A misty forest landscape with a hill in the background.

Holiday Homes in Craryville

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Craryville holiday homes

A wooden deck with a staircase leading to a covered porch area.

1. 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 NZ$247
includes taxes & fees
22 Sept - 23 Sept
All the comforts of home
A two-story house with a balcony, a deck, and a view of the surrounding forest.

2. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (133 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 NZ$1,245
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

3. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (29 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is NZ$313
includes taxes & fees
28 Sept - 29 Sept
Catskill Cottage Walk to Downtown & River Views
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

4. 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 NZ$582
includes taxes & fees
24 Sept - 25 Sept
Home in Great Barrington
A camping setup with a metal chair and a table by a river in a forest.

5. 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 NZ$585
includes taxes & fees
22 Sept - 23 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A kitchen with a central island, bar stools, and pendant lighting.

6. 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 NZ$462
includes taxes & fees
28 Sept - 29 Sept
Cozy Catskill Escape
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

7. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 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 NZ$548
includes taxes & fees
22 Sept - 23 Sept
Riverside Retreat in the Berkshires
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

8. Modern cabin retreat

Modern cabin retreat
Catskill
The price is NZ$471
includes taxes & fees
28 Sept - 29 Sept
Modern cabin retreat
A modern living space with a kitchen area, a dining table, and a sofa.

9. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is NZ$500
includes taxes & fees
29 Sept - 30 Sept
Cabin Oasis near Town
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

10. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$770
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

11. 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 NZ$1,090
includes taxes & fees
22 Sept - 23 Sept
Chic Barn Style * Fireplace * Near Stissing House
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.

12. 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 NZ$833
includes taxes & fees
14 Oct - 15 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

13. 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 NZ$1,243
includes taxes & fees
29 Sept - 30 Sept
Catskill * Screened Porch * Chef’s Kitchen
A wooden deck with a wicker sofa, a hammock, and a grill.

14. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
10.0 out of 10, Exceptional, (1 review)
"Great property, very nice and updated, also good location at the lake"
United States
Dan K.
The price is NZ$960
includes taxes & fees
22 Sept - 23 Sept
Larkspire I Sleepy Hollow Lake I Beach & Firepit
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

15. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is NZ$1,298
includes taxes & fees
22 Sept - 23 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A modern building with a wooden deck and a door.

16. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is NZ$941
includes taxes & fees
22 Sept - 23 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A cabin with a large deck, multiple windows, and a fire pit.

17. 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 NZ$591
includes taxes & fees
24 Sept - 25 Sept
Modern Luxurious Cabin, Catskills - The Tiny Nook
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.

18. 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, (7 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 NZ$2,244
includes taxes & fees
23 Sept - 24 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

19. 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 NZ$1,243
includes taxes & fees
23 Sept - 24 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 7 hours ago
The Red Lion Inn

Find out more about Craryville

Craryville Holiday Homes information

Number of reviews
3,897
Accommodation
622 Holiday Homes
Lowest Price
NZ$146
Highest Price
NZ$700