Woodstock Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (40)
"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 CA $258
CA $396 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (226)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
Streamside Cottage Half Mile to Town of Woodstock
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior

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
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (170)
"The house is lovely. Cozy and roomy at once. The main living room comfortably fit three couples w room to spare. We cooked, ate, played games (lots were offered), walked into town (many times). It was a beautiful setting and a perfect getaway weekend for our group. Highly recommend!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is CA $179
CA $205 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Starlite Motel
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (64)
"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
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is CA $179
CA $208 total
includes taxes & fees
Dec 29 - Dec 30
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
A-Frame of Mind
Exterior

A-Frame of Mind

10.0 out of 10, Exceptional, (43)
"Beautiful, relaxing stay at this home in Saugerties. We loved the private location yet very close to Woodstock and Saugerties. Nick’s communication was fantastic, responding quickly to our questions. Safe, easy, flexible check in and check out. Inside was mix of rustic cabin and modern appliances, super clean. 100% recommend to anyone. "
A-Frame of Mind
Tuscan Year Round Beauty - Pickleball Court
Outdoor dining

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (176)
"A beautiful, peaceful location to enjoy nature, yet be close enough to restaurants and shopping for convenience. We had four days of quiet and serenity in the warm, cozy, "feels like home" cottage. Our Labrador retriever loved exploring the woods and creekside (and barking at the wild turkeys!) Host Paul was attentive and gracious."
The Cabin at Chichester in the Catskills Mountains
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (23)
"The location was perfect—quiet, peaceful, and close to everything we wanted to do. The house was just as described: clean, comfortable, and well-equipped. We especially appreciated the cozy living room and the fully stocked kitchen, which made cooking meals a breeze. The beds were incredibly comfortable, and we slept soundly every night. The host was also very responsive and provided us with helpful tips about the area. Check-in and check-out were seamless, and we felt well taken care of...
The price is CA $95
CA $268 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Campfire Cottage: Fireplace, fire pit & no chores!
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Interior

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

9.8 out of 10, Exceptional, (19)
"Really love the mountains and fall leaves and lots to do and see in the area, unlike some resort towns. The accommodations were very nice, thank you! "
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Terrace/patio

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

10.0 out of 10, Exceptional, (22)
"Let me start off by saying Bernadette is a very attentive host, communication was great despite the fact that she was dealing with a family emergency during our trip. The location is exactly what my friends and I were after - an escape with no neighbors in sight, a place where we could cook, play cards, and gaze at the stars with minimal light pollution. All the amenities promised were there, all the utilities worked as expected, and the view was phenomenal. Be aware that the home has some...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (122)
"Our family had a fantastic stay. The house was perfect for kids, with plenty of space and a lovely atmosphere."
Beautiful new house 3/4 mile from Hunter Mountain
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Dining

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

9.0 out of 10, Wonderful, (18)
"What a great place! Tucked into the snow capped mountains with a cozy fireplace, what more can you ask for? Communication was A+++ ! We’d totally come back here! ♥️♥️♥️"
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Fridge, microwave, oven, stovetop

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Sexiest Lil Cabin in Saugerties, NY
Exterior

Sexiest Lil Cabin in Saugerties, NY

8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor dining

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

9.6 out of 10, Exceptional, (172)
"The property was fantastic. The check-in process was super easy, and the owners stopped by to walk us through the property and answer our questions. If you like using a sauna, then this is the place for you. If you like hot tubbing, then this is the place for you. If you want a wood burning fire place, then this is the place for you. I would absolutely recommend this property, and I will definitely stay again. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
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.
Don't see what you're looking for?
See all available properties in Woodstock
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Woodstock you may be interested in

Woodstock Way Hotel
Superior Room, Fireplace, River View

Woodstock Way Hotel

4.0 star property
9.6 out of 10, Exceptional, (127)
"Stay here when you go to Woodstock. "
The price is CA $481
CA $595 total
includes taxes & fees
Dec 23 - Dec 24
Woodstock Way Hotel
Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (226)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
Streamside Cottage Half Mile to Town of Woodstock
The Herwood Inn
Exterior detail

The Herwood Inn

4.5 star property
9.8 out of 10, Exceptional, (50)
"It’s was very lovely. Check in took me a moment to figure out but over all not too hard. The room I chose faced the street… which was too active more my preference but it wasn’t so bad. Woodstock is a quiet spot to begin with"
The price is CA $215
CA $241 total
includes taxes & fees
Jan 14 - Jan 15, 2025
The Herwood Inn
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.

Frequently asked questions

Are there vacation rentals in Woodstock?

Yes, there are vacation rentals in Woodstock close to Woodstock Music Shop, or you can choose a secluded option if you're looking for a relaxing stay. The forests and art scene are just a few reasons why tourists like Woodstock. Make sure you have time to check out the riverfront and mountain views during your trip.

What's the top vacation rental in Woodstock?

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace: This highly rated vacation home rental in Woodstock is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Woodstock?

Expedia has 59 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Overlook Mountain Trailhead and Catskill State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Woodstock Music Shop. Other places in town to visit include Woodstock Public Library and Woodstock Golf Club.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned properties you can reserve for several days or longer in Woodstock. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.