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Compare 364 Vacation Homes in Cragsmoor with updated reviews, rates, and availability.

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (36)
"Needed rest and quiet away from the city! Not only was this the perfect location, but William is a fantastic host. Great communication before and after, from directions to access and operation with kindness and generosity of spirit. Will return! "
Red Barn Retreat - Shawangunk Mountains Getaway

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is AED 1,010
AED 1,200 total
includes taxes & fees
28 Mar - 29 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Beaver Lake Escape

9.4 out of 10, Exceptional, (15)
"Greatly enjoyed our short stay. The dog bones were a nice touch for our pups. Extremely clean, great layout - we would love to return soon"
The price is AED 606
AED 928 total
includes taxes & fees
31 Mar - 1 Apr
Beaver Lake Escape

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (76)
"We had a perfect stay at the beautiful farmhouse with all of the modern amenities.Outdoor space is to die for fenced in for your pup walking trails nature trails water features running streams..Cherry on top is that the listing is very generous with check-in and checkout times you can check in at 3 and you check out at 12. This feature allows for true relaxation!Book it!!"
Modern Farmhouse on pristine private 12 Acres

Dream House in the Gunks

10.0 out of 10, Exceptional, (24)
"Awesome place, great location. We loved our stay."
The price is AED 301
AED 688 total
includes taxes & fees
3 Apr - 4 Apr
Dream House in the Gunks

Cozy Rustic Farmhouse With Wood Stove

Cozy Rustic Farmhouse With Wood Stove

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

8.0 out of 10, Very Good, (20)
"Nothing negative to say really. Booked this house for 20 guests and it fit us all comfortably. Everything was clean and loved the way this house was layed out. Lots of room and many things to do even inside the house. Huge backyard. Host was very kind. Not many things like paper towel, toilet paper, garbage bags for 4 days with 20 guests as well as no washer and dryer as it’s listed."
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is AED 459
AED 935 total
includes taxes & fees
28 Mar - 29 Mar
The Studio at the Inn at High Falls

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AED 847
AED 1,430 total
includes taxes & fees
3 Apr - 4 Apr
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (30)
"Everything was good and we all enjoyed our stay"
The price is AED 1,392
AED 2,367 total
includes taxes & fees
30 Mar - 31 Mar
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

10.0 out of 10, Exceptional, (121)
"Awesome location if you’re looking to explore around “the gunks”.Minutes from Mohong, Minnewaska, restaurants and grocery store.Host Sascha is responsive and accommodating Definitely recommend if you are looking for a nice quiet place that is private yet close to everything."
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks

9.8 out of 10, Exceptional, (83)
"This place was fantastic and comfortable for our group of (adult) students who were attending a program locally in Cragsmoor. Diane had thorough instructions for everything in the house--the only hiccup was the checkin (somehow we never received the door code) but Diane was responsive on the phone and helped us right away. "
Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks

Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Ample space for food prep and cooking (multiple ovens). Ample space for dining. Comfortable beds. Great lighting. Some reviews claimed there were too many rules, but I didn't find that to be the case. only discrepancy I found was the posting indicated a full-size bed in the game room and a twin bed with trundle in a separate bedroom. It was actually the other way around. This actually worked out better for me :) The only downsides were 1) the doorbell - it worked from the outside but inside the...
Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

The Perfect up to date Private Getaway to call home for a while

8.6 out of 10, Excellent, (4)
"This property and listing was perfect for our men's retreat weekend getaway. We gathered together and enjoyed being able to spread out in the spacious home. It was very close to a local park with a pool, basketball court, and open field. We also enjoyed grilling on the patio and using the fire-pit to roast s'mores in the evening. The driveway had plenty of parking. The pool on the property was unusable but the backyard was perfect for us to play football and have outdoor activities. We...
The Perfect up to date Private Getaway to call home for a while

Waterfront Wallkill Duplex Home w/ Fire Pits!

10.0 out of 10, Exceptional, (22)
"Wonderful host! So helpful and close to everything. The backyard is beautiful to sit and watch the water. "
Waterfront Wallkill Duplex Home w/ Fire Pits!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cragsmoor

Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks

9.8 out of 10, Exceptional, (83)
"This place was fantastic and comfortable for our group of (adult) students who were attending a program locally in Cragsmoor. Diane had thorough instructions for everything in the house--the only hiccup was the checkin (somehow we never received the door code) but Diane was responsive on the phone and helped us right away. "
Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Mountain View escape

10.0 out of 10, Exceptional, (49)
"We had a lovely weekend staying at MVE. The host was communicative and thoughtful and the home was beautiful and clean upon arrival. We look forward to coming back soon! "
Mountain View escape
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.