Cragsmoor Holiday Rentals

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Holiday Rentals in Cragsmoor

Fabulous cozy farmhouse on a Hudson Valley mountaintop
10.0 out of 10, Exceptional, (27)
"Loved the house, it was fully stocked. Enjoyed hanging out by the fireplace with family. Cooked with ease, I didn't have to search for any cooking apparatus. When we went out to eat we went to Aroma Thyme Bistro and Gaby's. Jeff communicated really well with me. I would definetley rent again, and don't forget to visit Sam's Point."
Fabulous cozy farmhouse on a Hudson Valley mountaintop
Cottage Suites
3.0 star property
9.0 out of 10, Wonderful, (2)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
The price is NZ$415
includes taxes & fees
18 Jun - 19 Jun
Cottage Suites
Trails Head Tiny House
10.0 out of 10, Exceptional, (5)
"It was great"
The price is NZ$200
includes taxes & fees
12 Jun - 13 Jun
Trails Head Tiny House
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5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
10.0 out of 10, Exceptional, (34)
"Thanks so much for a great stay. This is such a wonderful place for large groups! Nice hikes in the area too, which we took advantage of. Kitchen and bar area was especially good for cooking and eating for 30+ people!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Trails Head Cabin
9.8 out of 10, Exceptional, (57)
"This is a great property we have now stayed multiple times and the property owners make sure everything is perfect on arrival. Will be staying again!"
The price is NZ$314
includes taxes & fees
6 Jun - 7 Jun
Trails Head Cabin
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
10.0 out of 10, Exceptional, (186)
"Another wonderful stay at the Claryville cottage. Quiet, comfortable, relaxing, both inside and outside. Just the perfect weekend."
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
10.0 out of 10, Exceptional, (12)
"We loved all the thoughtful touches and design details of this cozy cabin! P"
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
Cozy Cottage with a Pond 2
6.8 out of 10, (9)
"Safe quiet clean the only thing was the power went out (quick fix though) and the bed was so hard it hurt my back "
The price is NZ$210
includes taxes & fees
7 Jun - 8 Jun
Cozy Cottage with a Pond 2
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Royal Garden Main Cabin
10.0 out of 10, Exceptional, (1)
"Nice little cabin that was very clean. We enjoyed our stay."
Royal Garden Main Cabin
Secluded Family Haven ~ Yard ~ GameRoom ~ Fire Pit
8.0 out of 10, Very good, (9)
"Thanks for hosting our celebration for our kids & friends graduation. So many bedrooms with lots of sleeping capacity! Pretty remote area but nice & private. Kit the ShopRite in Liberty on your way there for provisions. With a few tweaks & improvements would be 5 stars!"
Secluded Family Haven ~ Yard ~ GameRoom ~ Fire Pit
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is NZ$414
includes taxes & fees
10 Jun - 11 Jun
The Studio at the Inn at High Falls
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
9.8 out of 10, Exceptional, (12)
"This property is huge, clean, and gorgeous! me and my wife went for a mini vacation and we were blown away with this place! The host is a great communicator always responding quickly. The grounds are very relaxing, The hot tub is awesome, and the game room in the basement was a great chill. we definitely will be coming back!"
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
Log Cabin in Catskill NYS
10.0 out of 10, Exceptional, (34)
"Was very clean, host was responsive and helpful. We had an issue with the gas and someone came to fix it within 2 hours. It snowed during our stay and the snow was plowed by someone twice. Could only find 2 bathrooms. Not a problem for our group, just informing. Overall, amazing stay and would recommend"
Log Cabin in Catskill NYS
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is NZ$328
includes taxes & fees
11 Jun - 12 Jun
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Cozy Loft Cabin high above Bashakill Wildlife Refuge
9.6 out of 10, Exceptional, (9)
"Nice"
The price is NZ$278
includes taxes & fees
30 Jun - 1 Jul
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is NZ$580
includes taxes & fees
10 Jun - 11 Jun
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Mountain Peak Retreat
8.6 out of 10, Excellent, (4)
"We had a very nice stay at this property. The views were absolutely stunning and the ambience and quiet were just what we were looking for. The outdoor sitting area overlooking the view was outstanding. We had some issues with the lights not working in the main bedroom, trouble using the shower in the main bedroom and that the pool is only heated with additional payment. Despite that we still used the pool and very much enjoyed the hot tub and other amenities that came with the house. Overall...
Mountain Peak Retreat
Quaint village, walk to restaurants and shops.
The price is NZ$493
includes taxes & fees
16 Jun - 17 Jun
Quaint village, walk to restaurants and shops.
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (16)
"We thoroughly enjoyed ourselves at this sweet home, making great use of the spacious yard with the fire pit, the hot tub, and the grill. I kept being amazed at how easy everything was. Every time I needed a utensil, it was wherever I first looked! And when the propane tank emptied in the middle of grilling dinner, I glanced around to see where we might find a full one, and there was one right there waiting. I really appreciated how well thought out and organized everything was. And communication...
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Don't see what you're looking for?
See all available properties in Cragsmoor
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.

Other types of properties in Cragsmoor you may be interested in

The Kartrite Resort & Indoor Waterpark
4.0 star property
8.0 out of 10, Very good, (1024)
"Great place "
The price is NZ$439
includes taxes & fees
6 Jun - 7 Jun
The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino
4.5 star property
8.6 out of 10, Excellent, (1009)
"From the greeting at the Concierge Desk when i checked in.... it wemt all UPHILL!!! Seriously, everyone at the Resort Casino Hotel were so lovely and accomodating. Reservations for dinner, parking was open and easy and breakfast before leaving was so relaxing. It was an experience i would definitely want to REPEAT because of the staff. The people working there MAKE THIS PLACE GREAT"
The price is NZ$377
includes taxes & fees
12 Jun - 13 Jun
Resorts World Catskills Casino
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (393)
"Clean and newer looking. "
The price is NZ$258
includes taxes & fees
16 Jun - 17 Jun
La Quinta Inn & Suites by Wyndham Middletown
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cragsmoor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cragsmoor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cragsmoor. Seeing all the best attractions is bound to make you fall in love with Cragsmoor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cragsmoor short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Cragsmoor?

Yes, there are holiday rentals close to the most popular sights in Cragsmoor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cragsmoor has to offer?

Trails Head Tiny House: This holiday home rental outside of Cragsmoor is situated on a river, and has a BBQ and WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, an electric kettle and kitchenware.

How many holiday rentals will I find in Cragsmoor?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Cragsmoor stay.

What can I see and do in Cragsmoor?

Sam's Point Preserve and Minnewaska State Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Shawangunk Ridge State Forest and Lake Minnewaska Beach.

What are holiday rentals like in Cragsmoor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cragsmoor. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip.

Recent reviews of Cragsmoor properties
Expedia verified reviews