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

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

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
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Eating area leading to one pristeen acre looking out to waterfront

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AED 665
AED 1,342 total
includes taxes & fees
1 Jan - 2 January 2025
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Exterior

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 1,080
AED 1,975 total
includes taxes & fees
7 Jan - 8 January 2025
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft

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!
The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds
Aerial view

The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

2.0 star property
The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds
Trails Head Tiny House
Updated picture of the exterior with the extended deck.

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AED 290
AED 455 total
includes taxes & fees
22 Dec - 23 Dec
Trails Head Tiny House
NEW LISTING! Cozy Country Farmhouse with Hot Tub
Exterior

NEW LISTING! Cozy Country Farmhouse with Hot Tub

9.4 out of 10, Exceptional, (3)
"Perfect property for a quiet weekend. Dogs had plenty of room to run free"
NEW LISTING! Cozy Country Farmhouse with Hot Tub
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!
Living area

Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!

10.0 out of 10, Exceptional, (9)
"The property is sensational. The house has everything that you would need for enjoyment of all ages. My forty year old son said this place is “Sick”. Sick meaning absolutely awesome! Great property to rent for a large family or several couples weekend. "
The price is AED 2,039
AED 3,482 total
includes taxes & fees
8 Jan - 9 January 2025
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!
Catskill dreamy pet friendly country house for a unique getaway experience.
The Tannery House

Catskill dreamy pet friendly country house for a unique getaway experience.

9.8 out of 10, Exceptional, (7)
"We loved the comfortness and homeyness of the house. We loved the fact that the backyard is fenced in. Our dogs loved it. It was also great that it was dog friendly, they have a dog bed and feeding station. The 🏡 stress is great and very caring."
Catskill dreamy pet friendly country house for a unique getaway experience.
Serene escape with private lake

Serene escape with private lake

10.0 out of 10, Exceptional, (3)
"12 men fir hold and relax "
The price is AED 2,997
AED 5,502 total
includes taxes & fees
2 Jan - 3 January 2025
Serene escape with private lake
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Terrace/patio

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

10.0 out of 10, Exceptional, (22)
"Let me start off by saying Bernadette is a very attentive host, communication was great despite the fact that she was dealing with a family emergency during our trip. The location is exactly what my friends and I were after - an escape with no neighbors in sight, a place where we could cook, play cards, and gaze at the stars with minimal light pollution. All the amenities promised were there, all the utilities worked as expected, and the view was phenomenal. Be aware that the home has some...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
The Studio at the Inn at High Falls
Exterior

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 Studio at the Inn at High Falls
Secluded Family Haven ~ Yard ~ GameRoom ~ Fire Pit
Exterior

Secluded Family Haven ~ Yard ~ GameRoom ~ Fire Pit

7.6 out of 10, Good, (14)
"We had a great time for our family getaway. The house was sized for a summer getaway with a large family/group. Plenty of bedrooms and bathrooms and even a second fridge to accommodate our needs. When the game room is available, the house will be even better"
Secluded Family Haven ~ Yard ~ GameRoom ~ Fire Pit
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Welcome to the Louie II. A serene setting for your next Hudson Valley getaway.

The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard

9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Beautiful Private Stone Home in the Hudson Valley
Exterior

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

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

10.0 out of 10, Exceptional, (117)
"The home is nestled in the woods and surrounded by amazing boulders . The mid century home is comfortable and stunning . We stayed at the house for a quiet weekend visiting friends in the area. The home is well equipped and a joy to stay and relax in . The area is a hikers dream and there are many amazing places to explore . The working fireplace adds a magical atmosphere. We hope to visit this property again . "
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
The Loft At The Inn At High Falls
Exterior

The Loft At The Inn At High Falls

8.6 out of 10, Excellent, (10)
"Frank's place had everything we needed for the perfect end to summer weekend. He was responsive and his instructions were easy. We hope to come back someday!"
The Loft At The Inn At High Falls
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Interior

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
Sweet and spacious mountain view home w/fireplace!
Living area

Sweet and spacious mountain view home w/fireplace!

9.8 out of 10, Exceptional, (18)
"Loved the layout and the amount of natural light"
Sweet and spacious mountain view home w/fireplace!
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

Huge house with amazing kitchen, near great hiking; great for groups!
From the front of the house.

Huge house with amazing kitchen, near great hiking; great for groups!

10.0 out of 10, Exceptional, (44)
"Northeastern's annual Alternative Weekend trips had an amazing stay over Veteran's Day weekend! The group volunteered with the local Woodstock Animal Sanctuary. Students and staff raved about the house!"
Huge house with amazing kitchen, near great hiking; great for groups!
Fabulous cozy farmhouse on a Hudson Valley mountaintop
Exterior

Fabulous cozy farmhouse on a Hudson Valley mountaintop

10.0 out of 10, Exceptional, (32)
"House and neighborhood were perfect."
Fabulous cozy farmhouse on a Hudson Valley mountaintop
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
Welcome to the Claryville Cabin!

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

10.0 out of 10, Exceptional, (204)
"Very comfortab;e and cozy"
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
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.