Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of Woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (41)
"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 €268
includes taxes & fees
9 Mar - 10 Mar
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

10.0 out of 10, Exceptional, (172)
"This was an incredible place to stay for a snowy weekend with the family. The house is huge and and just beautiful. The hosts even had the long driveway plowed and stairs/walkway shoveled for us, would definitely recommend staying here. "
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (90)
"This Woodstock gem is a lovely and spacious getaway spot. We had plenty of room for two couples and our dogs to stay comfortably for multiple days. The house is very close to downtown Woodstock and has all of the amenities you could need. We particularly enjoyed the ping-pong table, fireplace, and hot tub. Additionally the host is responsive and cares about you having a comfortable stay. We would definitely stay here again!"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

10.0 out of 10, Exceptional, (77)
"This was perfect place to spend time with friends!"
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is €180
includes taxes & fees
11 Mar - 12 Mar
Postcard Cabins Eastern Catskills

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (250)
"Works great for our family of seven to Ski at Belleayre Mountain resort. Thank you. "
The price is €138
includes taxes & fees
12 Mar - 13 Mar
Starlite Motel

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (39)
"The property was well maintained and a great space. The views along side the creek were amazing. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is €217
includes taxes & fees
6 Mar - 7 Mar
Esopus Creek modern Tiny house Retreat!

A-Frame of Mind

10.0 out of 10, Exceptional, (49)
"Fantastic location, excellent communication with Nick, cozy and well stocked with necessary supplies, very clean and quiet. Much needed vacation."
A-Frame of Mind

True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

2.0 star property
10.0 out of 10, Exceptional, (31)
"The place is perfect for skiing at Hunter. Highly recommend. "
The price is €239
includes taxes & fees
25 Mar - 26 Mar
True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

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

9.2 out of 10, Wonderful, (20)
"The property is beautiful. The soft snow blanketing the area only made it more so. Everything was exactly where it was said to be and our hosts were ready and willing to help at a moments notice. Couldn't ask for a better place"
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (8)
"My family and I had a lovely stay! The home is beautiful and comfortable with all the amenities that we needed, including a crib as we were traveling with a newborn. Not much in the immediate vicinity but a short drive to Kingston. Smooth communication and easy checkin/checkout process."
The price is €307
includes taxes & fees
5 Mar - 6 Mar
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (101)
"Nataliya was extremely responsive and considerate "
The price is €542
includes taxes & fees
1 Apr - 2 Apr
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.2 out of 10, Wonderful, (39)
"Easy and convenient, would stay again. "
The price is €176
includes taxes & fees
1 Apr - 2 Apr
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (30)
"When i tell you everything was as pictured! And thats rare, everything was perfect. Im so happy we chose to stay at Lily Cottage. Host was awesome, very helpful and even left a welcome snack...yum ! Thinking i may be back in the summer. PERFECT COUPLE GETAWAY!!"
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (28)
"Perfect location, we were there for a tour of CIA but it was an ideal location for exploring the area. Loved Rhinebeck Village! Owner was awesome, would stay again."
The price is €172
includes taxes & fees
12 Mar - 13 Mar
Mid-Century DJ’s Dream

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

The Farm at Hyde Park

9.8 out of 10, Exceptional, (65)
"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
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 types of properties in Woodstock you may be interested in

Woodstock Way Hotel

4.0 star property
9.4 out of 10, Exceptional, (142)
"Really cute tucked away area and also incredibly close to the town of Woodstock with all of its shops and restaurants so you don't need to drive once you're here. I loved the simple design of the rooms as well as their pet friendly options and small coffee shop that has a full coffee bar and snacks for guests. Staff working there were also incredibly sweet. I would suggest a few updates: -shower pressure was not great (it may have just been my room!) and having blankets for use on the couch...
The price is €321
includes taxes & fees
6 Mar - 7 Mar
Woodstock Way Hotel

Twin Gables of Woodstock

3.0 star property
9.8 out of 10, Exceptional, (141)
"Great room in a charming property "
The price is €159
includes taxes & fees
10 Mar - 11 Mar
Twin Gables of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of 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.

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Woodstock Music Shop, or you can select a more 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 are some of the best holiday rentals that Woodstock has to offer?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Woodstock is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Expedia has 62 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Overlook Mountain Trailhead and Thorn Preserve - Catskill Center 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 Catskill State Park and Woodstock Golf Club.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.