 per night (USD)VRBO
From $640 per night (USD)VRBO
Secluded retreat, 13 acres, solar, pool, river views, pet & child friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Soaring ceilings, open floor plan, and expansive windows bring the calm of nature indoors, creating a serene space to u ...
From $640 per night (USD)VRBO
From $1249 per night (USD)VRBO
\"SENTRY HILL\" Best Town 1.5 hrs NYC PoshPadsCT Mint 6BR, Heated Pool, Bike, BBQ
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land ...
From $1249 per night (USD)VRBO
From $417 per night (USD)VRBO
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 100
Relish in the luxuries of this 3-bedroom, 2-bath Litchfield vacation rental! 'Stone-Peca' is the quintessential New Engl ...
From $417 per night (USD)VRBO
From $432 per night (USD)Expedia
Dainty New Preston Cottage w/ Dock & Lake Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Screened-In Porch | Lake Views | Seasonal Private Dock Visit the shores of Lake Waramaug at this New Preston vacation r ...
From $432 per night (USD)Expedia
From $494 per night (USD)VRBO
Expansive Countryside House, 7 Serene Acres with Pond & Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect summer escape! Expansive, light-drenched 3 bedroom house with large kitchen open to dining room seating 12. Cath ...
From $494 per night (USD)VRBO
From $940 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 $940 per night (USD)VRBO
From $1245 per night (USD)VRBO
\"Calhoun 3-4BR\" 2 Hrs NYC -Best Town, Land, Views, Restaurants, Pool, PoshPadsCT
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1245 per night (USD)VRBO
From $1245 per night (USD)VRBO
\"Judds Bridge 5BR\" Best Town ROXBURY 1.5 Hrs NYC! PoshPadsCT, HeatedPool, GasBBQ
- 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 $1245 per night (USD)VRBO
From $338 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 $338 per night (USD)VRBO
From $746 per night (USD)VRBO
Litchfield Hills Lakefront Vacation Home!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
YellowBird is our renovated home welcoming guests with vacation vibes on private, friendly Woodridge Lake, just minutes ...
From $746 per night (USD)VRBO
From $477 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 $477 per night (USD)VRBO
From $404 per night (USD)VRBO
Bantam Lake Cottage - 4 min walk to lake/shared beach, 6 Kayaks, 2 SUP, fire pit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***Summer of 2026*** - Bantam Lake Cottage has been rented all summer. Please message if you are looking for a 1-3 mont ...
From $404 per night (USD)VRBO
From $206 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 cozy space offers fast internet, smart TV , a comfortable cou ...
From $206 per night (USD)VRBO
From $711 per night (USD)VRBO
Summer Open for Booking! Woodridge Lake Tennis Pool Gym Beach 4 Bed/3 Bath AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your Perfect Summer 2026 Lake House Escape Awaits! Now open for Summer 2026, all weeks available, minimum stay is 2 wee ...
From $711 per night (USD)VRBO
From $1151 per night (USD)VRBO
Litchfield County Four Season Country Paradise
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
3,800 Square foot beautifully furnished gated home with 220v Tesla Charger, large outdoor deck, chaise lounges for sixte ...
From $1151 per night (USD)VRBO
From $2905 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 $2905 per night (USD)VRBO
From $1245 per night (USD)VRBO
\"Kirby\" Best 10 Star Home, Historic Green Walking Location! 2HrsNYC, BBQ,Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highest rated historic Carriage House in the best location. Washington is the best country rural retreat within 2 hours ...
From $1245 per night (USD)VRBO
From $204 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 $204 per night (USD)VRBO
From $309 per night (USD)VRBO
Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
“ROARING BEAR” cabin a fully restored and updated Adirondack style cabin originally built in 1922, situated on a pine fo ...
From $309 per night (USD)VRBO
From $516 per night (USD)Expedia
Historic Colonial...Close to Village Green
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feels like home! This classic 1860's colonial is the perfect place to unwind and enjoy all Litchield has to offer. The ...
From $516 per night (USD)Expedia
From $400 per night (USD)VRBO
Cozy Log Cabin Retreat with Pool on 4 Acres
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Gather at the log cabin in the woods and enjoy the private pool (Memorial Day - Sept). Updated with all the essentials l ...
From $400 per night (USD)VRBO
From $930 per night (USD)VRBO
PoshPadsCT 2Hrs NYC,Tennis, Mohawk Mt & Lake 5 Mi. \"MELIUS 1BR+Sofa Bed COTTAGE\"
- Bedrooms:
- 1
- 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 $930 per night (USD)VRBO
From $283 per night (USD)VRBO
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A charming lakefront cottage in the foothills of the beautiful Berkshire Mountains. Located on a peaceful lake with a pr ...
From $283 per night (USD)VRBO
From $267 per night (USD)VRBO
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom lakefront cottage with private dock on very quiet, picturesque lake, private beach area within walking distanc ...
