Photo by Michelle Rapier

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Compare 254 Vacation Homes in Castleton-on-Hudson with updated reviews, rates, and availability.

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

Glamorous lake house on a mountain lake in upstate New York (max of 8 guests)

10.0 out of 10, Exceptional, (59)
"This house was beautifully appointed! Spotless and comfortable, the hostess is lovely and should write a handbook on “How to be a VRBO Hostess”"
Glamorous lake house on a mountain lake in upstate New York (max of 8 guests)

Vacation home just 11 minutes from MVP Arena

2.0 star property
9.6 out of 10, Exceptional, (12)
"Nii's place was very clean and served its purpose for our visit to Delmar. The property was exactly as the pictures showed it."
Vacation home just 11 minutes from MVP Arena

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

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

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

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 1,183
AED 2,442 total
includes taxes & fees
3 Feb - 4 Feb
Comfortable Berkshires retreat on mtn resort, SISO

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (105)
"The house was lovely; every bedroom was nicely furnished with plenty of linens. The kitchen was amazing and was a great place for everyone to gather around and cook; the way the table opened up to the outdoor space was wonderful, but since it was snowing, we didn't get to really use it. The bathrooms were stunning with really nice showers, and there were plenty of nice touches. Galina was kind host who was easy to reach. I would definitely stay again and recommend the place to anyone in the...
4 Bdrm Modern Victorian with Tree House and playground

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (64)
"We had a wonderful stay, thank you! "
The price is AED 1,153
AED 2,205 total
includes taxes & fees
5 Feb - 6 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is AED 2,196
AED 3,853 total
includes taxes & fees
4 Feb - 5 Feb
Hancock Village Inn at Jiminy Peak

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

9.0 out of 10, Wonderful, (21)
" The house has a beautiful location and the view of the lake is beautiful. There are several things to do in the surrounding areas such as hiking, horseback riding, shopping and nice restaurants. The house was overall nice. It has a combination of very nice updates and a few needed updates. The couches are extremely uncomfortable. Our host was responsive for the most part."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"House was very clean and nicely furnished. Big kitchen was helpful as a lot of cooking went on.Amanda was very helpful with suggestions about restaurants and places to visit. She quicky responded to text messages ."
The price is AED 551
AED 1,326 total
includes taxes & fees
3 Feb - 4 Feb
Near Tanglewood: Historic Summer Retreat

2 bedroom town house with game room

6.4 out of 10, (13)
"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."
The price is AED 422
AED 643 total
includes taxes & fees
3 Feb - 4 Feb
2 bedroom town house with game room

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

9.2 out of 10, Wonderful, (95)
"Great place to stay. Would stay here again. Had everything we needed."
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!

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

10.0 out of 10, Exceptional, (82)
"Erika’s cabin is exceedingly cozy and perfect for a weekend getaway from the city. Communication was a breeze. The cabin was super comfy to hang out in and located very close to a beautiful state park. Would definitely recommend staying here!"
Located in the beautiful Heldebergs, This is a cute little house you will love.

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Our stay at the Spencer House was absolutely perfect! The house was spotless, with every detail thoughtfully attended to. There was an abundance of towels and toiletries, making our stay feel effortlessly luxurious. Each bedroom was incredibly spacious and had its own en suite bathroom, providing comfort and privacy for everyone in our group.The host was amazing—so accommodating and responsive. She went out of her way to make sure we had everything we needed, from a great selection of board...
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

Cozy, Private1-bedroom in charming Schenectady with Private Bathroom

9.0 out of 10, Wonderful, (4)
"The room is as described and shown in the photo and as mentioned in earlier comments the fence has a gap so it’s still a leash required yard, but they have designed a privacy passage between the room and the bathroom so concerns about that have been eliminated. We had trouble with the key box but help arrived quickly when we got there, and they provided everything needed for a lovely stay with my two pups. "
The price is AED 294
AED 419 total
includes taxes & fees
1 Mar - 2 Mar
Cozy, Private1-bedroom in charming Schenectady with Private Bathroom

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (110)
"Completely comfortable. A"
3 Bedroom Lakefront Home with Hot Tub & Fireplace

Cozy log cabin in Lake Community.

10.0 out of 10, Exceptional, (19)
"My wife, son, and I couldn’t have been more comfortable in this beautiful cabin and community. We loved hanging out on the back porch and playing games in the basement. Nice location - short drives to ski in Windham and dine in Hudson. Thanks again for a memorable stay, and we hope to be back soon. "
Cozy log cabin in Lake Community.

3BR w/ Hot Tub - 22 min to Windham & Hunter Skiing

The price is AED 710
AED 1,643 total
includes taxes & fees
3 Feb - 4 Feb
3BR w/ Hot Tub - 22 min to Windham & Hunter Skiing
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

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is AED 551
AED 641 total
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (924)
"Staff was exceptionally helpful and friendly."
The price is AED 694
AED 761 total
includes taxes & fees
3 Feb - 4 Feb
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (92)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is AED 477
AED 515 total
includes taxes & fees
17 Feb - 18 Feb
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.