Litchfield Area Rentals
- From $500 per night (USD)
VRBO
NEW! Beautiful 3br vacation home at Woodridge Lake, Goshen, Litchfield County
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
New to market! Bring your loved ones (humans and fur-babies) together at this lovely home equipped with everything you ...
From $500 per night (USD)VRBO
- From $963 per night (USD)
VRBO
BEST TOWN! PoshPadsCT \"TUNNEL\" Ski!, 4-BR SPA-POOL, Bike, Hiking, NYC 1.5 Hrs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Roxbury & Washington are the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land pre ...
From $963 per night (USD)VRBO
- From $408 per night (USD)
VRBO
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- 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 $408 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Cozy Waterfront Cottage on Highland Lake, Northwestern CT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the 'Golden Nugget,' our cottage on Highland Lake, a 445-acre lake located in the rolling hills of Northweste ...
From $338 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $350 per night (USD)
VRBO
Check Out Cute Summer Cottage on Lake Warmaug
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
CURRENTLY AVAILABLE FOR: June 10 -20 September 8- November 1. FALL AVAILABLE Septem ...
From $350 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $1222 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 $1222 per night (USD)VRBO
- From $266 per night (USD)
VRBO
Private Kent Getaway With Views, Pond & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Close to the charming town of Kent, yet secluded on 9 acres, this cozy house provides all-season access to New England a ...
From $266 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Lake Waramaug Lake House - Ski Mohawk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Recently Renovated Lake Front property on exclusive Lake Waramaug in Washington CT. Enjoy all that Litchfield CT has to ...
From $500 per night (USD)VRBO
- From $889 per night (USD)
VRBO
BEST TOWN ROXBURY!1.5Hrs NYC PoshPadsCT \"TOPHET POOL BARN\" Ski,Pool,BBQ,Magical!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Spectacular Vaulted Beamed Ceiling Pool Barn with King Bed and Sleeper Sofa Rec Room & Office Area. Salt water heated p ...
From $889 per night (USD)VRBO
- From $917 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 $917 per night (USD)VRBO
- From $283 per night (USD)
VRBO
Secluded Cabin for the Perfect Weekend Escape
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax in our quiet, quaint & super cute cottage in Northwest Connecticut. Just 2 hours from NYC. Spend your days antiqui ...
From $283 per night (USD)VRBO
- From $986 per night (USD)
VRBO
BEST TOWN WASHINGTON PoshPadsCT \"SOUTH ST\" 2Hrs NYC, Mint, Pool, Ski, BBQ, Bike
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Washington is the best country rural retreat within 2 hours of NYC - the best restaurants, shopping, land preserves, Lak ...
From $986 per night (USD)VRBO
- Click For Pricing
VRBO
Barbell Brook
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful 750 sq ft walkout basement apartment is full of windows and sunlight. The unit has a master bedroom with ...
Click For PricingVRBO
- From $850 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 $850 per night (USD)VRBO
- From $250 per night (USD)
VRBO
The Perfect Escape From The City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perched on a rise in the beautiful lower Berkshires of Litchfield County, this house is your ideal escape from city life ...
From $250 per night (USD)VRBO
- From $125 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 $125 per night (USD)VRBO
- From $150 per night (USD)
VRBO
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 $150 per night (USD)VRBO
- From $1851 per night (USD)
VRBO
Nature & Luxury @Lavender Lake Est (Kosher optional)
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 20
Dream country home!! We recently purchased the ‘Lavender Lake Estate’ after a multi-year search for the perfect country ...
From $1851 per night (USD)VRBO
- From $1250 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 $1250 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Lakefront Winter Wonderland in New England Just 2 Hours From NYC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Inside Our Cabin (Central Air and Heat) We have a modern kitchen with a stainless steel dishwasher, fridge and range, ...
From $288 per night (USD)VRBO
- From $171 per night (USD)
VRBO
Enjoy colonial charm in one of Litchfield's oldest neighborhoods!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This property is conveniently located just a few steps from downtown Litchfield in the George Bolles home built in the 1 ...
From $171 per night (USD)VRBO
- From $270 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 $270 per night (USD)VRBO
- From $355 per night (USD)
VRBO
Cozy Log Cabin Retreat with Pool on 4 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gather at the log cabin in the woods and enjoy the private pool (Memorial Day - Sept). Updated with all the essentials l ...
From $355 per night (USD)VRBO
- From $544 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 $544 per night (USD)VRBO
- Click For Pricing
VRBO
Still Waters Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
DIRECT WATERFRONT-Dramatic western candlewood lake vistas with gorgeous sunsets & views from every room. Light and airy ...
