Cragsmoor Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Cragsmoor

"This place was incredible! It's cozy, clean, and had a great historic feel. We hosted a group of adult students for a program nearby and this was a great place for them to unwind after a day of class and get to know each other, while also having independent space. Jeff was so helpful and available to answer any questions as they arose. He was flexible and friendly; the kitchen was stocked. We definitely hope to return!"

"Another lovely stay! It was a winter wonderland at the cabin this time. Can't wait to come back again!"

"The whole family had a great time! We would love to come back!"

"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "

CA $568 total

includes taxes & fees

Mar 10 - Mar 11

"We had a wonderful stay! The property managers were wonderful. We stayed the night for a birthday celebration and they made the experience extra special. Will definitely return!"

CA $291 total

includes taxes & fees

Feb 18 - Feb 19

"Our stay was great! Host was great at communicating. Enough towels were supplied. Beds were very comfortable. Highly recommended!"

"very old , small, unfinished house . with 26 people as listed you would not have space to walk in the house . Unfortunately due to weather we couldn’t even stand out in backyard , so was pretty congested living for us. This house is more for campers, bachelor groups rather than family . Negatives- 1. No seatings in the house - all together you will have 1 small Futon sofa to seat in the house . Rest need to bring plastic chairs from basement. 2. Unfinished flooring - Flooring in both properties...

"Nothing negative to say really. Booked this house for 20 guests and it fit us all comfortably. Everything was clean and loved the way this house was layed out. Lots of room and many things to do even inside the house. Huge backyard. Host was very kind. Not many things like paper towel, toilet paper, garbage bags for 4 days with 20 guests as well as no washer and dryer as it’s listed."

45-inch Smart TV with cable channels, TV, fireplace

"The property is beautiful. The soft snow blanketing the area only made it more so. Everything was exactly where it was said to be and our hosts were ready and willing to help at a moments notice. Couldn't ask for a better place"

"House is spacious and clean. The little touches like the Christmas decorations, games, books etc. were greatly appreciated. Beautiful property. Would definitely return. "

"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 "

"This property was spectacular. Immaculately clean and every detail done well. From a fully stocked and ready to go kitchen, to comfortable beds, sheets and towels. I’ll be back to stay here again and the host Michelle couldn’t have done more. Having had a few disappointing stays in other properties of late, this was a welcome game changer!!!"

8 bedrooms, iron/ironing board, travel crib, WiFi

"I found this house to celebrate my spouses 40th birthday and it couldn’t have been more perfect. In total we had 17 people and the house was more than enough for all of us. All the couples had their own room (4 couples) and everyone else had a bed with room to spare. Everything was clean and dealing with the owners and property manager was Hassle free and they available to us with anything we needed which was great! Everything from the inside to the outside of the house just made our stay that...

CA $2,089 total

includes taxes & fees

Feb 13 - Feb 14

"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."

"We were a group of 3 families , adults and kids age range 2-12yr olds for a long. New Year’s Eve getaway. Peter was very responsive the entire stay for any questions we had. The place was just as listed and very clean upon arrival. We had enough room and beds for everyone to sleep comfortably. We used the fireplace nightly and the kids enjoyed running around outside when it wasn’t raining. The kids loved having their own bunk bed room away from the adults. The cabin was about 20 mins from...

"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...

CA $365 total

includes taxes & fees

Feb 13 - Feb 14

"We had a wonderful stay in this quiet gem. Clean, comfortable, cute, and cozy. Highly recommended! "

"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "

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"Kids had a great time for my daughters 9th bday I stayed in the hot tub most of the time we are looking to coming during the spring "

CA $399 total

includes taxes & fees

Feb 27 - Feb 28

"-"

CA $348 total

includes taxes & fees

Feb 24 - Feb 25

"Overall great service "

CA $152 total

includes taxes & fees

Feb 23 - Feb 24

Find out more about Cragsmoor

Everything you need to know about Cragsmoor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cragsmoor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cragsmoor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cragsmoor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cragsmoor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cragsmoor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cragsmoor vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cragsmoor rentals

At Expedia, we put the best Cragsmoor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cragsmoor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cragsmoor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cragsmoor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Cragsmoor Vacation Rental Travel Info

Number of vacation rentals	3
Popular accommodation	Cragsmoor private vacation homes
Known landmarks	Lake Minnewaska Beach, Stony Kill Falls and VerKeerderkill Falls
International airports	New York, NY (JFK-John F. Kennedy Intl.), Newark, NJ (EWR-Liberty Intl.) and New York, NY (LGA-LaGuardia)

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Frequently asked questions

Can I find vacation rentals in Cragsmoor?

Yes, you can find vacation rentals close to popular points of interest in Cragsmoor, or you can choose a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Cragsmoor?

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!: This vacation home rental outside Cragsmoor is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Cragsmoor?

With 11 Expedia vacation rentals, you're sure 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 larger area, you’ll find Shawangunk Ridge State Forest and Lake Minnewaska Beach.

What are vacation rentals like in Cragsmoor?

Vacation rentals are private properties you can reserve for several days or longer in Cragsmoor. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.

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Cragsmoor Vacation Rentals

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Vacation Rentals in Cragsmoor

Fabulous cozy farmhouse on a Hudson Valley mountaintop

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Trails Head Cabin

Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski

Spacious Getaway! 7BR w Park & pool Scenic Views

The Highland: Private Country Cottages, Pool, GameRoom 30+ beds

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Dome House Retreat

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Catskills mountain gateway house.

Mountain View escape

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

Serene escape with private lake

Beautiful Private Stone Home in the Hudson Valley

Log Cabin in Catskill NYS

The Studio at the Inn at High Falls

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

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

Other types of properties in Cragsmoor you may be interested in

The Kartrite Resort & Indoor Waterpark

Resorts World Catskills Casino

Courtyard by Marriott Middletown Goshen

Find out more about Cragsmoor

Cragsmoor Vacation Rental Travel Info

Explore a world of travel with Expedia

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Frequently asked questions