Holiday Homes in Craryville

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Find holiday rentals that suit your style

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Cabins
Cabins
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Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Craryville holiday homes

An outdoor seating area with wicker furniture and a view of a forested landscape.

1. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Hillsdale
The price is AU$2,165
includes taxes & fees
25 Nov - 26 Nov
Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
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, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AU$195
includes taxes & fees
19 Nov - 20 Nov
All the comforts of home
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

3. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AU$903
includes taxes & fees
14 Nov - 15 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A covered pool area with a small gazebo, a shed, and a lounge chair.

4. Charming Hudson Valley Escape | Autumn Vibes & Fire Pit

Charming Hudson Valley Escape | Autumn Vibes & Fire Pit
Claverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
United States
jessica c.
Charming Hudson Valley Escape | Autumn Vibes & Fire Pit
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. 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 AU$439
includes taxes & fees
13 Dec - 14 Dec
Home in Great Barrington
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.

6. 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 AU$646
includes taxes & fees
18 Nov - 19 Nov
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A camping setup with a metal chair and a table by a river in a forest.

7. 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, (18 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 AU$477
includes taxes & fees
22 Nov - 23 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

8. 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 AU$586
includes taxes & fees
24 Nov - 25 Nov
Cheerful 3-bedroom cottage with woodstove
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

9. 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)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is AU$426
includes taxes & fees
14 Nov - 15 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A dining area with a wooden table, chairs, and a ceiling fan.

10. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
Great Barrington
9.6 out of 10, Exceptional, (29 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 AU$438
includes taxes & fees
16 Nov - 17 Nov
A Cozy Berkshire Escape l Close to the Slopes
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

11. Modern cabin retreat

Modern cabin retreat
Catskill
The price is AU$373
includes taxes & fees
16 Nov - 17 Nov
Modern cabin retreat
A modern living space with a kitchen area, a dining table, and a sofa.

12. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is AU$389
includes taxes & fees
16 Nov - 17 Nov
Cabin Oasis near Town
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.

13. 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, (10 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 AU$1,752
includes taxes & fees
20 Nov - 21 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A kitchen with a central island, bar stools, and pendant lighting.

14. 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 AU$372
includes taxes & fees
6 Dec - 7 Dec
Cozy Catskill Escape
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AU$987
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden deck with a wicker sofa, a hammock, and a grill.

16. Modern Family Home · Walk to Lake · Firepit

Modern Family Home · Walk to Lake · Firepit
Athens
10.0 out of 10, Exceptional, (2 reviews)
"Lovely home with reasonable accessibility. Host was very responsive. Clean and quiet. Beautiful scenery."
United States
Kellie H.
The price is AU$797
includes taxes & fees
15 Nov - 16 Nov
Modern Family Home · Walk to Lake · Firepit
Cook, gather, and connect with a central island

17. 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 AU$1,076
includes taxes & fees
15 Nov - 16 Nov
Catskill, Screened Porch, Chef’s Kitchen
A couple in a hot tub with a natural landscape in the background.

18. Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson

Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is AU$528
includes taxes & fees
15 Nov - 16 Nov
Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

19. 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 AU$1,070
includes taxes & fees
16 Nov - 17 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

20. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (36 reviews)
"Fantastic place way better than expected."
United States
Robert H.
The price is AU$422
includes taxes & fees
3 Dec - 4 Dec
Catskill Cottage Walk to Downtown & River Views
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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Learn more about Craryville

Escape to Craryville! Enjoy its wildlife and dining.

See all hotels in Craryville
A misty forest landscape with a hill in the background.

Top reviews in Craryville

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville

10/10 Excellent

Great to stay here with real people and eat good home cooked food after nights in dreary lookalike chain hotels
Australia
Anonymous traveller
Reviewed September 22, 2019
Changing Times Boutique Country Lodging