Chalet vacation rentals in Sullivan County

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Top-rated chalet rentals in Sullivan County

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

Guest favorite
Chalet in Cragsmoor
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.
Aug 15 – 22
$368 per night
5.0 out of 5 average rating, 226 reviews
Guest favorite
Chalet in Lackawaxen
Secret Getaway Nestled in a Woodland Setting
Less than 1 mile to Beautiful community pool/restaurant/tiki bar! Lake and beach available for guests! Waterfall hikes! Along with so much more! Please reach out with any specific questions! Our home and the area are truly beautiful! Less than 2 hours from NYC! Our 1200 sqft chalet offers beautiful hardwood floors throughout, modern kitchen & bathrooms, cozy wood stove, oversized bedrooms, large wooded lot, huge outdoor wraparound deck, wireless internet, 3 roku tv’s (one in living area, one in the master bedroom & one in game room) & ample parking! Bumper pool & poker in the game room. New charcoal grill! Kayaks available to bring to river (2 minutes away) or community lake that offers beaches, boat launch, and restaurant (life vests must be worn at all times). Pets Welcome! :) Ski Big Bear less than a mile from the house! Open for the season (weather permitting) The home is located in the Masthope ski community, meaning there are many amenities for your enjoyment. By summer enjoy the lake, outdoor pool, restaurant and, of course, the tiki bar. There are stables for horse riding, a market for shopping and a large recreation area featuring tennis courts, a bocce ball court, a racquetball court, miniature golf and much more. We have also made our kayaks available for guests to use but PLEASE wear a life vest! Delaware river access less than a minute away and lake access 5 minutes. By winter you can ski, snowboard and snow tube as much as you wish and there are also cross-country trails to explore. With your guest pass, you will have access to all the amenities at Masthope. You have the entire chalet to yourselves. We live locally so if there is anything you need or have any questions regarding area recommendations, please don’t hesitate to ask :) We welcome both short and long term bookings Pets Welcome!
Mar 13 – 20
$165 per night
4.92 out of 5 average rating, 392 reviews
Guest favorite
Chalet in Grahamsville
Chalet in the mountains with a breathtaking view!
Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love
Jul 3 – 10
$218 per night
4.96 out of 5 average rating, 137 reviews

Popular amenities for Sullivan County chalet rentals

Family-friendly chalet rentals

Superhost
Chalet in Callicoon
Majestic Farmland A-Frame with Sweeping Views
May 12 – 19
$206 per night
4.84 out of 5 average rating, 210 reviews
Chalet in Jeffersonville
Jeffersonville NY Secluded Catskill Cabin
Jun 30 – Jul 7
$197 per night
4.83 out of 5 average rating, 155 reviews
Guest favorite
Chalet in Bethel
Relaxing Lakefront, Very Clean, Great for Families
Oct 26 – Nov 2
$338 per night
4.94 out of 5 average rating, 33 reviews
Chalet in Jeffersonville
Family Get-A-Way - 10min to Bethelwoods
Nov 21 – 28
$336 per night
4.82 out of 5 average rating, 34 reviews
Guest favorite
Chalet in Lackawaxen
Masthope Mountain - Poconos - Lake & Ski Community
Jun 7 – 14
$257 per night
4.98 out of 5 average rating, 57 reviews

Luxury chalet rentals

Guest favorite
Chalet in Monticello
Catskills Lakefront Escape with Hot Tub
Oct 15 – 22
$968 per night
4.9 out of 5 average rating, 97 reviews
Superhost
Chalet in Lackawaxen
Luxury 2 Master Suite with Hot & Sauna
Dec 23 – 30
$731 per night
4.83 out of 5 average rating, 18 reviews
Guest favorite
Chalet in Bethel
150 acre Luxury Eco-Retreat - Renewable powered!
Mar 14 – 21
$869 per night
4.94 out of 5 average rating, 31 reviews
Guest favorite
Chalet in Glen Spey
Petals & Pines - Lakeside Log Home
Jul 10 – 17
$650 per night
4.88 out of 5 average rating, 8 reviews
Superhost
Chalet in Monticello
Modern Chalet with Hot Tub and Lake Access
Aug 11 – 18
$680 per night
4.81 out of 5 average rating, 69 reviews

Lakefront chalet rentals

Superhost
Chalet in Liberty
Lovely Liberty Chalet On the Waterfront
Nov 8 – 15
$339 per night
4.73 out of 5 average rating, 41 reviews
Guest favorite
Chalet in Lackawaxen
Bella Vista Chalet Poconos -Ski Resort/Fireplace
May 12 – 19
$233 per night
5.0 out of 5 average rating, 20 reviews
Superhost
Chalet in Glen Spey
Mayflower - Lake access/hot tub/game room/pets
Feb 22 – Mar 1
$416 per night
4.88 out of 5 average rating, 95 reviews
Guest favorite
Chalet in Lackawaxen
Waterfront Chalet in Masthope!
Apr 20 – 27
$291 per night
4.79 out of 5 average rating, 14 reviews
Chalet in Lackawaxen
Eagle Rock Pond Chalet for a Memorable Getaway
Apr 13 – 20
$303 per night
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