A misty forest landscape with a hill in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Craryville holiday homes

A two-story house with a balcony, a deck, and a view of the surrounding forest.

1. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is £576
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A wooden deck with a staircase leading to a covered porch area.

2. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £110
includes taxes & fees
5 Oct - 6 Oct
All the comforts of home
A two-story house with a front porch, surrounded by lush greenery and trees.

3. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is £606
includes taxes & fees
11 Oct - 12 Oct
Perfect House In Hillsdale, Brings Friends & Fam
A single-story house with a porch, a chimney, and a well-maintained lawn.

4. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is £245
includes taxes & fees
2 Oct - 3 Oct
Country House offers 2 bedrooms and a den, lots of parking.
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

5. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is £242
includes taxes & fees
4 Oct - 5 Oct
Leaf-Peeper Paradise in the Berkshires
A camping setup with a metal chair and a table by a river in a forest.

6. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is £262
includes taxes & fees
5 Oct - 6 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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.

7. 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 £362
includes taxes & fees
14 Oct - 15 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

8. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (31 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is £335
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is £252
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A modern living space with a kitchen area, a dining table, and a sofa.

11. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is £227
includes taxes & fees
7 Oct - 8 Oct
Cabin Oasis near Town
Cook, gather, and connect with a central island

12. Catskill * Screened Porch * Chef’s Kitchen

Catskill * Screened Porch * Chef’s Kitchen
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is £550
includes taxes & fees
6 Oct - 7 Oct
Catskill * Screened Porch * Chef’s Kitchen
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

13. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is £264
includes taxes & fees
28 Oct - 29 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

14. Modern cabin retreat

Modern cabin retreat
Catskill
The price is £215
includes taxes & fees
5 Oct - 6 Oct
Modern cabin retreat
A kitchen with a central island, bar stools, and pendant lighting.

15. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is £210
includes taxes & fees
6 Oct - 7 Oct
Cozy Catskill Escape
A cabin with a large deck, multiple windows, and a fire pit.

16. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is £268
includes taxes & fees
28 Oct - 29 Oct
Modern Luxurious Cabin, Catskills - The Tiny Nook
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

17. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is £559
includes taxes & fees
28 Oct - 29 Oct
Chic Barn Style * Fireplace * Near Stissing House
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

18. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is £529
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern kitchen with a central island, built-in oven, and a brick accent wall.

19. Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren

Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (1 review)
"A gem! Beautifully furnished, comfortable, well-equipped, and a short walk to town - we would return in a heartbeat."
United States
Katherine B.
The price is £668
includes taxes & fees
20 Oct - 21 Oct
Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

20. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (9 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is £996
includes taxes & fees
7 Oct - 8 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."
Ruth 3-night trip
Posted 3 hours ago
The Red Lion Inn

Find out more about Craryville

Craryville Holiday Homes information

Number of reviews
380
Accommodation
645 Holiday Homes
Lowest Price
£110
Highest Price
£996