From $267 per night (USD)VRBO
From $694 per night (USD)VRBO
NEW! Woodridge Lake Gem! Sunny, spacious, recently updated contemporary home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located in the heart of Litchfield County, easy 2 hour drive from either NYC or Boston. This tri-level gem is nestled by ...
From $694 per night (USD)VRBO
From $1854 per night (USD)Expedia
Candlewood Lake Retreat with Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
About this space Candlewood Lake Retreat with Private Dock, Game Room & Firepit Escape to Candlewood Lake for peaceful ...
From $1854 per night (USD)Expedia
From $1874 per night (USD)VRBO
House Nestled Bet Vineyards/Pool, Sauna and Spa
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This country home is located in one of the most beautiful streets in the Lake Waramaug area. Views from the two Vineyard ...
From $1874 per night (USD)VRBO
From $338 per night (USD)Expedia
Litchfield County Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated country house situated on 4.8 acres of wooded land with a broad, natural lawn, and apple trees. It's ...
From $338 per night (USD)Expedia
From $321 per night (USD)VRBO
Lakefront Fall Foliage 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 $321 per night (USD)VRBO
From $388 per night (USD)Expedia
Charming 1870 cape cottage in Litchfield
- Bedrooms:
- 1
- 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 $388 per night (USD)Expedia
From $317 per night (USD)VRBO
Two Bedroom Cottage Close To Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $317 per night (USD)VRBO
From $513 per night (USD)Expedia
Gather your family at this country estate
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Judd Farm – A Spacious Country Retreat on 33 Acres Tucked into the rolling hills of Litchfield County, Judd ...
From $513 per night (USD)Expedia
From $194 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 $194 per night (USD)VRBO
From $248 per night (USD)Expedia
Guest Cottage on Country Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $248 per night (USD)Expedia
Click For PricingVRBO
Nature & Luxury @Lavender Lake Est (Kosher optional)
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 20
Dream country home!! We recently purchased the ‘Lavender Lake Estate’ after a multi-year search for the perfect country ...
Click For PricingVRBO
From $350 per night (USD)VRBO
Private Kent Getaway With Views, Pond & Pool
- Bedrooms:
- 1
- 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 $350 per night (USD)VRBO
From $1245 per night (USD)VRBO
\"Painter Hill\" Best Town 1.5 Hrs NYC, Restaurants, Shops,VIEWS! Hot Tub Spa, BBQ
- 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 $1245 per night (USD)VRBO
From $412 per night (USD)VRBO
Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our cottage on Highland Lake, a 445-acre lake located in Winsted (Winchester), nestled in the rolling hills o ...
From $412 per night (USD)VRBO
From $1247 per night (USD)VRBO
\"Senff 5BR\" 2 Hrs NYC, Best Town, Restaurants, Shops, PoshPadsCT, HotTub, Skiing
- 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 $1247 per night (USD)VRBO
From $659 per night (USD)VRBO
One of the Original Summer Cottages on Lake Warmaug
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
August Special. $300 per night. New Expanded Deck for great outside living. Propane BBQ. Lots of seating for lazy ...
From $659 per night (USD)VRBO
From $581 per night (USD)VRBO
Charming country home in Roxbury
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming country retreat located in the beautiful northwest corner of the Litchfield hills in bucolic Roxbury, CT. Roxb ...
From $581 per night (USD)VRBO
From $1248 per night (USD)VRBO
\"MOOSEHORN\" 1.5HrsNYC, Best Town, Restaurants, Shopping - Heated Pool PoshPadsCT
- 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 $1248 per night (USD)VRBO
From $657 per night (USD)VRBO
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 $657 per night (USD)VRBO
From $478 per night (USD)VRBO
Beautiful antique gem- The oldest house in Litchfield CT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Idyllic antique country cottage in a private setting. Cozy as it gets, and convenient to everything the area has to off ...
From $478 per night (USD)VRBO
From $1245 per night (USD)VRBO
\"Tunnel\" HEATED SPA-POOL Best Location! 1.5 Hrs NYC! PoshPadsCT Bike, Hike, Ski
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Roxbury & Washington are the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land pre ...
From $1245 per night (USD)VRBO
From $237 per night (USD)VRBO
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the Beauty of Roxbury, Connecticut Unwind in the hills at this peaceful and private loft nestled above a barn ...
