Chalet holiday rentals in Hartford

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Hartford

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Chalet in Hillsdale

4.75 out of 5 average rating, 32 reviews

Contemporary chalet on 11 acres

Charming chalet situated on the top of a wooded hillside, with a long, private driveway and 11 acres of woods with pond and nature trails. Short drive to Hudson & Great Barrington. Open plan living area has large sectional, stunning morning light, Hue lighting + hip decor. Kitchen has new stainless steel appliances. Two bedrooms upstairs, and TV room/office lead to expansive, private deck with hot tub and furniture for relaxing and enjoying nature. Downstairs lounge has a bar, couch, TV and gym.

Chalet in Salem

4.68 out of 5 average rating, 81 reviews

3BR Adirondack Guest House on 36 Acre waterfront

3br bedroom Adirondack lodge, complete with wrap around porch on our 36 acre waterfront estate. Updated kitchen with island bar and laundry. WiFi, high speed internet+fire tv. NewCentralAC. Estate featured on HGTV and The Wall Street Journal. “Salem Woods” on Gardner Lake features an amazing shared indoor 8000 sq. Year round:salt water pool & spa, hot tub, sauna, & steam room. Enjoy: walking trails, half a mile of private sandy beach, 2 docks, fire pits, canoes, kayaks, fishing, water sports.

Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 426 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Superhost

Chalet in Great Barrington

4.96 out of 5 average rating, 74 reviews

Berkshire "Zen" Cottage

"ZEN" Palace Chalet perfect spot to chill & relax after a day of exploring or skiing. SPACIOUS,secluded,quiet, great grounds -3 bdrm 2 ba with LUSH VIEWS endless windows. BEAUTIFUL exposed wood beams & ceilings throughout. Super family friendly. 5 min GREAT BARRINGTON, Butternut, Catamount, great food, nature trails, lakes, great shopping & farmer's markets. Close to STOCKBRIDGE,Tanglewood, Norman Rockwell Museum, Wheatleigh, Kirpalu,Canyon Ranch & HUDSON NY. Accessible knowledgable local host.

Superhost

Chalet in Otis

4.91 out of 5 average rating, 70 reviews

Starry Skies, Sauna & Smores: YOUR Fall getaway

Unique Berkshire vacation experience, away from the hustle and bustle: 🍁Boost your wellness in the barrel Sauna 🍁Relax around the grill, pizza oven & firepit 🍁Mingle around our 80” TV & gas fireplace 🍁Minutes to restaurant & hiking 🍁Kayak & swim (weather permitting) The newly designed light-filled interior offers comfort and style while being perfectly suited for children: 👉fully equipped kitchen (air-fryer, waffle maker, Nespresso) 👉home office (Fast Wifi) 👉arcade-style games and more

Top guest favourite

Chalet in Copake

4.98 out of 5 average rating, 65 reviews

Private upstate home nestled in the Hudson Valley

Recently renovated chalet-style home located in Copake New York 10 minutes from Copake Lake. Modern design meets country living. Centrally located with access to the Berkshires, Hudson, Catamount Ski Resort, Bash Bish recreation area and more! This 3-bedroom, 2-bath home sits on 3.5 acres of landscaped grounds with beautiful western views, garden patio, wrap-around deck, fire pit, modern amenities, central air, and outdoor games. Set back from the road, the property is private and secluded.

Top guest favourite

Chalet in Monterey

4.98 out of 5 average rating, 87 reviews

Cozy French Country chalet

Perfectly situated, this cozy French Country chalet is minutes to downtown Monterey, Lake Garfield & just 10 minutes to Butternut for skiing. Family friendly, this home is stocked with games, movies & books for a fun-filled trip. If you're looking for a relaxing Berkshires getaway, look no further than this well-cared-for home, stocked with amenities to make your trip comfortable & relaxing! The home also has upgraded Internet with 2 internet satellite dishes, to handle Zoom calls & home work!

Top guest favourite

Chalet in Goshen

5 out of 5 average rating, 55 reviews

North Goshen A-Frame

This beautiful A-Frame is nestled on 4.5 acres in the charming NW corner of Connecticut. Situated adjacent to 800 acres of state forest and just 8 miles from Mohawk Mountain Ski Area, this location offers numerous hiking trails and walking paths, making it a haven for outdoor enthusiasts! Local attractions include: Mohawk Mountain Ski Area, Goshen Fair Grounds, Action Wildlife, Sunset Meadow Winery, Nodine's Smokehouse, Thorncrest Milk House Chocolates, Infinity Music Hall, Lime Rock Park

Guest favourite

Chalet in Goshen

4.9 out of 5 average rating, 146 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & fire pit woods view, 10 minute drive to the Lake.

Superhost

Chalet in Great Barrington

4.85 out of 5 average rating, 20 reviews

River Views, Screen Porch, Sun Deck, Fire Pit!

Conway House: Conway House: Brand New Contemporary Chalet with 3 Bedrooms, 2.5 baths and sparkling river views! Sleeps 6 (8 max). Screened porch, central AC, propane wood stove, 2 HDTVs, 2 car garage with direct entry, propane grill, outdoor seating with solo wood stove, high speed internet, good cell service, washer/dryer, whole-house water filter for clean drinkable water, decks with river views and plenty of outdoor seating! All linens included. Pets considered. No Smoking, please!

Guest favourite

Chalet in New Milford

4.9 out of 5 average rating, 42 reviews

Candlewood Lake Vacation Home | jj chalet

Modern A-frame home on the northern end of Candlewood Lake in New Milford, CT. Only 1.5h drive from NYC, making this the perfect nature escape for families or small groups . Whether you're taking out the kayaks, going for a hike on miles of open trails, or relaxing by a cozy fire on the deck, you're bound to make some incredible memories here at jj chalet. Pet friendly w/ fee (must be listed on reservation) 3 bedroom / 2 bath 4 wheel drive vehicles required for winter travel.

Chalet in Woodstock

4.9 out of 5 average rating, 29 reviews

"Nirvana": A Lakefront Retreat

Summer is here, now's the time to enjoy a lakefront getaway! Discover our rustic oasis amidst the treetops of Woodstock, Connecticut! Magnificent views in every corner; a spacious open floor plan with kitchen, living room and dining room; 2 private bedrooms; a large outside deck; and gorgeous Witches Woods Lake make Nirvana the perfect place to relax and enjoy nature. IMPORTANT: Nirvana is meant for small, relaxed getaways. Please review the house rules before booking.