Chalet vacation rentals in Hartford

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Top-rated chalet rentals in Hartford

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The exterior of the chalet is bathed in warm evening light, surrounded by trees. A large umbrella shades the deck, which includes seating and decorative elements. The entrance is framed by bright windows, contributing to a cozy and inviting appearance.

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.

Guest favorite

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, 439 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

Guest favorite

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, 76 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.

Top guest favorite

An aerial view of the chalet-style home reveals a spacious wrap-around deck with multiple seating arrangements, illuminated by string lights. The landscaped grounds are surrounded by trees, featuring an outdoor fire pit nearby and a garden area visible in the background.

Chalet in Copake

4.99 out of 5 average rating, 68 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 favorite

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, 89 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!

Guest favorite

Chalet in Otis

4.91 out of 5 average rating, 77 reviews

Thrill & Chill: Ski & Sauna in Winter Wonderland

Join our unique Berkshire vacation experience, away from the hustle and bustle: ❄️Minutes to ski (Otis Ridge), 20 min to Butternut ❄️Boost your wellness in the barrel sauna ❄️Relax around the gas fireplace ❄️Binge your fav show on the 80” TV ❄️Min. to restaurant & snow shoeing 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

Top guest favorite

A charming A-frame house is surrounded by lush greenery, with a stone path leading to its inviting front door. A soft rainbow arcs over the structure, complementing the natural setting, while trees frame the property, highlighting its serene outdoor atmosphere.

Chalet in Goshen

5 out of 5 average rating, 72 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 favorite

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

4.9 out of 5 average rating, 148 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

An open-concept living area features high wooden ceilings and large windows that frame views of the Housatonic River. A wooden dining table accommodates several chairs, while comfortable seating is arranged around a coffee table. French doors lead to the outdoor deck, enhancing the space's connection to nature.

Chalet in Housatonic

4.85 out of 5 average rating, 20 reviews

Sunset Views: Screened 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 favorite

An A-frame designer home is surrounded by lush greenery, featuring large glass windows that invite natural light. A spacious deck is accessible from the main entry, and neatly landscaped grass frames the property, enhancing its tranquil outdoor setting.

Chalet in North Fork

5 out of 5 average rating, 13 reviews

A-Frame by the Water

Escape to a luxury fall retreat at our stunning designer chalet, nestled near Peconic Bay in Greenport NY. With 4 bedrooms, 3 baths, and a warm cozy loft, this space is perfect for a crisp autumn getaway, team retreat or weekend recharge. Sip cider by one of two fireplaces, visit the local apple orchards, wineries and farms, or take a brisk walk on the beach just steps from the house. Enjoy the quiet charm of the area from the comfort of this serene, design-forward haven.

Guest favorite

A wooden gazebo overlooks Witches Woods Lake, framed by lush green trees. The structure features a decorative roof and a circular table surrounded by chairs, creating an inviting outdoor space to enjoy the serene water views.

Chalet in Woodstock

4.91 out of 5 average rating, 32 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.

Guest favorite

A modern kitchen is presented with sleek, dark cabinetry and stainless steel appliances. A large window provides natural light, while a geometric light fixture hangs overhead. The open design features a view into the living space, showcasing a blend of stone and wood elements.

Chalet in New Marlborough

4.93 out of 5 average rating, 55 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

Enjoy privacy at a cozy mountain home on 40 acres, minutes from ski resorts and shops. Floor-to-ceiling windows offer stunning views. This pet-free retreat is ideal for families seeking adventure & relaxation. Kids enjoy the playroom and outdoor space while parents relax in the jacuzzi tub or comfy living area. The fully stocked kitchen makes meal prep simple. Friendly local hosts provide restaurant tips, babysitter bookings and insider advice to enhance your stay.