Craryville Vacation Rentals

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In two weeks
Dec 26 - Dec 28
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Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Craryville vacation rentals

Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

3.0 star property
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$133 nightly
The price is $150
Dec 19 - Dec 20
Total with taxes and fees
Micosta Leisure Inn
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Cabin in Saugerties

8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Dec 10 - Dec 11
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Apartment in Saugerties

9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Terrace/patio
Hamptons on the Hudson in South Saugerties

Vacation Home in Glasco

10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Cabin in Saugerties

9.0 out of 10, Wonderful, (13)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
$307 nightly
The price is $332
Dec 10 - Dec 11
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Dec 16 - Dec 17
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Vacation Home in Coxsackie

10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
1 bedroom, desk, free WiFi
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Apartment in Red Hook

9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
$195 nightly
The price is $221
Dec 10 - Dec 11
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Exterior
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Vacation Home in Old Chatham

9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Outdoor dining
Charming 2-bedroom Waterfront home with boat access in Saugerties

Vacation Home in Saugerties

9.4 out of 10, Exceptional, (9)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
$440 nightly
The price is $492
Dec 10 - Dec 11
Total with taxes and fees
Charming 2-bedroom Waterfront home with boat access in Saugerties
Property grounds
Private Yacht on Catskill Creek

Houseboat in Catskill

9.8 out of 10, Exceptional, (28)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
United States
Jay
Private Yacht on Catskill Creek
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Exterior
Sioux Tipi on Chloe's Lake

Vacation Home in Saugerties

9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
Sioux Tipi on Chloe's Lake
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook

Vacation Home in Catskill

10.0 out of 10, Exceptional, (7)
"Great place. Exactly like the pictures. "
United States
robert a.
$319 nightly
The price is $345
Dec 10 - Dec 11
Total with taxes and fees
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Saugerties

10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
$171 nightly
The price is $192
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
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 Craryville Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Craryville

Everything you need to know about Craryville 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 Craryville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Craryville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Craryville vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Craryville rentals

At Expedia, we put the best Craryville 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 Craryville 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 Craryville 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 Craryville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Craryville?

Yes, we have vacation rentals near the most popular sights in Craryville, or you can select a more secluded option if you're looking for relaxation. Craryville is known for its restaurants.

What's the top vacation rental in Craryville?

Pet Friendly Riverfront Home in Great Barrington: Visitors like this Craryville vacation home rental. It is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Craryville?

Expedia has 22 vacation rentals for your stay in Craryville.

What’s there to see and do in Craryville?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Copake Lake. Catamount Aerial Adventure Park and Catamount Ski Area are a couple of places you'll find in the larger area.

What’s a vacation rental in Craryville like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Craryville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.