Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock and around

Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"My teen daughters and I had a wonderful stay. The property is absolutely charming, a true Hudson Valley gem. Neighboring towns, hiking trails, farms are a perfect getaway place and reprieve from NYC bustle. The cricket and frog chirps at dusk an absolute bonus :)"
The Farm at Hyde Park
Pool
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
8.8 out of 10, Excellent, (5)
"Stay, house, check in were all great. It was pretty far to Hunter mountain but the house was perfect for our little getaway!"
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Exterior
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is €245
per night
9 May - 10 May
The Studio at the Inn at High Falls
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Property grounds
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (105)
"Great location. Comfortable space. The only drawback was the downstairs bedroom mattress."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Property grounds
Renee's Get-Away New Paltz
9.8 out of 10, Exceptional, (13)
"perfect for what we needed. We only needed a place to sleep since we were visiting our daughter and had several plans throughout the trip. The be was comfortable and it was the perfect size place for my wife and I, as well as my 20yo daughter who stayed 2 nights."
Renee's Get-Away New Paltz
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (67)
"We travel to the Catskills at least once a year and stay at various locations. What sets this property apart is the true seclusion and absolutely no distractions from the nature around you. Even though it is close to hubs like Wyndham and Hunter (less than 20 to both) when sitting outside it feels like you are in the middle of nowhere. Inside is clean, cosey by the fire, and lots of fun things to do with our teenagers. Definitely would stay again."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (103)
"Great comfortable home with all the amenities we could have asked for! Loved the games there to entertain us and the vestigial fireplace to relax at at night. Close by to area hiking and short drive into town!"
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Fridge, microwave, stovetop, dishwasher
Saugerties Home: 3 Decks & Hudson River View
9.8 out of 10, Exceptional, (9)
"This is a great place to stay. Clean and comfy and in a beautiful area. We didn't find the promised linens for the sofa bed, but maybe we just weren't looking in the right place. Other than that, we were very pleased... do pay attention to the notes about the stairs... there are a fair few of them."
Saugerties Home: 3 Decks & Hudson River View
Smart TV, offices
Indulge in an Elegant Upstate Getaway
10.0 out of 10, Exceptional, (39)
"We've stayed at this house 4 times--for several days each time--and it was, as always, incredibly comfortable and lovely. The house is beautiful and always spotless, and the kitchen is a pleasure to use. I would highly recommend. We rent houses in the Rhinebeck area several times throughout the year and this house is always our first choice."
Indulge in an Elegant Upstate Getaway
Exterior
Last minute deal!! Scandinavian BBQ hut and Hot tub
10.0 out of 10, Exceptional, (54)
"We enjoyed our stay. Having so many outdoor things was great (fire pit, the bbq house, she shed, hot tub). It was a close drive to Hunter and Windham for skiing and dining out. The kitchen was also well stocked with pots, pans etc."
Last minute deal!! Scandinavian BBQ hut and Hot tub
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Fridge, microwave, oven, stovetop
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is €245
per night
5 Jun - 6 Jun
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Dining
The Solarium: Woodstock Retreat w/Hot tub+Stream!
10.0 out of 10, Exceptional, (1)
"This place was a gem to sit back, relax and take in the scenery. The owner was very accommodating. I highly recommend staying."
The Solarium: Woodstock Retreat w/Hot tub+Stream!
1 bedroom, free WiFi, bed sheets
The Loft At The Inn At High Falls
8.0 out of 10, Very good, (6)
"Wish we could have stayed longer. It was a perfect overnight after the meadowlark music festival in stone ridge"
The price is €332
per night
9 May - 10 May
The Loft At The Inn At High Falls
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (250)
"Very clean, and the little things really made a difference: nice sheets, shampoo and soap provided, quality towels. We would stay here again for sure."
The price is €792
per night
9 May - 10 May
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Exterior
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
10.0 out of 10, Exceptional, (136)
"Wonderful Ambience and very accommodating for children and pets. The game room was a bonus and a 'winner' - for us."
ONE CLOVEWOOD in HIGH FALLS, near Mohonk preserve, mountain bikes included
Fridge, microwave, oven, stovetop
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
10.0 out of 10, Exceptional, (5)
"We had a wonderful time. Excellent layout for a large group. I am sure it's beautiful right about now with the budding trees. We had a wonderful stay!"
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Fridge, microwave, oven, stovetop
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (83)
"The property was very comfortable with plenty of room for the 8 of us to hang out, cook, and enjoy meals together. Would definitely return!"
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
Fridge, microwave, oven, stovetop
Beautiful Hudson Valley Woodland Retreat with Swimming Pool. Pets welcome.
10.0 out of 10, Exceptional, (20)
"Excellent host and home, with everything exactly as pictured and described, looking forward to booking another stay here again."
Beautiful Hudson Valley Woodland Retreat with Swimming Pool. Pets welcome.
Don't see what you're looking for?
See all available properties in Woodstock
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.

Other property types in Woodstock

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is €305
per night
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
1 bedroom, internet, bed sheets
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is €209
per night
14 May - 15 May
Hotel Woodstock - Iris suite
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is €139
per night
15 May - 16 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.

Woodstock Holiday Homes information

Number of reviews
820
Accommodation
725 Holiday Homes
Lowest Price
€245
Highest Price
€783

Recent Reviews in Woodstock
Expedia verified reviews