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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Compare 64 Cottages in Cragsmoor with updated reviews, rates, and availability.

Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Private kitchen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (9)
"We had a great stay in this cozy cabin! The beds were comfortable and the views of the farm and deer were beautiful ! Communication with Ginny was quick and she let us adjust our dates of stay when needed. 😊"
The price is AED 606
AED 1,147 total
includes taxes & fees
20 Jan - 21 Jan
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Summer at the Lily

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (27)
"We had a wonderful stay in this quiet gem. Clean, comfortable, cute, and cozy. Highly recommended! "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Living area

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

10.0 out of 10, Exceptional, (6)
"We had a fabulous stay at Judy's place. The beds were very comfortable, and the location was good. When we had an issue with the furnace, the owner went out of her way to correct the problem and ensured that we were comfortable. We would recommend this place."
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Stony Kill Ranch - Bohemian Paradise on Minnewaska

Stony Kill Ranch - Bohemian Paradise on Minnewaska

7.4 out of 10, Good, (3)
"Some friends and our pups were looking to spend a nice weekend upstate with our dogs to relax and spend time, and this place was perfect. The location is GREAT! It is near hiking trails, some breweries/orchards and while we didn’t go to dinner, there were restaurants around as well. The house was as described, spacious and had a lot to offer. We loved spending time in the hot tub and around the fire pit. The jam shed was a lot of fun for some in our group too! Check in was easy and when we had a...
Stony Kill Ranch - Bohemian Paradise on Minnewaska
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Hand-hewn beams & cathedral ceilings

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

9.8 out of 10, Exceptional, (52)
"Very beautiful property! Beautiful night sky views and excellent nature, perfect place for a romantic weekend"
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Cozy Cottage with a Pond 2
Property grounds

Cozy Cottage with a Pond 2

6.0 out of 10, (12)
"I don't like to put negative energy out into the Universe BUT... from the steep slippery stairs to the upside down entry door to the lack of water- no water at all in the morning- then the sulfuric water. And then there was the creepy cat picture on the wall. We named the place the S King Lodge after our favorite horror writer. The stairs alone are a red red flag. No light at the top of these steep, jankily constructed danger. And then theres the inside for which the only word that suits the...
The price is AED 367
AED 477 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Cottage with a Pond 2
Cozy Cottage with a Pond
Property grounds

Cozy Cottage with a Pond

10.0 out of 10, Exceptional, (1)
"My husband and I enjoyed two nights in this quiet and cozy cottage. I LOVED spending time on the porch looking out onto the beautiful pond and watching the stars at night. This was a perfect getaway and break from the busy world and look forward to future trips here again."
Cozy Cottage with a Pond
Whimsical Woodland Cottage in Stone Ridge NY
Curl up on this plush, gorgeous leather couch next to a picture perfect fire.

Whimsical Woodland Cottage in Stone Ridge NY

9.8 out of 10, Exceptional, (8)
"Whimsical cottage was just as described. The owner was very responsive with any questions. The location was perfect for our needs. It is definitely meant for a couples weekend away, but was sufficient for the three of us."
Whimsical Woodland Cottage in Stone Ridge NY
Leggett Cottage, High Falls, NY.

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (69)
"Very comfortable, relaxing and clean. Great space. Will be back Thank you very much - Patricia"
Leggett Cottage, High Falls, NY.
Charming Lakefront Cottage On Masten lake
Outdoor dining

Charming Lakefront Cottage On Masten lake

9.8 out of 10, Exceptional, (34)
"We really enjoyed this cozy little college next to the lake. It was a perfect place to stay when going to multiple nights of concerts at Bethel Woods. We would love to return some time. The owner is kind and communicative and the entire process was very stress free. Great little place for a couple."
Charming Lakefront Cottage On Masten lake
Cozy Haven: A Romantic Retreat in our Tiny House!
Room

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
Cozy Haven: A Romantic Retreat in our Tiny House!
Dream Cottage in the Gunks
Dream Cottage fireplace is made out of local Gunks' rock by yours truly. It has a propane burner and provides a great source of heat during winter. The fireplace is controlled by the thermostat that is located on the left side of the bedroom entry

Dream Cottage in the Gunks

9.6 out of 10, Exceptional, (7)
"Perfectly situated near recreational spots. Cottage is exactly as advertised. Check in SO EASY! Thank you for the coffee and tea. "
The price is AED 235
AED 587 total
includes taxes & fees
4 Feb - 5 Feb
Dream Cottage in the Gunks
Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway
Exterior

Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway

10.0 out of 10, Exceptional, (1)
"My husband and I spent a few days at Steven’s beautifully decorated historic schoolhouse with our pup, and had a wonderful time, despite the heatwave! Steven is an incredibly responsive host and had a binder full of helpful recommendations for hiking and local food. We will be back!"
Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway
Lakefront Property in the Heart of the Catskills!
Rock Hill Vacation Rental | 2BR | 1BA | 950 Sq Ft | Stairs Required

Lakefront Property in the Heart of the Catskills!

10.0 out of 10, Exceptional, (34)
"This cozy two bedroom one bath lakefront home met all of our needs! Situated at the quiet, less-developed end of Wanaksink Lake, the home features two kayaks, paddles, life jackets, a rowboat, a fire pit, plenty of wood generously provided by the home owner, a wheelbarrow to transport the wood, Adirondack chairs with seat cushions, fishing poles and a tackle box, an outdoor grill, outdoor shower, and a picnic table with umbrella. The kitchen has everything you’ll need except food. There’s a...
Lakefront Property in the Heart of the Catskills!
Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!
Living area

Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!

3.0 star property
Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
The price is AED 661
AED 1,117 total
includes taxes & fees
22 Jan - 23 Jan
Hello Small Stone
Charming Cottage in the Heart of the Shawangunks
Exterior

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (7)
"My bridesmaids and I stayed here the night before my wedding and my husband and I the night of my wedding ..it is absolutely beautiful and private just what we wanted! Would definitely stay here again!"
The price is AED 1,286
AED 2,204 total
includes taxes & fees
20 Jan - 21 Jan
Charming Cottage in the Heart of the Shawangunks
Huguenot Retreat w/ Screened Porch & Lake Access!
Exterior

Huguenot Retreat w/ Screened Porch & Lake Access!

3.0 star property
Huguenot Retreat w/ Screened Porch & Lake Access!
Cozy Campbell Hall Getaway w/ Porch!
Living area

Cozy Campbell Hall Getaway w/ Porch!

3.0 star property
Cozy Campbell Hall Getaway w/ Porch!
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!

9.8 out of 10, Exceptional, (46)
"Second stay. Looking forward to our third. "
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, (33)
"We rang in the new year here with a large group - adults, kids, and dogs - and the house was wonderful. Everything is well stocked and thoughtfully laid out and labeled. “Cozy” here isn’t a real estate euphemism; the decor and overall feel is very warm and comfortable. The kids (ages 5 to 9) had a great time with all of the kids books, movies, and dress up outfits provided. I imagine this experience really shines in the warmer months, but don’t pass up on a winter stay!"
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, (208)
"Very quiet and relaxing.Beautiful surroundings."
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.

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