Chalet holiday rentals in Hartford

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Hartford

Guests agree: these chalets are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Superhost

The exterior of the lodge is framed by vibrant orange flowers and lush greenery, highlighting the natural setting. The wooden structure features a covered porch with a peaked roof, along with stone steps leading to the front entrance.

Chalet in Salem

4.68 out of 5 average rating, 82 reviews

3BR 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.

Top guest favourite

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

4.95 out of 5 average rating, 469 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

Top guest favourite

A spacious living area features large windows that provide ample natural light and views of the surrounding greenery. A cozy seating arrangement with patterned cushions is complemented by a stone fireplace and a rustic wooden shelf. A round coffee table is centered on a decorative area rug.

Chalet in Great Barrington

4.96 out of 5 average rating, 81 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.

The exterior of a charming house is displayed, featuring a steep, gabled roof and multiple levels. A spacious deck with white railings spans the front, adorned with hanging plants. Surrounding greenery includes colorful autumn foliage and a landscaped yard with patches of flowers.

Chalet in Hillsdale

4.86 out of 5 average rating, 65 reviews

Natural Splendor: Forest Luxury Retreat

Discover your perfect retreat near the heart of the Berkshires! This charming house offers tranquility year-round. In autumn, vibrant golds surround you; in winter, enjoy the warm fireplace while snow dances outside. The game room features pool and ping pong tables, and the spacious family room has surround sound and a 65" TV. Relax on the screened porch or large decks, gather around the fire pit, and enjoy a baby grand piano. Close to top attractions and restaurants, your ideal getaway awaits!

Chalet in West Stockbridge

4.95 out of 5 average rating, 44 reviews

Modern Mtn Chalet | Great Barrington & Tanglewood

Modern 3-BR Mountain Retreat. Sunlight-filled home (dining for 12) with cathedral ceilings in a secluded setting. Summer-ready: Large deck, screened porch, grill, firepit. 10 mins to Great Barrington/Stockbridge. Enjoy Tanglewood (20m), Norman Rockwell Museum (10m), Appalachian Trail hiking, and nearby lake swimming. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Culture: Near to galleries, antiques, historic homes, great dining, farmer's markets.

Guest favourite

An inviting vacation house features natural wooden siding and large windows, allowing light to pour into the interior. A small stone path leads to the entrance, surrounded by lush greenery and colorful flowers, creating a serene setting in the heart of the woods.

Chalet in Goshen

4.91 out of 5 average rating, 158 reviews

The Goshen Glass Chalet

A vacation Chalet with a smart lock,, furnished. Has a rustic flair, one large master bedroom down stairs and full bathroom. 1 full size bed & 2 twin size beds upstairs with a full bathroom. Well stocked & equipped kitchen, open large spacious combined living and a dining area with a fireplace and large screened TV with bose surround sound. Beautiful outdoor deck for dining screened in porch with a beautiful large patio, barbecue & fire pit. Woods view, 10 minute drive to the Lake.

Superhost

Chalet in Great Barrington

4.86 out of 5 average rating, 21 reviews

Screened Porch, River Views, Center of the Berks!

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

The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.

Chalet in Lenox

4.88 out of 5 average rating, 42 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

Your Modern Berkshires Escape Light-filled modern chalet next to Kennedy Park with beautiful views, a spacious living room, and a peaceful garden for morning coffee, evening wine or yoga. Designed for families and friends, with a private upstairs main suite plus comfortable guest rooms. Minutes to Tanglewood, downtown Lenox, hiking trails, lakes, great dining, and the best of the Berkshires. Perfect for a summer getaway filled with music, nature, and time to unwind. Healthy fun!

Chalet in Montauk

4.78 out of 5 average rating, 9 reviews

Montauk NY Walk To Ditch Plains Beach & ocean

Book any week (7 nights) between July and Labor Day and I will give you $1000 off Relax with the whole family at this peaceful place to stay near the ocean. 4 bedroom 2 bath home with plenty of outdoor decking and brick patio. Fire pit, hot tub, outdoor shower, two fireplaces, and just two city blocks from the beach. Also, we just recently installed a new five zone air-conditioning unit and heat pump. Air-conditioning and heat in every bedroom and living room. No pets allowed

Top guest favourite

Chalet in Otis

4.92 out of 5 average rating, 97 reviews

Family Lake Retreat | Sauna, Deck & Games

🚣 Kayak, swim, or float on the lake 🧖‍♂️ Relax in the Scandinavian barrel sauna 🍕 Grill, bake in the pizza oven, or gather around the firepit 🎶 Enjoy restaurants and Tanglewood (20 min) All Year Round: The light-filled interior offers comfort and style: 📺 Two large flat-screen TV (75" in Master bedroom, 80" in living room) 🍳 Fully equipped kitchen (air-fryer, waffle maker, Nespresso) 💻 Home office with fast WiFi 🎮 board games and outdoor arcade-style games and more

Top guest favourite

A cozy living room features two light-colored sofas adorned with decorative pillows. A wooden coffee table sits at the center, complemented by a woven area rug. A tall bookshelf filled with baskets is visible in the background, alongside a small side table and wall art.

Chalet in Monterey

4.98 out of 5 average rating, 93 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 high-speed broadband internet, capable of streaming & more!

Guest favourite

The open-plan living space features a wood-burning stove surrounded by comfortable seating. Expansive windows allow natural light to fill the room, showcasing the wooden interiors. A dining area with a table and chairs is visible, along with a cozy atmosphere enhanced by the surrounding greenery.

Chalet in Otis

4.9 out of 5 average rating, 21 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

Relax with the whole family at this peaceful 4 bedroom 3 bath chalet as your base to enjoy the great outdoors of the Berkshires. Close to lakes, hiking trails and just a short drive to Tanglewood and Jacob's Pillow. In winter Ski Otis Ridge a mile away, or a 25 minute drive to Butternut. Relax and enjoy family time in the open plan living space with wood burning stove and deck, or venture down to the firepit in the large secluded yard.