Chalet vacation rentals in The Berkshires

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Top-rated chalet rentals in The Berkshires

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Guest favorite

Chalet in Cragsmoor

5.0 out of 5 average rating, 226 reviews

Scandinavian-Style Chalet with Scenic Views

Wake up to hilly views from this Scandinavian-inspired chalet boasting wood-paneled cathedral ceilings, sharp furnishings, and concrete floors. Share a glass of wine with a friend beside a sleek fireplace and live-edge coffee table in a chic living area. Please inform the host if you plan to bring a dog as there is a 20 pound weight limit. Maximum number of guests/visitors/people permitted on the property is 2. Our current housekeeping policy since Covid-19 is we block our calendar a minimum of two days after each guest checks-out for cleaning and disinfecting. Polished concrete floors with radiant heat, 8 ft. tall windows, 10 ft. walls, wood vaulted ceiling, air conditioning, gas fireplace fully equipped kitchen (oven, stove, refrigerator, dish washer, coffee maker, microwave, toaster, ninja) washer and dryer. Full bathroom with tile and marble. Free Wi-Fi, 50" smart tv The chalet is a free standing private building with a deck and covered porch. It has it's own barbecue, hammock and fire pit for your private use. Guests have full access to the owners 20 acre property which includes some short trails through the woods and an outdoor shower. The owner lives on the property in a seperate residence and is available for any assistance guests require. The chalet is set in an area of seclusion on the Shawangunk Mountains in Cragsmoor. A short drive away is the entrance to Sam's Point Preserve with miles of hiking trails and incredible scenic views. Effective 5/1/22 a reservation is required to enter Sam’s Point on the weekend. Go to ReserveAmerica. com to make a reservation. Minnewaska State Park and Mohonk Preserve are nearby. Dining and shopping are within a five to ten minute drive. There is no public transportation nearby so the only way to get to us is by motor vehicle. If your coming up during the winter season a four wheel drive vehicle is highly recommended. The owner has two cats that live on the property. The cats are never permitted inside the chalet.

Feb 23 – Mar 2

R7,841 ZAR per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 351 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

Jul 19 – 26

R7,494 ZAR per night

Guest favorite

Chalet in Hurley

4.98 out of 5 average rating, 182 reviews

Exquisite Chalet,Woodstock best scenery, Generator

Newly renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir view, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden for you to sample. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.

Jan 21 – 28

R4,087 ZAR per night

Guest favorite

Chalet in Cummington

4.86 out of 5 average rating, 101 reviews

Berkshire A-Frame Chalet!

Our secluded home is just off of route 9 in Cummington. We are less than 1 hour away from many attractions including Tanglewood, Mass MoCA, Glendale Falls and Northampton. This area is not only beautiful for hiking, but also motorcycle riding here is exquisite! No wifi or cable (plenty of movies!), good cell phone coverage for Verizon and AT&T (tMobile has not worked in the past, but recently guests have said that it does work). Friendly pets welcome! 1 pet maximum. We abut Shire Village Camp.

Jul 6 – 13

R3,219 ZAR per night

Guest favorite

Chalet in Gilboa

4.97 out of 5 average rating, 103 reviews

3BR/2BA Chalet w/ Unforgettable Views on 22+ Acres

A nature-lover's paradise, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (17 mi), Catskill (26 mi) and downtown Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills.

May 8 – 15

R4,589 ZAR per night

Guest favorite

Chalet in Napanoch

4.95 out of 5 average rating, 206 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our 29 recsue goats, chickens, dogs and of course, local wildlife!

Mar 2 – 9

R3,179 ZAR per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Sep 20 – 27

R2,859 ZAR per night

Guest favorite

Chalet in Big Indian

4.95 out of 5 average rating, 107 reviews

The Alpine Chalet - A Cozy, Catskill Mountain Home

Enjoy the scenic Catskill Mountains in this Bavarian-style chalet situated on half an acre with valley views. Composed of modern luxuries and comforts, The Alpine Chalet is the perfect getaway for anyone looking to explore the Catskills. Only 6 mins to Full Moon Resort, 10 mins to Belleayre Ski Mountain, and 15 mins to Phoenicia/30 mins to Woodstock, an abundance of hiking trails, ski resorts, and charming towns await you! Follow us on Insta! @Alpine.Chalet STR License #2022-STR-AO-005

Jul 11 – 18

R4,548 ZAR per night

Guest favorite

Chalet in Maplecrest

4.96 out of 5 average rating, 221 reviews

Windham Chalet w BBQ Hut and Pizza Oven

Private, yet just five minutes from Windham, our house offers an escape from day to day stress. It has 3 bedrooms, one with a queen bed on the first floor and upstairs a bedroom with 2 twin beds and one bedroom with 2 bunk beds. Outside a large deck with Adirondack chairs and a small bar table with chairs, gas grill and swing bed are some of the things you can enjoy .In rainy weather you can sit on the large covered deck, observe nature, swing on the bed, grill or gather around the fire.

Dec 15 – 22

R7,324 ZAR per night

Guest favorite

Chalet in Tannersville

4.96 out of 5 average rating, 196 reviews

Romantic Chalet~ Hot Tub ~ Near Hunter Mountain

The Catskills Hideaway is a place to step back in time, unwind with a cocktail by the fire, soak in the hot tub, read a book in one of the hanging chairs, toast marshmallows with friends, prepare a special meal in the kitchen, ski your heart out, hike one of the many local trails, visit the falls, enjoy the local restaurants- whatever you’re dreaming about for your Catskill escape- this is THE PLACE! Hunter Mountain 4.8 miles Windham Mountain 12.6 miles Kaaterskill Falls 4 miles

Sep 26 – Oct 3

R5,901 ZAR per night

Guest favorite

Chalet in Hunter

4.92 out of 5 average rating, 308 reviews

Big Timber Lodge - Hunter Mountain’s TOP Getaway

Discover why our guests have left over 275 five star reviews! This 3-story custom log home sits perched on a beautiful running creek for the perfect weekend or midweek getaway. Featuring a premium outdoor hot tub, fire pit area and truly unforgettable views. Our home offers two units each with three bedrooms, kitchen, indoor jacuzzi, fireplace and plenty of games. The staircase to the creek brings you steps away from a meditative nature walk, trout fishing and zen relaxation.

Oct 27 – Nov 3

R19,879 ZAR per night

Guest favorite

Chalet in Saugerties

4.98 out of 5 average rating, 136 reviews

A-Frame Chalet in the Heart of the Hudson Valley

Set back on a private road surrounded by tall trees, The Chalet is a three bedroom, three bathroom A-frame house in close proximity to all the main attractions of the Catskills and Hudson Valley. Perfect for a weekend getaway or an extended stay, and great for couples and families. The house has three levels, each with its own bedroom, bathroom and common area. Relax by the fire pit, sip morning coffee on the deck, read a book in the loft, or take a walk in the woods.

Aug 18 – 25

R4,971 ZAR per night