Craryville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Craryville vacation rentals

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (195 reviews)
"Great stay"
United States
George
The price is CA $138
CA $155 total
includes taxes & fees
Nov 9 - Nov 10
Micosta Leisure Inn
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

2. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is CA $248
CA $289 total
includes taxes & fees
Nov 9 - Nov 10
The Brooks Motel: Exceptional Suite
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

3. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (340 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is CA $213
CA $291 total
includes taxes & fees
Dec 7 - Dec 8
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A wooden deck with a staircase leading to a covered porch area.

4. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is CA $138
CA $173 total
includes taxes & fees
Nov 9 - Nov 10
All comforts of home
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

5. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is CA $245
CA $487 total
includes taxes & fees
Nov 9 - Nov 10
Ideal location for summer and winter activities with plenty of outdoor space.
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

6. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is CA $107
CA $162 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 1-bedroom studio in serene Great Barrington with AC
A wooden deck with a staircase leading to a covered porch area.

7. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is CA $149
CA $186 total
includes taxes & fees
Nov 8 - Nov 9
All the comforts of home
A compact kitchen with a microwave, coffee maker, and sink. There is a small dining area with two orange chairs and a table.

8. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is CA $248
CA $297 total
includes taxes & fees
Nov 9 - Nov 10
The Brooks Motel: Exceptional Suite
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

9. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is CA $279
CA $510 total
includes taxes & fees
Nov 9 - Nov 10
Hudson NY’S Country Serenity Guest Suite.
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

10. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
10.0 out of 10, Exceptional, (1 review)
"Amazing sauna session"
United States
AYANO
The price is CA $312
CA $381 total
includes taxes & fees
Nov 8 - Nov 9
Gatherwild Ranch
A kitchen with white cabinetry, granite countertops, and a window with blinds.

11. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is CA $170
CA $341 total
includes taxes & fees
Nov 16 - Nov 17
Charming loft cottage in tranquil Germantown with WiFi, AC
A backyard with a fire pit, wooden deck, and string lights.

12. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is CA $262
CA $490 total
includes taxes & fees
Nov 9 - Nov 10
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A sandy beach with a lake and forest in the background.

13. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is CA $293
CA $456 total
includes taxes & fees
Nov 9 - Nov 10
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden cabinet with multiple drawers, a tray with decorative items, and a variety of glassware and bottles.

14. Sky view retreat, a serene hillside hideaway

Sky view retreat, a serene hillside hideaway
Hudson
The price is CA $296
CA $532 total
includes taxes & fees
Nov 9 - Nov 10
Sky view retreat, a serene hillside hideaway
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

15. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is CA $303
CA $452 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is CA $195
CA $355 total
includes taxes & fees
Nov 29 - Nov 30
Modern cabin retreat
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

17. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is CA $280
CA $602 total
includes taxes & fees
Nov 8 - Nov 9
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A restaurant with outdoor seating, a sign for 'The New York Restaurant', and a nearby antique shop.

18. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is CA $252
CA $477 total
includes taxes & fees
Nov 9 - Nov 10
Charming Cottage in the Heart of Catskill & Pet Friendly
A modern living space with a kitchen area, a dining table, and a sofa.

19. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is CA $195
CA $371 total
includes taxes & fees
Nov 16 - Nov 17
Cabin Oasis near Town
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $249
CA $574 total
includes taxes & fees
Nov 18 - Nov 19
Cheerful 3-bedroom cottage with woodstove
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

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington

10/10 Excellent

Excellent room! Clean and good breakfast!
Canada
Kelly
Reviewed October 10, 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, 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 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 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 Craryville 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 Craryville vacation rentals we have selected for you start as low as CA $107 per night. Entering your travel dates in the search wizard 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.

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?

Modern Luxurious Cabin, Catskills - The Tiny Nook: You might want to consider this vacation rental near Craryville, which is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.