Click For PricingVRBO
- From $225 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 $225 per night (USD)VRBO
- From $230 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 $230 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Adirondack-Style\/Cottage-Beautiful Lake & Mountain Views-Peaceful!
- Bedrooms:
- 1
- 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 $228 per night (USD)VRBO
- 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
- 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 $925 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 $925 per night (USD)VRBO
- From $903 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 $903 per night (USD)VRBO
- From $1309 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 $1309 per night (USD)VRBO
- From $706 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 $706 per night (USD)VRBO
- From $142 per night (USD)
VRBO
Private Lakeville\/Salisbury Converted Barn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
PLEASE NOTE LAKEVILLE LAKE IS NOW OPEN TO NON RESIDENTS $15/PERSON PER DAY CHILDREN UNDER ONE FREE INCLUDES PARKING --A ...
From $142 per night (USD)VRBO
- From $150 per night (USD)
Expedia
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 $150 per night (USD)Expedia
- From $513 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 $513 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 $671 per night (USD)
VRBO
FULL WINTER SEASON RENTAL @ Woodridge Lake 4 Bed 3 Bath 8 Minutes to Mohawk Ski
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Please read before sending inquiry. Booked full summer 2024, no availability. Now booking Winter 2025 as a FULL SEASON S ...
From $671 per night (USD)VRBO
- From $1239 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 $1239 per night (USD)VRBO
- From $675 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 $675 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 $357 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 $357 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 $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 $1136 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 $1136 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 $495 per night (USD)
VRBO
Pet & Kid Friendly, Solar, 13 Acres, Saltwater Pool, River Views, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
UNDER NEW MANAGEMENT: 3 bedrooms (3 queens), 2 1/2 baths, plus outdoor shower, 3 decks, GRAND ROOM with dining table th ...
From $495 per night (USD)VRBO
- Click For Pricing
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 $506 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 $506 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 $1208 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 $1208 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 $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 $691 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 $691 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 $100 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 $100 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
- From $309 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 $309 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 $912 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 $912 per night (USD)VRBO
- 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 $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 $355 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 $355 per night (USD)VRBO
- From $595 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 $595 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
- Click For Pricing
Expedia
Blackberry River Cottage: Where Fun & Nature Meet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make Unforgettable Memories at Our Family-Friendly Cottage. Indulge in homemade pizzas cooked in our original stone wood ...
Click For PricingExpedia
- Click For Pricing
Expedia
Enjoy Leaf Peeping from this Chic Waterfront Cottage.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Ideal location on the most coveted lake in Connecticut. This recently renovated 1940's lake cottage has full on lake vie ...
Click For PricingExpedia
- From $468 per night (USD)
VRBO
Close to Lime Rock, Prep Schools, 3 Ski Areas
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $468 per night (USD)VRBO
- From $146 per night (USD)
Expedia
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $146 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Private wooded family retreat with pool along picturesque river
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
AVAILABLE JULY 1st, 2023. Newly-built, architect-designed New England farmhouse with English Country interior on 14 acr ...
From $1400 per night (USD)VRBO
- From $200 per night (USD)
VRBO
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 $200 per night (USD)VRBO
- From $304 per night (USD)
Expedia
Cozy 2-bedroom Cottage with Access to Bantam Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This cozy, quaint cottage with dedicated Bantam Lake access is the perfect getaway for nature enthusiasts, cyclists, wri ...
From $304 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $341 per night (USD)
Expedia
Serene Salisbury Rental Home on 26 Acres w\/ Deck!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Relax, recharge, and repeat with a retreat to this serene Salisbury vacation rental! Featuring a prime location within w ...
From $341 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $900 per night (USD)
VRBO
Moody Pond House: 15 Min to Mohawk Ski Mountain, new country home on 18+ acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand new family friendly modern home with in-ground gunite pool set on 18.5 acres with a large pond. 5 minute drive fro ...
From $900 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Tranquil Country Setting in Litchfield County
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Very private location with lots of room and within minutes of lots of summertime activities. Imagine yourself sitting ...
From $180 per night (USD)Expedia
- From $199 per night (USD)
VRBO
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 ...
From $199 per night (USD)VRBO
- From $72 per night (USD)
Expedia
Tranquil Freedom Farm Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to Freedom Farm Campground! Nestled on 13 acres, our serene oasis offers a unique retreat amidst picturesque lan ...
From $72 per night (USD)Expedia
- From $695 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 $695 per night (USD)VRBO
- From $200 per night (USD)
Expedia
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 $200 per night (USD)Expedia
- From $395 per night (USD)
VRBO
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 $395 per night (USD)VRBO
- From $1650 per night (USD)
Expedia
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 ...
From $1650 per night (USD)Expedia