Woodstock Vacation Rentals

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Browse Select Woodstock Vacation Homes

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, (85)
"As we drove up the long driveway to this house we quickly felt it was a home for the next few days we stayed there. The space was inviting, comfortable, clean and the decor was beautiful. Our daughter absolutely loved celebrating her 13th birthday at this beautiful home. It was instant relaxation as the surroundings are beautiful and quiet. Gretchen was a lovely host who was very easy to communicate with and provided such helpful information for us during our stay. A few weeks later and we are...
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Save an average of 15% on thousands of hotels when you're signed in
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
Fridge, microwave, oven, stovetop
Catskills Getaway: 3BR, Pool, Hot Tub, Firepit, Ping-Pong, minutes from Hudson
10.0 out of 10, Exceptional, (1)
"This place is such a great value—beautiful, private, well thought out. Upon entering the cozy home, we were greeted with warmth and comfort. House has everything you need to make you feel at home. One of the highlights of our stay was the well-equipped kitchen. We prepared delicious meals and enjoyed our creations in the charming dining area. I recommend this house to anyone seeking a cozy getaway with friends and family."
Catskills Getaway: 3BR, Pool, Hot Tub, Firepit, Ping-Pong, minutes from Hudson
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
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
Property grounds
Catskill Vacation Rental: Private Deck & Fire Pit
10.0 out of 10, Exceptional, (2)
"This is a great place. The interior furnishings are welcoming and a cool retro style. The household goods are top notch. Super convenient for groceries, drug stores, restaurants. An easy hop to Albany. The fire pit is a nice place to relax. We'll return!"
Catskill Vacation Rental: Private Deck & Fire Pit
Fridge, microwave, oven, stovetop
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
10.0 out of 10, Exceptional, (82)
"Great country house, well situated near town, with stream in the rear. Would definitely stay here agin. Excellent communication with the owner, whose attention to detail helps to make this a comfortable stay. Well equipped kitchen -- pretty much everything you might need. This is a cozy house, not a fancy house. Very comfortable for a family. Stairs are a bit steep for little kids with kids beds upstairs."
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
Exterior
Last minute deal!! Scandinavian BBQ hut and Hot tub
10.0 out of 10, Exceptional, (55)
"My family and I stayed here for an early spring getaway with our dog. The property is very cute and perfect for a family. The pizza oven was a fun addition and made for a nice evening with delicious food. The hot tub is also very nice. The house is not far from access to several walks and hikes."
Last minute deal!! Scandinavian BBQ hut and Hot tub
Fridge, microwave, oven, stovetop
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
10.0 out of 10, Exceptional, (13)
"The host was fantastic with details and communication. Can’t wait to stay here again."
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
Exterior
Lovely 2 bedroom apt around the corner from Rough Draft and Uptown Kingston
10.0 out of 10, Exceptional, (27)
"This property was perfect for our weekend in Kingston. Lovely neighborhood, lots of restaurants just blocks away, including Rough Draft bookstore/cafe/bar a block away which was a hit with the whole family. We hiked Mohonk Preserve by day and enjoyed the backyard and fire at night. Andrea left amenities that went above and beyond the usual rental. Highly recommend!"
Lovely 2 bedroom apt around the corner from Rough Draft and Uptown Kingston
Property grounds
The 212 Escape - Main House
10.0 out of 10, Exceptional, (1)
"This stunning, sun-drenched property had ample space for all of our guests and unique amenities (yoga room, sauna, etc.) that made it stand out from other rentals. Each of the bedrooms are well-sized and beautifully decorated."
The 212 Escape - Main House
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
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
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!!
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
Property grounds
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
9.8 out of 10, Exceptional, (80)
"Natalya was a great host! Property was very nice and great location to Hunter!"
The price is CA $680
CA $1,088 total
includes taxes & fees
May 19 - May 20
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Beach nearby, sun loungers
Special Second Day November discounts @ the River. Text host for discount
9.8 out of 10, Exceptional, (12)
"Beautiful views of the river and was close to all. Place was a bit dusty and the larger bedroom had a very hard bed. Owner was kind and communicative."
Special Second Day November discounts @ the River. Text host for discount
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, (196)
"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 CA $216
CA $438 total
includes taxes & fees
May 20 - May 21
Streamside Cottage Walking Distance to Town of Woodstock
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $245
CA $379 total
includes taxes & fees
Jun 2 - Jun 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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 Vacation Homes information

Number of reviews
799
Accommodation
740 Vacation Homes
Lowest Price
CA $170
Highest Price
CA $680

Recent Reviews in Woodstock
Expedia verified reviews