Book Holiday Homes in Cragsmoor

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Cragsmoor

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

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

Monticello
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and a water park. Our guests praise the property condition in ...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

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

New Paltz
Book a stay at this family-friendly vacation home in New Paltz. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Mohonk Preserve Visitor ...
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
Catskills mountain gateway house.

Catskills mountain gateway house.

Bloomingburg
Stay at this vacation home in Bloomingburg. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Roosa Gap State Forest and Wurtsboro Ridge ...
Catskills mountain gateway house.
Save an average of 15% on thousands of hotels when you're signed in
Red Barn Retreat - Shawangunk Mountains Getaway

Red Barn Retreat - Shawangunk Mountains Getaway

Gardiner
Book a stay at this family-friendly vacation home in Gardiner. Enjoy free WiFi, a garden, and patios. Popular attractions Whitecliff Vineyard and DM Weil Gallery ...
Red Barn Retreat - Shawangunk Mountains Getaway
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Newburgh
The price is NZ$865 per night from 30 Apr to 1 May
NZ$865
includes taxes & fees
30 Apr - 1 May
Book a stay at this family-friendly vacation home in Newburgh. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
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

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

Highland
Book a stay at this family-friendly vacation home in Highland. Enjoy free WiFi, a garden, and a pool table. Popular attractions Apple Greens Golf Course and ...
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Beaver Lake Escape

Beaver Lake Escape

Rock Hill
The price is NZ$454 per night from 28 Apr to 29 Apr
NZ$454
includes taxes & fees
28 Apr - 29 Apr
Stay at this vacation home in Rock Hill. Enjoy an in-room coffeemaker, air conditioning, and a hot tub. Popular attractions Resorts World Catskills and Lake ...
Beaver Lake Escape
Modern Farmhouse on pristine private 12 Acres

Modern Farmhouse on pristine private 12 Acres

Wallkill
Stay at this vacation home in Wallkill. Enjoy free WiFi, a garden, and patios. Popular attractions Whitecliff Vineyard and Lake Awosting Beach are located ...
Modern Farmhouse on pristine private 12 Acres
Dream House in the Gunks

Dream House in the Gunks

Kerhonkson
The price is NZ$311 per night from 28 Apr to 29 Apr
NZ$311
includes taxes & fees
28 Apr - 29 Apr
Stay at this vacation home in Kerhonkson. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Stony Kill Falls and Holy Trinity Ukrainian ...
Dream House in the Gunks
Don't see what you're looking for?
See all available properties in Cragsmoor
View all properties
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.

Cragsmoor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cragsmoor vacation homes are the perfect way for you to wing it.

Holiday houses in Cragsmoor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cragsmoor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cragsmoor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cragsmoor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cragsmoor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cragsmoor Holiday Homes essential information

Accommodation
364 Holiday Homes
Lowest Price
NZ$224
Highest Price
NZ$865
Popular accommodation
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!, Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska, Catskills mountain gateway house., Red Barn Retreat - Shawangunk Mountains Getaway, 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, Beaver Lake Escape , Modern Farmhouse on pristine private 12 Acres, Dream House in the Gunks

Top trending hotels in Cragsmoor

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive, Monticello, NY
The price is NZ$437 per night from 1 May to 2 May
NZ$437
includes taxes & fees
1 May - 2 May
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff ...
The Kartrite Resort & Indoor Waterpark
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is NZ$251 per night from 1 May to 2 May
NZ$251
includes taxes & fees
1 May - 2 May
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 26 May to 27 May
NZ$224
includes taxes & fees
26 May - 27 May
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sleep Inn & Suites Middletown - Goshen
Save an average of 15% on thousands of hotels when you're signed in
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is NZ$387 per night from 29 Apr to 30 Apr
NZ$387
includes taxes & fees
29 Apr - 30 Apr
Stay at this 4.5-star luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
Resorts World Catskills Casino
Don't see what you're looking for?
See all available properties in Cragsmoor
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.