Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

The Calf Pen
10.0 out of 10, Exceptional, (22)
"We had a great stay! "
The Calf Pen
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (30)
"We had a wonderful time in this cabin in the woods. We saw fireflies, a bear, a fox and countless deer. The Wifi was great so the adults could work while the kids were at camp. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (85)
"Each year we go on vacation with our daughter, son in law and his family. We are a group of 12 and loved this lake house. We all want to make this our yearly trip. Great place"
The price is NZ$1,132
includes taxes & fees
14 Oct - 15 Oct
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
The Catskills Red Barn
10.0 out of 10, Exceptional, (32)
"Everything was perfect and as described. Lots to check out! Host was excellent to communicate with."
The Catskills Red Barn
Leaf SZN at Birch Creek Retreat - 8br, 8ba, new hot tub + sauna
10.0 out of 10, Exceptional, (88)
"Our family stayed for five days surrounding my daughter’s wedding in the area. The kitchen is absolutely fabulous and each room has its own personality and convenient bathroom. The surroundings were gorgeous and relaxing on the porch helped us to wind down from all the wedding stress. The owner quickly responded to all our questions and we felt very spoiled! I highly recommend Birch Creek Retreat. 😀"
Leaf SZN at Birch Creek Retreat - 8br, 8ba, new hot tub + sauna
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is NZ$2,488
includes taxes & fees
28 Sept - 29 Sept
Hudson River Way by Woodstock Way Hotel
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (87)
"Very nice property. Very nice owner. No problems noted."
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (94)
"Hard to decide where to begin…one of the nicest rental homes in the Windham area! Outside amenities are incredible - the firepit is amazing, the outdoor kitchen provides so many wonderful options (outdoor pizza oven was a hit) The inside provides fabulous space for all - even when the weather doesn’t cooperate. Rick and Alan were a pleasure to deal with. We look forward to a return trip!"
Tuscan Year Round Beauty - Pickleball Court
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 NZ$1,249
includes taxes & fees
2 Oct - 3 Oct
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Esopus Creek modern Tiny house Retreat!
9.4 out of 10, Exceptional, (11)
"We were in town for a family gathering and this house was in a great location and was exactly as described."
The price is NZ$361
includes taxes & fees
29 Sept - 30 Sept
Esopus Creek modern Tiny house Retreat!
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (13)
"Very peaceful location in our favorite Hudson Valley town, sweet Saugerties! The property manager was extremely responsive, the neighbors were very nice — one even recommended a local swimming hole — and the house was very cute and unique. We loved waking up to the sound of birds and the sunrise over the Hudson. We also loved being able to walk into the village center for dinner and ice cream. The house was clean, comfortable, and we very much enjoyed our stay. "
Historic Saugerties Home w/ Deck: River Views!
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths close to everything
10.0 out of 10, Exceptional, (35)
"We loved our stay !! Place was super clean and Mario was terrific to communicate with. He gave us tips for hikes and fun adventures and answered any questions we had right away. We can’t wait to come back !! "
The price is NZ$1,223
includes taxes & fees
28 Sept - 29 Sept
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths close to everything
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
9.4 out of 10, Exceptional, (3)
"My wife and I enjoyed staying in this A-frame with our dog for a few days. It had some simple, yet, well-chosen furnishing and decorations. Importantly, it was clean and welcoming. We were concerned about the proximity to route 87, and indeed you can see cars through gaps in the trees and hear the traffic if you are outside. Inside, however, was very quiet and we couldn't even hear a heavy down pour of rain."
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
Cleo’s Cabin: Private Retreat with Fenced Dog Run
8.8 out of 10, Excellent, (8)
"We were in town for HITS and this was a great place to spend a few nights! The cabin had everything we needed and was exactly as pictured online. Beds were super comfortable too. Highly recommend! "
Cleo’s Cabin: Private Retreat with Fenced Dog Run
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
10.0 out of 10, Exceptional, (34)
"My partner and I so enjoyed our 3 night stay in such a spacious and clean place. They even Provided eggs milk butter champagne and welcome cookies. That was a first!! Walking distance to lots of fine restaurants and sights and a private garden backyard as well. We will definitely return again Alex and Brian. Ithaca "
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Private + Peaceful 2 BR w/ River Views
10.0 out of 10, Exceptional, (7)
"I took my husband on a mystery weekend to upstate NY and arranged to have our friends from Ithaca meet us in Clementon. We loved the house. Found it welcoming and easy to manage - beautiful and clean. We went to OPUS 40 and did some other exploring in the area and enjoyed relaxing in the house and reconnecting with our friends. "
Private + Peaceful 2 BR w/ River Views
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
10.0 out of 10, Exceptional, (2)
"This property is perfectly located between Saugerties and Kingston with easy access to both. We wanted a place that was easy to explore the area from and we scored with this house. Everything was clean and we were provided with everything we could need, pots & pans, soap & shampoo, washer & dryer--all of it. We also had plenty of room to do the work we brought with us. The house stayed cool the whole time (day & night) and we really enjoyed it. "
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (196)
"Very accommodating host! Thanks for the stay. Definitely consider staying again! Lovely layout, airy, roomy. Host generous with paper goods etc. Thanks for a great vacation!"
Beautiful House 0,5 Mile From Hunter Mountain
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (168)
"Our late summer visit to the Catskill Mountains was very relaxing even with a 2-year-old. The kids enjoyed the pool the most and the property owners provided many pool toys for all. We enjoyed the hot tub also. There was plenty of room. WIFI was spotty, but no one had to work and that forces us to relax. Everyone reported they had a great time. Family time is the most important gift. Thank you Pete and Lara "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
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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 Woodstock

Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (216)
"This was our second time staying at this beautiful home and we will be back again! "
The price is NZ$509
includes taxes & fees
15 Oct - 16 Oct
Streamside Cottage Half Mile to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (37)
"IT WAS IDYLLIC."
The price is NZ$447
includes taxes & fees
13 Oct - 14 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (30)
"We had a wonderful time in this cabin in the woods. We saw fireflies, a bear, a fox and countless deer. The Wifi was great so the adults could work while the kids were at camp. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
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.