Chalet holiday rentals in Hartford

4.74 out of 5 average rating, 31 reviews

Chalet in Hillsdale

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.

4.94 out of 5 average rating, 417 reviews

Chalet in Otis

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

Chalet in Poughquag

4.97 out of 5 average rating, 74 reviews

The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

Chalet in Great Barrington

4.96 out of 5 average rating, 71 reviews

Berkshire "ZEN" Chalet

"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 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.

4.8 out of 5 average rating, 25 reviews

Chalet in Lenox

Peaceful Chalet in the Woods: Walk to Lenox

Family friendly, spacious cabin. Tons of natural light a wood stove and private garden. Woodsy feeling in contemporary setting next to Kennedy Park. Downstairs is mobility friendly w/ 1 twin ensuite, 1 Queen w/ separate full bath & TV room. Upstairs: Main bedroom with w/separate full bath and sitting area. Lovely deck, stunning views. Ping pong table and plenty of games for kids! 10 mins drive to Tanglewood, Kripalu; 8 min drive to Bousquet Ski Mtn., 15 to Red Lion & 25 to Butternut Mtn.

Top Guest favourite

Chalet in Monterey

4.98 out of 5 average rating, 84 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!

4.9 out of 5 average rating, 144 reviews

Chalet in Goshen

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 & stunning woods view, 10 minute drive to Woodridge Lake.

4.91 out of 5 average rating, 65 reviews

Chalet in Otis

Kayaks, Sauna & Family: Relax & Play

Join our unique Berkshire vacation experience, away from the hustle and bustle: 🌟Kayak & swim on the lake 🌟Boost wellness in our barrel Sauna 🌟Relax around the gas grill, pizza oven & firepit 🌟Minutes to restaurants & hiking 🌟Entertainment at Tanglewood (20 min) 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

4.85 out of 5 average rating, 20 reviews

Chalet in Housatonic

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!

4.95 out of 5 average rating, 40 reviews

Chalet in Holmes

Hudson Valley Lakeview Retreat - Lake Access

Relax and enjoy nature in this lakeside retreat! Only 75 minutes from Manhattan, with Metro North access nearby. Wake up to the sunrise over the lake with stunning views from the master bedroom; enjoy the private lake or one of many nearby hiking & biking trails; cook in the fully equipped kitchen or outdoor grill; and wind down with a bath in the jetted tub and a fire in the indoor wood stove or outdoor fire pit. UPDATE: Summer Lake view is back! Freshly trimmed trees and bushes.

4.89 out of 5 average rating, 38 reviews

Chalet in New Milford

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.

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Family-friendly chalet rentals

4.97 out of 5 average rating, 93 reviews

Chalet in Richmond

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago

This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.

4.55 out of 5 average rating, 11 reviews

Renovated One Bedroom Cottage by Ocean Beach

AlkaRating, 5 stars58 months ago

The cottage is ideally situated and worked well for my family for last minute weekend getaway to Hamptons. The place is super clean and tidy, the host and on site property manager is very responsive and helpful. The place is small and just as described, was comfortable for my family of four. I want to emphasize the place was really clean and tidy, a bit dated but had its own charm. We also had a covered patio so didn’t feel tight or cramped. The cottage is also less than 2 miles from the beach. I would recommend the place for a couple and for a family with two small children as a base to visit the Hamptons and surrounding areas.

Chalet in Lee

4.83 out of 5 average rating, 65 reviews

Waterfront lakehouse in Berkshires

LorriRating, 5 stars9 months ago

The chalet was perfect for our relaxing 5 day vacation. We enjoyed swimming off the dock and taking the kayaks out on the lake. The space is wonderful and the view is amazing! We found it hard to get motivated to go out to dinner and lunch because we didn't want to miss one second of the wonderful view!

4.31 out of 5 average rating, 13 reviews

Renovated Studio Cottage by Ocean

MattRating, 5 stars59 months ago

This was an absolutely fabulous place to stay! The grounds were in a lovely wooded area under the stars. Super clean, Bar B Q grill, great patio, large bed, fully functioning kitchen. Matt was excellent at providing information before hand, and responsive to queries. Super close to amazing hampton beaches, two mile hollow and beach lane. Also close to seafood mart with amazing lobster salad and a bagel place with iced coffee for the gays. Ask about the catch of the day. Loved it all!

Chalet in Killingly

4.86 out of 5 average rating, 22 reviews

Lake House in North Eastern CT

BarbaraRating, 5 stars8 months ago

Our family had a very nice time! Kids loved it. I definitely recommend it.

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars9 months ago

Absolutely amazing stay! I have never stayed with such hospitable and genuinely nice hosts. In addition their home was filled with interesting gadgets and beautiful aesthetic, they’ve inspired to replace every toilet in my house! I hope I have the pleasure of staying here again! Thank you Jennifer and Evan!

4.45 out of 5 average rating, 11 reviews

RenovatedOneBdrmCottageBy Ocean InHeartOf Hamptons

danielRating, 5 stars47 months ago

Great location, 1 mile from the beach They give you a beach parking pass, which is key!

Chalet in Canaan

4.56 out of 5 average rating, 68 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

RobinRating, 5 stars4 months ago

Great stay. Bathrooms r small and outdated but the fireplace and hot tub and property outweigh the cons.

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Luxury chalet rentals

Chalet in Hillsdale

5 out of 5 average rating, 3 reviews

Catamount Family Retreat - Walk to the Slopes

AlexandraRating, 5 stars3 weeks ago

Great house, perfect for our family. We stayed in the summer and it rained the whole time, but we still enjoyed it. The road is not very safe to walk on so definitely need a car to get around, but the restaurant right across the street at Little Cat was great. Overall really good place to stay, will be back

4.88 out of 5 average rating, 25 reviews

Chalet in Woodstock

"Nirvana": A Lakefront Retreat

JonneyRating, 5 stars9 months ago

Sandeep was an awesome host! He always responded promptly and even went out of his way to give me tour guide suggestions. Sandeep was always willing to help and made me feel appreciated. Sandeeps’s home was beautiful! The home was right near the water and there were even kayaks that Sandeep supplied to go kayaking. Peaceful area and beautiful scenery! So easy to check in and out.

MasonRating, 5 stars27 months ago

Enchanted Hamptons Cottage in NYTimes Garden

Dianne and her cottage are truly one of a kind! I enjoyed every moment of my stay. The house and property couldn’t be any more charming and the location is absolutely perfect- close to beach and town. I would recommend this place 10/10.

Chalet in Monterey

New Listing - Fully Renovated Lake/Ski Chalet

SuzannaRating, 5 stars3 months ago

This is a great house in a nice location. It’s comfortable, warm, well stocked kitchen, the jacuzzi was a nice touch have. Garry was a good host who was responsive and easy to work with.