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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Craryville holiday homes

Property grounds

1. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (36 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is HK$833
HK$1,108 total
includes taxes & fees
10 Sept - 11 Sept
All the comforts of home
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is HK$3,165
HK$5,310 total
includes taxes & fees
9 Sept - 10 Sept
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Interior

3. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (24 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,499
HK$2,367 total
includes taxes & fees
22 Sept - 23 Sept
Riverside Retreat in the Berkshires
Coffee/tea maker, fridge, microwave, oven

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$1,496
HK$2,415 total
includes taxes & fees
15 Sept - 16 Sept
Home in Great Barrington
Exterior

5. Modern cabin retreat

Modern cabin retreat
Catskill
The price is HK$1,035
HK$2,026 total
includes taxes & fees
9 Sept - 10 Sept
Modern cabin retreat
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 HK$1,372
HK$2,504 total
includes taxes & fees
10 Sept - 11 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, oven, stovetop, dishwasher

7. 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 HK$956
HK$2,063 total
includes taxes & fees
15 Sept - 16 Sept
Cozy Catskill Escape
Property grounds

8. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is HK$1,568
HK$2,678 total
includes taxes & fees
20 Sept - 21 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Property grounds

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,936
HK$4,063 total
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
TV

10. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is HK$1,129
HK$2,243 total
includes taxes & fees
23 Sept - 24 Sept
Cabin Oasis near Town
Exterior detail

11. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 HK$1,921
HK$3,969 total
includes taxes & fees
30 Sept - 1 Oct
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Coffee/tea maker, fridge, microwave, oven

12. NEW: Chic Family Home in Boutique Town

NEW: Chic Family Home in Boutique Town
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is HK$1,337
HK$5,304 total
includes taxes & fees
15 Sept - 16 Sept
NEW: Chic Family Home in Boutique Town
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 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 HK$2,487
HK$4,372 total
includes taxes & fees
15 Sept - 16 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, books

14. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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 HK$1,751
HK$5,535 total
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
Exterior

15. 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 HK$1,254
HK$2,676 total
includes taxes & fees
15 Sept - 16 Sept
Modern Luxurious Cabin, Catskills - The Tiny Nook
TV, fireplace, printers

16. 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)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is HK$4,438
HK$10,413 total
includes taxes & fees
9 Sept - 10 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

17. 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 HK$3,104
HK$5,944 total
includes taxes & fees
21 Sept - 22 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Property grounds

18. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is HK$1,984
HK$4,166 total
includes taxes & fees
30 Sept - 1 Oct
Larkspire I Sleepy Hollow Lake I Beach & Firepit
Interior

19. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is HK$2,627
HK$4,882 total
includes taxes & fees
14 Sept - 15 Sept
Luxury Barn Retreat — All-Season Escape Awaits!
Exterior detail

20. 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.
8 Acre Estate w Hot Tub, Deck, Fire Pit & 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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Top Craryville Hotel Reviews

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"We stay here all the time. Love everything about this place. Front staff is amazing. The dipping pools are amazing. Rudy, the bartender best guy ever at the bar, have to see him. You will not be disappointed. Great location also"
hans 2-night trip
Posted 4 hours ago
Pocketbook Hotel and Bath

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