Photo by Michelle Rapier

Search Vacation Homes in Castleton-on-Hudson

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Castleton-on-Hudson

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is SAR 604
SAR 1,815 total
includes taxes & fees
9 Sep - 10 Sep
Comfortable Berkshires retreat on mtn resort, SISO

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

9.0 out of 10, Wonderful, (28)
"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!

Charming 3-bedroom house with WiFi, AC in delightful Hudson

2.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, great communication with owner, excellent location! "
Charming 3-bedroom house with WiFi, AC in delightful Hudson

Home away from home

8.0 out of 10, Very Good, (18)
"Very cozy and comfy place!"
Home away from home

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (52)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Pet-Friendly Latham Retreat ~ 7 Mi to Albany!

8.6 out of 10, Excellent, (19)
"Great location, close to the school, and super convenient for grad weekend! The hosts were very responsive and helpful. Two small bedrooms with a nice upstairs bathroom- extra large. Great for family vs hotel. I would highly recommend to Siena families for any events/games/etc. "
Pet-Friendly Latham Retreat ~ 7 Mi to Albany!

Stylish Home on Union St

Stylish Home on Union St

Catskill Mountain House private 5 acre backyard, Golf, Ski, Hike, Boating, Fish

8.8 out of 10, Excellent, (27)
"Elizabeth is very hospitable and the property is very nice. Would definitely stay here again. "
Catskill Mountain House private 5 acre backyard, Golf, Ski, Hike, Boating, Fish

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.4 out of 10, Exceptional, (16)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is SAR 1,820
SAR 3,009 total
includes taxes & fees
16 Sep - 17 Sep
The Lakeshore House

Watervliet Retreat

9.8 out of 10, Exceptional, (8)
"My son graduated from Sienna College on Sunday. Our family was ver comfortable. Three private cozy bedrooms. Central air made it very comfortable. The place is very clean and beautifully decorated. With all the comforts of home. Markos was a fabulous host. Thank You newly renovated. "
Watervliet Retreat

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

10.0 out of 10, Exceptional, (95)
"Very cool and private!"
Located in the beautiful Heldebergs, This is a cute little house you will love.

All the comforts of home

9.0 out of 10, Wonderful, (24)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is SAR 399
SAR 530 total
includes taxes & fees
24 Aug - 25 Aug
All the comforts of home

Lakefront Luxe: Kayak & SUP From Private Dock, Pong & Air Hockey, Near Hudson

10.0 out of 10, Exceptional, (136)
"I booked this house for a girls weekend, there 6 of us and we had such a nice Time. I had excellent and clear communication with Nicole and Dave, the house was very clean and welcoming. I highly recommend this house for your next getaway in that area. "
Lakefront Luxe: Kayak & SUP From Private Dock, Pong & Air Hockey, Near Hudson

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (114)
"Our family of eight adults stayed in the home to celebrate a college graduation. It has a nice open floor plan that accommodated in-door time together as the weather was chilly for our stay. The nice balcony overlooks the lake. Only drawbacks are that there’s just one shower and futon sofa mattress was hard, not comfortable. Overall, very nice house and happy with our stay. "
3 Bedroom Lakefront Home with Hot Tub & Fireplace

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

10.0 out of 10, Exceptional, (9)
"Nice spacious house with everything you could need for a short or long stay. We especially loved hanging out in the beautiful sunroom overlooking private backyard. Host was communicative and accommodating. Would highly recommend and consider staying again!"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Huge Family Home; Centrally Located in the Capital Region!!!

10.0 out of 10, Exceptional, (1)
"Beautiful home in a very cool neighborhood. Lots of great amenities. We really enjoyed staying there. "
Huge Family Home; Centrally Located in the Capital Region!!!

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is SAR 923
SAR 1,925 total
includes taxes & fees
25 Aug - 26 Aug
Near Tanglewood: Historic Summer Retreat

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (6)
"A very good place to stay. Best of all, each bedroom has its own bathroom. There's plenty of hot water, even if multiple people are showering at the same time. The only downside to me is that the washer is broken when we checked in. We want to come again!"
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

Comfortable unique space

10.0 out of 10, Exceptional, (7)
"We had a great time. House has everything you need. Could benefit from some deep cleaning. Owner is very nice & communicated often with us. We had our dog and he was perfectly content. "
Comfortable unique space
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Castleton-on-Hudson Hotel Reviews