Photo by Michelle Rapier

Castleton-on-Hudson Holiday Rentals

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Castleton-on-Hudson

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1938)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$199
includes taxes & fees
27 Aug - 28 Aug
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, (959)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is AU$272
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (113)
"Beautiful grounds with the most gracious of hosts. Lovely accommodations! Will stop there again!"
The price is AU$223
includes taxes & fees
10 Aug - 11 Aug
Micosta Leisure Inn
Huttopia Berkshires
Deluxe Tent

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (1)
"Huttopia Berkshires was wonderful! Very peaceful and a beautiful view. We enjoyed the on-site coffee shop/cafe and our tent with a deck and indoor plumbing! The staff was extremely friendly and helpful. The pool is lovely. Highly recommend!"
The price is AU$168
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
cozy retreat with modern amenties
In-room dining

cozy retreat with modern amenties

2.0 star property
cozy retreat with modern amenties
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AU$275
includes taxes & fees
9 Aug - 10 Aug
Taborton Harvest Boulder Pines Cabin in the woods
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is AU$275
includes taxes & fees
9 Aug - 10 Aug
Taborton Harvest Timber Trails Unique cabin experience
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (84)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
The Rizzy Apartment
Smart TV

The Rizzy Apartment

7.2 out of 10, Good, (5)
"Great time "
The price is AU$347
includes taxes & fees
19 Aug - 20 Aug
The Rizzy Apartment
3 bedroom with free parking
Interior

3 bedroom with free parking

6.0 out of 10, (1)
"1. Floors wet when we arrived because they had just been mopped. There was water oozing from the flooring in the kitchen. When dry the floors were sticky.2. The bathroom sink barely drained. We finally just used the kitchen sink. The shower drained better but stillstanding in water while showering.3. There were two bath towels and two washcloths left on the dining room table upon our arrival. In the kitchen there was a roll of paper towels. No hand towels or kitchen towels provided.4. All...
The price is AU$175
includes taxes & fees
24 Aug - 25 Aug
3 bedroom with free parking
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,721
includes taxes & fees
18 Aug - 19 Aug
Hancock Village Inn at Jiminy Peak
2 bedroom town house with game room
Fridge, microwave, oven, stovetop

2 bedroom town house with game room

5.8 out of 10, (16)
"Property was easy to get to. Located right off the thruway. House was clean and located close to plenty of shopping options. There was also fast food restaurants located within walking distance. "
2 bedroom town house with game room
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Terrace/patio

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (165)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Outdoor banquet area

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (88)
"Our group had a great time. The place is a bit dated but has room for plenty of people."
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$759
includes taxes & fees
11 Aug - 12 Aug
Comfortable Berkshires retreat on mtn resort, SISO
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Interior

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 couples home with free wifi
Interior

The couples home with free wifi

10.0 out of 10, Exceptional, (1)
"Very calm environment, owner/host very helpufl & easy to communicate with"
The price is AU$179
includes taxes & fees
10 Aug - 11 Aug
The couples home with free wifi
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, (48)
"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
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
The price is AU$579
includes taxes & fees
29 Aug - 30 Aug
Charming 3-bedroom Cabin for nature lovers
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
Sign in
Sign up, it's free

Top Castleton-on-Hudson Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a quick 1 night stay, but we would have stayed longer if we had the time! The basic suite was very large. The bed was comfortable, kitchen was well stocked with cutlery, wine glasses, etc. The front desk staff was perfectly polite and welcoming. I will say that it wasn't obvious when I booked that one has to do one's own dishes, take out the trash. Luckily I read reviews in advance (after booking) so it came as no surpise. Also I learned from other reviews that any restaurant is a healthy drive away, and no food is served on-site. So we knew going in to bring some snacks, and plan in time to drive to any restaurant. (This is just a minor convenience and I'm glad I read reviews before arriving so we weren't surprised.) We'd stay here again!"
Miriam 1-night trip
Posted 23 hours ago
Vacation Village in the Berkshires

Frequently asked questions

Are there holiday rentals in Castleton-on-Hudson?

Yes, there are holiday rentals close to the most popular sights in Castleton-on-Hudson, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Castleton-on-Hudson has a good selection of restaurants. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Castleton-on-Hudson has to offer?

Comfortable Berkshires retreat on mtn resort, SISO: This holiday home rental outside of Castleton-on-Hudson offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Castleton-on-Hudson?

Explore the area and family-friendly sights such as Destroyer Escort Historical Museum, or get out into nature at a spot like Hudson River. Brookview Station Winery and Schodack Island State Park are other places to visit while you're in town.

What’s a holiday rental in Castleton-on-Hudson like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castleton-on-Hudson. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.