Search Cragsmoor Cottage Rentals from CA $187

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Cragsmoor cottages

A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

1. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is CA $212
CA $309 total
includes taxes & fees
Nov 11 - Nov 12
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

2. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
The price is CA $188
CA $319 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

3. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is CA $210
CA $399 total
includes taxes & fees
Nov 12 - Nov 13
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

4. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is CA $299
CA $485 total
includes taxes & fees
Nov 11 - Nov 12
Hike & Fish: Outdoor Retreat Near Trails
A rustic cabin with a stone exterior, wooden deck, and a small porch.

5. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is CA $282
CA $634 total
includes taxes & fees
Nov 15 - Nov 16
Hello Small Stone
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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Top reviews in Cragsmoor

A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown

10/10 Excellent

great!
Canada
Sumaya
Reviewed September 9, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Frequently Asked Questions

Why book your cottage in Cragsmoor with Expedia?

Expedia has some terrific cottages in Cragsmoor, so start packing your bags for an unforgettable stay on nature's doorstep. If you have a certain budget, click on how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a pool or a kitchen. We'll help you find the right fit whatever your escape looks like.

How can I find cheap cottages in Cragsmoor?

The quickest way to spot cheap cottages in Cragsmoor is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to discover awesome rates with only a few clicks.

What is there to do in Cragsmoor near my cottage?

If you want to see the sights of Cragsmoor, pay a visit to Sam's Point Preserve. It's a winner among locals and tourists alike.

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