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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 319 Vacation Homes in Castleton-on-Hudson with updated reviews, rates, and availability.

Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
Romantic Villa
Fridge, microwave, oven, stovetop

Romantic Villa

10.0 out of 10, Exceptional, (21)
"The property was lovely, quiet, and clean. The host will truly go out of her way to be very sure that your stay meets your needs. "
Romantic Villa
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (22)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Secluded Lux Mansion Pool Home with Amazing Views
Fridge, microwave, oven, stovetop

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Outdoor pool, a heated pool

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests
Property grounds

PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests

9.2 out of 10, Wonderful, (98)
"Great place to stay. Would stay here again. Had everything we needed."
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Fridge, microwave, oven, stovetop

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Located in the beautiful Heldebergs, This is a cute little house you will love.
Miscellaneous

Located in the beautiful Heldebergs, This is a cute little house you will love.

10.0 out of 10, Exceptional, (85)
"This was the perfect place for my family to stay"
Located in the beautiful Heldebergs, This is a cute little house you will love.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
4 Bdrm Modern Victorian with Tree House and playground
Terrace/patio

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (110)
"Large kitchen and living space, great outdoor deck."
4 Bdrm Modern Victorian with Tree House and playground
Game Room + Deck: Secluded Catskills Retreat
Fridge, microwave, stovetop, dishwasher

Game Room + Deck: Secluded Catskills Retreat

10.0 out of 10, Exceptional, (4)
"Another great stay at this beautiful home!"
Game Room + Deck: Secluded Catskills Retreat
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Lake house with a game room
Pool

Lake house with a game room

10.0 out of 10, Exceptional, (21)
"We had a wonderful stay! The spotless home is incredibly well equipped. The game room added hours of fun with pool and shuffle board tournaments. The hosts are very responsive. "
Lake house with a game room
Spacious 5-bed house centralized within hour of skiing, Race track & Lake George
Interior

Spacious 5-bed house centralized within hour of skiing, Race track & Lake George

10.0 out of 10, Exceptional, (1)
"Spacious home for my family to gather during a death in our family. Great communication with host, house was very well equipped with everything you could need. Thank you."
Spacious 5-bed house centralized within hour of skiing, Race track & Lake George
Pet-Friendly Latham Retreat ~ 7 Mi to Albany!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Latham Retreat ~ 7 Mi to Albany!

8.0 out of 10, Very Good, (18)
"Thanks, we had a good time!!"
Pet-Friendly Latham Retreat ~ 7 Mi to Albany!
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Outdoor pool, a heated pool

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

9.6 out of 10, Exceptional, (25)
"Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime."
The price is AED 2,204
AED 3,976 total
includes taxes & fees
13 May - 14 May
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Property grounds

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (34)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Fridge, microwave, oven, stovetop

Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

10.0 out of 10, Exceptional, (48)
"We were very happy with our stay. The house was as described and pictured in the listing. Well stocked for our needs, spare toothbrush, coffee, etc. Would definitely stay again!"
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community
Exterior

Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

10.0 out of 10, Exceptional, (2)
"Comfortable, clean , easy. "
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is AED 591
AED 1,735 total
includes taxes & fees
2 May - 3 May
Comfortable Berkshires retreat on mtn resort, SISO
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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Other property types in Castleton-on-Hudson

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is AED 434
AED 525 total
includes taxes & fees
12 May - 13 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
4 May - 5 May
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is AED 477
AED 515 total
includes taxes & fees
18 May - 19 May
Micosta Leisure Inn
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.