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Compare 795 Vacation Homes in Woodstock with updated reviews, rates, and availability.

The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Front of the Red Cottage
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (33)
"Loved the house. Pictures don’t do it justice. We had a few issues and the property manager was super responsive and had everything corrected. Would stay there again. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
JUNE 2024 --Plenty of parking + electric charging
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.
The Catskills Red Barn
The Catskills Red Barn
The Catskills Red Barn
10.0 out of 10, Exceptional, (36)
"Really cute weekend stay for my partner, pup and I. Easy access to the main road which was very convenient and great yard for the dog! Bathroom needs a little updating :) "
The Catskills Red Barn
Bright, historic Woodstock home close to town
Exterior
Bright, historic Woodstock home close to town
9.6 out of 10, Exceptional, (5)
"We loved the historic nature of the property. It is in a beautiful setting, just a short walk from downtown Woodstock. Cheryl was very responsive and helpful. Wish we had more time to enjoy the outdoor space!"
Bright, historic Woodstock home close to town
Studio 3 BEDS-SLEEPS 3
Parking
Studio 3 BEDS-SLEEPS 3
9.4 out of 10, Exceptional, (26)
"Very accommodating. Easiely accessible. Loved the balcony!"
The price is AED 294
AED 477 total
includes taxes & fees
10 Nov - 11 Nov
Studio 3 BEDS-SLEEPS 3
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
Balcony
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
9.0 out of 10, Wonderful, (38)
"I would totally recommend! It was a very practical apartment. I stayed with my spouse and my parents. The location was great, the manager was very arranging with the check-in time, and we really appreciated that we had two floors and two full bathrooms, one for my parents, and one for me and my spouse. Wish we had stayed longer to take advantage of the nice balcony"
The price is AED 441
AED 716 total
includes taxes & fees
7 Nov - 8 Nov
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
Exterior
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
10.0 out of 10, Exceptional, (6)
"My family stayed here while visiting our daughter for parents weekend at Bard College. We have stayed in a number of rentals in the area over the past few years, and this is by far the best! It was perfect in every way: spacious, very clean and comfortable, everything worked well and the hosts were super responsive and kind. We will absolutely want to stay here again! "
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
Hamptons on the Hudson in South Saugerties
Pool
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (12)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Exterior
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 AED 1,414
AED 2,854 total
includes taxes & fees
26 Nov - 27 Nov
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
Property grounds
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (89)
"It is a gorgeous house on the lake. The guests enjoyed every moment of our stay there!!"
The price is AED 1,396
AED 2,520 total
includes taxes & fees
7 Nov - 8 Nov
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
A'Neils Windham Ski Lodge & Family Retreat
Front Porch
A'Neils Windham Ski Lodge & Family Retreat
10.0 out of 10, Exceptional, (25)
"Beautiful historic house in Windham NY, great for large gatherings. Plenty of bedrooms with multiple beds and private baths. Spacious common area to relax at the end of the day. Large dining room that will accommodate all your guests and a large well stocked kitchen with everything you need to cook and serve. Relax on the covered front porch and enjoy nature or challenge your guests in a game of pool. The house was very clean on arrival with easy check in access. All in all it’s a great place...
A'Neils Windham Ski Lodge & Family Retreat
Catskill Mountain Retreat -- private, beautiful views
imagine your morning coffee with that view
Catskill Mountain Retreat -- private, beautiful views
9.8 out of 10, Exceptional, (97)
"Our group is looking for a location with beautiful fall foliage and solitude. A place where we could reconnect and also find alone time mission accomplished. Looking forward to next year."
Catskill Mountain Retreat -- private, beautiful views
Esopus Creek modern Tiny house Retreat!
Interior
Esopus Creek modern Tiny house Retreat!
9.6 out of 10, Exceptional, (17)
"A great spot close to Woodstock ny"
The price is AED 569
AED 830 total
includes taxes & fees
11 Nov - 12 Nov
Esopus Creek modern Tiny house Retreat!
Hudson River Way by Woodstock Way Hotel
Exterior
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is AED 1,262
AED 1,404 total
includes taxes & fees
19 Nov - 20 Nov
Hudson River Way by Woodstock Way Hotel
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Exterior
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
10.0 out of 10, Exceptional, (176)
"It was a perfect stay it’s such a perfect lovely place. Highly recommend "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
463ee7f1-9352-4a85-aa7b-caebfdcb9d5e
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
10.0 out of 10, Exceptional, (9)
"What a special place. The overlook is gorgeous and the entire home was so relaxing. Perfect stay. "
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
The open dining and living room area has plenty of comfortable seating.
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
10.0 out of 10, Exceptional, (1)
"Host was great! This house has everything you need for a perfect upstate stay. Quiet neighborhood close to all amenities and local attractions. "
The price is AED 569
AED 938 total
includes taxes & fees
7 Nov - 8 Nov
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Charming 3-bedroom house in marvelous Hunter. Hot Tub, Pool Table, Ski, Lakes
Property grounds
Charming 3-bedroom house in marvelous Hunter. Hot Tub, Pool Table, Ski, Lakes
10.0 out of 10, Exceptional, (3)
"My friends and I had an amazing stay at Isabel's home. The rooms were comfy, the amenities were perfect for our trip, and the kitchen comes very well equipped for all of your trip needs. I would gladly rebook this home for future trips to upstate NY."
The price is AED 1,192
AED 2,202 total
includes taxes & fees
7 Nov - 8 Nov
Charming 3-bedroom house in marvelous Hunter. Hot Tub, Pool Table, Ski, Lakes
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
Front Entrance to Cottage
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (222)
"The property was beautiful and secluded providing the peaceful getaway from the city that we needed. The host is also incredibly friendly and provided the easiest check in/out process I’ve seen. Loved Woodstock! "
Streamside Cottage Half Mile to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Teahouse
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (38)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is AED 661
AED 1,028 total
includes taxes & fees
10 Nov - 11 Nov
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Front of the Red Cottage
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (33)
"Loved the house. Pictures don’t do it justice. We had a few issues and the property manager was super responsive and had everything corrected. Would stay there again. "
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.