Vacation rentals in Cragsmoor

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Top-rated vacation rentals in Cragsmoor

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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 7 – 14

G$88,276 GYD per night

Guest favorite

Cabin in Phillipsport

4.97 out of 5 average rating, 180 reviews

The Pond House - A modern cabin within the forest.

A modern, private cabin secluded within a private 19 acres, just 90 miles away from New York City ! This stunning home was designed by Sundial Studios Architecture & Design, and was featured both within Dwell Magazine (google: wabi sabi weekend cabin) and the NY Times (google: haiku of a home). This 3 bedroom 2 bath cabin was developed in response to the beautiful landscape it is placed within and is surrounded by forest and wildlife, overlooking a pond. Follow us on Instagram - @pond.place

Apr 29 – May 4

G$117,110 GYD per night

Superhost

Home in Bloomingburg

4.81 out of 5 average rating, 460 reviews

Δ Scenic Hiking Paradise with Deck and Fire Pit!

Relax at this peaceful place atop the Shawangunk Mountain Ridge. You'll enjoy plenty of room at this wooded oasis! • On 2 wooded acres • Beautiful area • Deck off kitchen w nice grill • Lawn fire pit w seating & string lights • Adjacent to 1600 acres of State Forest with official hiking trails & Amazing Views right near house • EXTRA Professional Covid Cleaning • Home gym & treadmill • 3 bedrooms • Large living room with 2 sleeper sofas • Near great outdoor and indoor attractions

Apr 26 – May 3

G$29,024 GYD per night

Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 418 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Jan 29 – Feb 5

G$26,954 GYD per night

Guest favorite

Guest suite in Kerhonkson

4.95 out of 5 average rating, 127 reviews

Private Apt. in Vintage House steps to Kerhonkson.

Your private sunlit upstairs apt. features magical views of The Catskills. Pets are welcome. One room is a master bedroom with a workspace, TV and huge closets. The second room has a full kitchen (gas stove, fridge/ freezer, sink) large table, sofa that folds out to a full size bed. Use of fire pit, back yard, cafe size tables, outside chairs for your convenience. Unlimited free access to Minnewaska State Park, (save $10 fee). The house is walking distance to town and the Rail Trail. Welcome!

May 5 – 12

G$18,272 GYD per night

Guest favorite

Home in Napanoch

5.0 out of 5 average rating, 157 reviews

Cozy Home on the Hill (Welcome to the country!)

This cozy spacious renovated home is surrounded by nature yet not far off the beaten path. It is situated facing east toward the Shawangunk Mountain where the sun beams its rays over as it rises. Its the perfect location to get away from the hustle and bustle with a large level private yard for games or just sit and let natures residents serenade you. At night, look up at the vast sky and gaze at the stars and planets or sit at a warm mesmerizing fire to lull you to sleep. Get out and enjoy!

Feb 23 – Mar 2

G$30,553 GYD per night

Superhost

Home in Pine Bush

4.85 out of 5 average rating, 118 reviews

5 Acre Modern Mountain A-Frame with Barn

A stone’s throw from the Hudson valley wine trail and state parks, this modern A-frame is set on a 5 acre former horse farm, providing privacy without seclusion. 2 hrs from NYC, it’s perfect for weekend trips or longer getaways. An ideal day here can include a morning coffee on the wraparound deck, working remotely with an amazing pastoral view, exploring the barn, hiking one of many nearby trails, and ending the night roasting marshmallows under the stars and unwinding in the clawfoot tub.

Oct 21 – 28

G$90,629 GYD per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 344 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Jan 10 – 17

G$23,897 GYD per night

Guest favorite

Apartment in Mountain Dale

4.96 out of 5 average rating, 155 reviews

Cute space in Catskills hotspot Mountain Dale

Super cute apartment above the popular Creek Bar restaurant, featured in the NY Post as one of the top outdoor dining destinations in NY State. Enjoy the outdoor Creek Bar in the woods behind this stylish space. The restaurant is currently open Wednesday - Sunday (check insta) Mountaindale is one of the Catskills most hip destinations. Check out other food spots like The Dale craft pizza, Forage and Gather organic market, and shops Great Eye Vintage, Bad Grandma and yoga across the street

Sep 25 – Oct 2

G$30,463 GYD per night

Guest favorite

Apartment in Ellenville

5.0 out of 5 average rating, 11 reviews

Cottage in Catskills, Escape to Nature

Ellenville is an urban village that blends the beauty of nature all around with the energy of a people and place. The cottage is adjacent to the main house in Ellenville, and it is centrally located near restaurants, Cohen's Bakery, The Shadowland Theater, are all within walking distance. If staying in, you can eat under the stars, sip wine on the patio, enjoy the garden or go for a stroll in the village. Otherwise, you are one hour away from everything that the Catskills have to offer.

Jun 22 – 29

G$28,934 GYD per night

Guest favorite

Cottage in Kerhonkson

4.94 out of 5 average rating, 255 reviews

Blue Haven in the Catskills

We built a studio-house on the foundation of an old summer cottage. We did not expand the footprint, but furnished it with select pieces and appliances and gave it contemporary finishes. We also added a screened porch, open deck and stone patio. The woodland and mountain views are lovely, while the location is convenient to Lake Minnewaska State Park and the Mohonk Preserve. Ulster County levies a 2% tax on overnight stays. Payment is made anytime between confirmation and arrival.

Sep 30 – Oct 7

G$22,121 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 740 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 4 – 11

G$22,968 GYD per night