Search Cottages in Cragsmoor

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 65 Cottages in Cragsmoor with updated reviews, rates, and availability.

Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (44)
"Charming. Peaceful. Beautiful. Well-designed. Well-stocked. I cannot recommend this place enough. It is the ideal getaway for an individual or couple. Hope to have a reason to return soon! "
Mountain View escape
Quaint village, walk to restaurants and shops.
Exterior detail

Quaint village, walk to restaurants and shops.

9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.
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
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
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 1,144 total
includes taxes & fees
20 Dec - 21 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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 249
AED 601 total
includes taxes & fees
8 Jan - 9 January 2025
Dream Cottage in the Gunks
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 Dec - 21 Dec
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
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.
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, (7)
"The whimsical cottage was very cute and comfortable. It was clean to the naked eye, however there were cobwebs in the windowsill behind the sofa. I wanted to go sit on the Adirondack chairs behind the house it those have not been wiped down at all. The shower is very small and dark. I realize it is an amenity to have its and pans however they definitely can be updated, it is hard to cook anything on an uneven pan. Overall it was a nice stay"
Whimsical Woodland Cottage in Stone Ridge NY
Leggett Cottage, High Falls, NY.

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (69)
"Lovely property in great location. Easy to explore Catskills and Hudson Valley. Amenities close by. "
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"
The price is AED 595
AED 1,028 total
includes taxes & fees
20 Dec - 21 Dec
Cozy Haven: A Romantic Retreat in our Tiny House!
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
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
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 1,120 total
includes taxes & fees
2 Jan - 3 January 2025
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 2,189 total
includes taxes & fees
19 Jan - 20 January 2025
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!
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.
Don't see what you're looking for?
See all available properties in Cragsmoor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.

Frequently asked questions

Why book your cottage in Cragsmoor with Expedia?
Reserving a cottage in Cragsmoor is as simple as deciding on your travel dates and choosing your ideal place for a getaway in the outdoors. From high-end retreats to low-cost properties and cottages that come with conveniences like a kitchen, Expedia has something for all traveler tastes. As for the best offers around? We’ve got them too!
How can I find cheap cottages in Cragsmoor?
A wonderful way to uncover cheap cottages in Cragsmoor is with Expedia’s handy filter tool. Tailor your search results by amenities, star rating and budget to take advantage of unbeatable bargains in just a few clicks.