From $237 per night (USD)VRBO
From $492 per night (USD)VRBO
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 $492 per night (USD)VRBO
From $576 per night (USD)Expedia
Hilltop House
- Bedrooms:
- 2
- 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 $576 per night (USD)Expedia
From $1456 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 $1456 per night (USD)VRBO
From $1425 per night (USD)VRBO
\"Kielwasser 5BR\" 2Hrs NYC,Best Town,Restaurants! HeatedPool,BBQ,4FPs, PoshPadsCT
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $1425 per night (USD)VRBO
From $921 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 $921 per night (USD)VRBO
From $2590 per night (USD)VRBO
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 $2590 per night (USD)VRBO
From $318 per night (USD)VRBO
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 $318 per night (USD)VRBO
From $359 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 $359 per night (USD)VRBO
From $640 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 $640 per night (USD)VRBO
From $2193 per night (USD)VRBO
6-Acre Luxurious Country Home with Goddess Point Lookout
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Set atop a beautiful lookout, this exquisite Woodbury home warmly welcomes you for your next vacation stay. The perfect ...
From $2193 per night (USD)VRBO
From $1247 per night (USD)VRBO
\"MELIUS\" Warren-Washington NYC 2Hrs, 5BR Mint, Heated Pool, Tennis, 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 $1247 per night (USD)VRBO
From $472 per night (USD)VRBO
Fickle Fox Farm. It’s snow season! Lifts are open. Fireplace is crackling!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Newly renovated three bedroom, two and half bath home on 6 bucolic acres in Canaan Valley, CT. Located at the base of th ...
From $472 per night (USD)VRBO
From $518 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 $518 per night (USD)VRBO
From $180 per night (USD)Expedia
Charming, river front compound
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront terraces, Large living room with propane fireplace and french doors to river. Large dining room, with firepl ...
From $180 per night (USD)Expedia
From $349 per night (USD)VRBO
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 $349 per night (USD)VRBO
From $361 per night (USD)Expedia
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 ...
From $361 per night (USD)Expedia
From $332 per night (USD)VRBO
2023-2024 Academic Listing Connecticut Farm House With Breathtaking Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Monthly rental for the 2023-2024 academic calendar from September 6, 2023 through the May 31, 2024. Fully renovated 191 ...
From $332 per night (USD)VRBO
From $305 per night (USD)VRBO
Country living with a Lake View
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
A delightful year round cottage dog-friendly vacation home nestled in the Litchfield Hills at the base of the Berkshires ...
From $305 per night (USD)VRBO
From $375 per night (USD)VRBO
Rustic cabin on private pond and 7 acres! Woodstove, porch for wildlife viewing
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rustic cabin in Colebrook, Ct in beautiful Litchfield County...less than mile to Massachusetts border and Camp Jewel! ...
From $375 per night (USD)VRBO
From $413 per night (USD)VRBO
Waterfront modern oasis under 2 hours from NYC. Lots to enjoy summer and fall!
- 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 $413 per night (USD)VRBO
From $1305 per night (USD)VRBO
Expansive, Five Bedroom House with Pool. Ideal for Multiple Family Travel
- Bedrooms:
- 4
- 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 $1305 per night (USD)VRBO
From $632 per night (USD)VRBO
Historic Litchfield Hills Saltbox on Large Estate!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
On the ground floor you will enjoy a fully-equipped kitchen, a living room with game space, a cozy tv room, a full bathr ...
From $632 per night (USD)VRBO
From $460 per night (USD)VRBO
Mountain View Getaway
- Bedrooms:
- 3
- 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 ...
From $460 per night (USD)VRBO
From $1906 per night (USD)VRBO
Sunny Ridge - Best Town & Estate 2 Hrs NYC, Heated Pool, Restaurants, PoshPadsCT
- Bedrooms:
- 7
- 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 $1906 per night (USD)VRBO
From $646 per night (USD)VRBO
Summer Lake Cottage, private beach, Berkshire Hills, small village
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 18
This is the lake cottage your grandmother visited during her childhood. Charming, original 1920 features. Big remodeled ...
From $646 per night (USD)VRBO
From $446 per night (USD)Expedia
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 ,2 queen, 2 twins , queen futon and double p ...
From $446 per night (USD)Expedia
From $1171 per night (USD)VRBO
Fabulous year round waterfront retreat on Lake Waramaug
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $1171 per night (USD)VRBO
From $1151 per night (USD)Expedia
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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 $1151 per night (USD)Expedia
From $302 per night (USD)VRBO
1st Floor The Inn at Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Inn at Highland Lake. This first floor unit of the lakehouse offers a fully furnished 1-bedroom 1-bathroo ...
From $302 per night (USD)VRBO
From $314 per night (USD)Expedia
2nd Floor The Inn at Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the Inn at Highland Lake. This second floor unit of the lakehouse offers a fully furnished 3-Bedroom 1-Bathro ...
From $314 per night (USD)Expedia
From $980 per night (USD)VRBO
Candlewood Lake Front with Dock,Chef's Kitchen. Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This is a newly constructed home with now expense spared directly on Candlewood Lake. It has a amazing Chef's Kitchen w ...
From $980 per night (USD)VRBO
From $344 per night (USD)VRBO
Beautiful and Roomy Country Setting
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is available to be your temporary home. Quiet setting with huge country kitchen (full appliances and with lots ...
From $344 per night (USD)VRBO