Photo by Bill Boyd

Holiday Homes in Kingston

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Featured Holiday Homes in Kingston

Cozy cabin with great views and fire place!

9.8 out of 10, Exceptional, (80)
"Great space and feel of upstate NY. Will return for sure "
Cozy cabin with great views and fire place!

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (50)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (69)
"This home was perfect for our Labor Day weekend reunion, with everything we would need, easy use of fire pit, grill, deck and kitchen (but there is no dishwasher). Gisele was great to communicate with. Would definitely go again!"
Beautiful, private Property/swimming pond

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (171)
"Everything was just perfect. The house was spacious and had so many wonderful amenities. Location was great, private and quiet. We enjoyed the hot tub under the stars each night to relax from the hiking! Highly recommend. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

Hunter Mountain Home w/ Game Room: 1 Mi to Skiing!

10.0 out of 10, Exceptional, (2)
"Stayed here with a few friends who were looking to get out of the city for the weekend. Nice place! Everything came as advertised, and it was nice to have a game room when it was raining."
Hunter Mountain Home w/ Game Room: 1 Mi to Skiing!

Hudson River Waterfront, Leaf Peepers Welcome, 3 Bdrm w Pool/Quiet Street

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Hudson River Waterfront, Leaf Peepers Welcome, 3 Bdrm w Pool/Quiet Street

Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia

2.0 star property
The price is AU$539
includes taxes & fees
2 Dec - 3 Dec
Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is AU$1,397
includes taxes & fees
2 Dec - 3 Dec
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

Beautiful House 1 Mile From Hunter Mountain

9.6 out of 10, Exceptional, (121)
"My family really enjoyed their stay at this house. The kids were super excited about the game room. The house is very clean and in a perfect location for the activities you want to do. They have everything you need to make your vacation as enjoyable as possible. Communication with the host was excellent, he was an accessible person. Highly recommended."
Beautiful House 1 Mile From Hunter Mountain

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (169)
" Beautiful house! Great location! The house overall exceeded our expectations! A bit bright in the mornings, good to know in case you are looking to try and sleep in. King bed in the master is super comfortable and the shower is awesome! Would definitely stay again."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

9.8 out of 10, Exceptional, (7)
"Our stay was really nice. The house was clean and had everything we needed. We loved being able to walk into town. "
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

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

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (90)
"The house and its amenities were perfect for our group, and the host was easy to communicate. "
The price is AU$1,029
includes taxes & fees
2 Dec - 3 Dec
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

CREEK MOUNTAIN VIEWS IN CATSKILL RETREAT.. with weekly discounts.

9.8 out of 10, Exceptional, (36)
"The property was absolutely beautiful and the location was great not too far from the town and yet the property felt secluded and private. Great communication with the host and there was a very helpful instruction and information book as well as instructions for just about everything in the house. I am looking forward to my next stay at the property "
CREEK MOUNTAIN VIEWS IN CATSKILL RETREAT.. with weekly discounts.

5-Star New Barn Home - Music Studio, Views & Hot Tub

10.0 out of 10, Exceptional, (25)
"House was just as described, easy check in, immaculately clean throughout, well stocked with wood for the fireplaces and very responsive host. Would come back without hesitation. "
5-Star New Barn Home - Music Studio, Views & Hot Tub

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!

SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 3 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (87)
"The house and property were great. Very comfortable house that felt like home with a well equipped kitchen, two living rooms, great beds, fireplace, and spa. Pool was closed since it was winter. The property is wooded and feels like being in your own private park but is only a few minutes from downtown. Highly recommended!"
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 3 MINUTES FROM TOWN

Winter Ski House with gym +spa access

9.4 out of 10, Exceptional, (16)
"We were happy to see there was a full sized kitchen beautifully renovated with a back door to the nice back yard in addition to the wonderful bedroom accommodations. Lots of nice amenities plus antique furnishings but updated baths, just lovely. My only suggestions is more pillows."
The price is AU$354
includes taxes & fees
2 Dec - 3 Dec
Winter Ski House with gym +spa access
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 Kingston

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (20)
"Fantastic stay in the campfire cottage! Every detail was taken care of, from extra toothpaste (I always forget mine!) to the Nespresso machine. Cottage was very clean and cozy, communication was excellent. Would definitely return!"
The price is AU$278
includes taxes & fees
15 Dec - 16 Dec
Campfire Cottage: Fireplace, fire pit & no chores!

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

9.6 out of 10, Exceptional, (17)
"This apartment was clean and comfortable, and matched the online description. It was not particularly quiet: there is a bar next door, additional VRBO guests upstairs, and trains passing through the neighborhood throughout the night. But the owners provide white noise machines and earplugs, and the noise didn't disrupt my sleep at all. "
The price is AU$373
includes taxes & fees
2 Dec - 3 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.