A misty forest landscape with a hill in the background.

Search Vacation Homes in Craryville

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Craryville vacation 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, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,769
￥22,319 total
includes taxes & fees
Oct 12 - Oct 13
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, (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 ￥50,580
￥101,863 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
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 ￥52,423
￥112,166 total
includes taxes & fees
Oct 11 - Oct 12
Perfect House In Hillsdale, Brings Friends & Fam
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)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥35,101
￥54,905 total
includes taxes & fees
Oct 13 - Oct 14
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.

5. 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 ￥35,054
￥74,940 total
includes taxes & fees
Oct 14 - Oct 15
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.

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 ￥31,580
￥54,292 total
includes taxes & fees
Oct 13 - Oct 14
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.

7. 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 ￥29,417
￥69,546 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
A staircase with a wooden handrail and a white wall with a light switch.

8. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 ￥30,791
￥48,504 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
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)
"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 ￥31,580
￥55,382 total
includes taxes & fees
Oct 13 - Oct 14
Sweet Cozy Victorian in Housatonic. Close to everything.
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.

10. 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 ￥89,814
￥210,028 total
includes taxes & fees
Oct 22 - Oct 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 ￥31,106
￥53,711 total
includes taxes & fees
Nov 8 - Nov 9
Cabin Oasis near Town
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

12. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ￥21,948
￥42,064 total
includes taxes & fees
Nov 8 - Nov 9
Modern cabin retreat
A kitchen with a central island, bar stools, and pendant lighting.

13. 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 ￥20,211
￥42,746 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Catskill Escape
A couple in a hot tub with a natural landscape in the background.

14. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (10 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 ￥41,054
￥92,315 total
includes taxes & fees
Oct 26 - Oct 27
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
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, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥63,160
￥109,704 total
includes taxes & fees
Oct 19 - Oct 20
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden deck with a wicker sofa, a hammock, and a grill.

16. Larkspire l Catskills Fall Foliage Lake House

Larkspire l Catskills Fall Foliage Lake House
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 ￥43,351
￥88,087 total
includes taxes & fees
Oct 12 - Oct 13
Larkspire l Catskills Fall Foliage Lake House
A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

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

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Great house for a last minute getaway. Super clean house!!! Such a cute house with a lovely porch and view. We loved looking at the vintage books on the bookshelf! House had everything we needed, towels, and even shampoo. Would stay again. Location was great too. Centrally located near many attractions but rural enough to relax!"
United States
kristen d.
The price is ￥21,317
￥54,823 total
includes taxes & fees
Oct 26 - Oct 27
Country House offers 2 bedrooms and a den, lots of parking.
Cook, gather, and connect with a central island

18. 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 ￥34,391
￥125,056 total
includes taxes & fees
Nov 3 - Nov 4
Catskill * Screened Porch * Chef’s Kitchen
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

19. 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 ￥39,080
￥121,035 total
includes taxes & fees
Oct 29 - Oct 30
Chic Barn Style * Fireplace * Near Stissing House
A spacious room with a wooden ceiling, large windows, and a chandelier.

20. 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 ￥67,282
￥116,846 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Barn Retreat — All-Season Escape Awaits!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Craryville Hotel Reviews

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Beautiful building. Glad to see it repurposed."
Vivien 1-night trip
Posted 12 hours ago
Pocketbook Hotel and Bath

Find out more about Craryville

Craryville Vacation Homes information

Number of reviews
354
Accommodation
645 Vacation Homes
Lowest Price
￥22,319
Highest Price
￥210,028