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, (227)
"OVERALL, EVERYTHING WAS FANTASTIC. IF I WANTED TO BE REAL PICKY...THE KITCHEN WAS SMALL EVENTHOUGH IT HAD ALMOST EVERYTHING AND THE TV WAS IN THE LIVINGROOM ONLY, NONE IN THE BEDROOM. WE WOLD DEFINATELY STAY THERE AGAIN."
Streamside Cottage Half Mile to Town of Woodstock

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 €277
includes taxes & fees
9 Feb - 10 Feb
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!

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (247)
"Cozy,excellent cable package…"
The price is €138
includes taxes & fees
3 Feb - 4 Feb
Starlite Motel

Postcard Cabins Eastern Catskills

2.0 star property
7.4 out of 10, Good, (3)
"This tiny cabin was a dream. It has everything you need for a cozy, nature getaway. "
The price is €104
includes taxes & fees
4 Feb - 5 Feb
Postcard Cabins Eastern Catskills

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

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

2.0 star property
9.8 out of 10, Exceptional, (28)
"Great place and location. We have been staying at different condo places for the past 3 Winter Ski season. This is by far the best. Matt is great. "
The price is €269
includes taxes & fees
4 Feb - 5 Feb
True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (26)
"My daughter needed a place to stay while visiting for the holiday. Kevin was easy to reach and responded quickly. The apartment is very cute and was the perfect size. Everything was clean and had some nice personal touches. Im sure a summertime stay would be lovely, when the garden is in bloom"
The price is €158
includes taxes & fees
5 Feb - 6 Feb
Mid-Century DJ’s Dream

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 €224
includes taxes & fees
3 Feb - 4 Feb
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (13)
"Great property overlooking Hudson River. Close to Woodstock and Rheinbeck. Very good local restaurants for brunch and dinner. Host was great and responded quickly with all questions "
Hamptons on the Hudson in South Saugerties

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (38)
"Beautiful setting with this home. Kitchen appliances and amenities were great. Bedrooms slightly sparse, but very functional. Bathrooms clean and seemed to be recently updated. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

A-Frame of Mind

10.0 out of 10, Exceptional, (47)
"This place is Beautiful and very comfortable. They have all the amenities you could need. A few minutes from town, groceries and more. Private and quiet area. 20 minutes from Hunter Mountain. I would recommend to everyone. "
A-Frame of Mind

Hudson River Way by Woodstock Way Hotel

5.0 star property
The price is €351
includes taxes & fees
17 Feb - 18 Feb
Hudson River Way by Woodstock Way Hotel

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

10.0 out of 10, Exceptional, (213)
"Excellent communication. Cozy home. Really enjoyed our stay. "
The price is €779
includes taxes & fees
4 Feb - 5 Feb
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

9.4 out of 10, Exceptional, (3)
"Very nice."
The price is €475
includes taxes & fees
3 Feb - 4 Feb
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.6 out of 10, Exceptional, (20)
"David the host was prompt in responses and very helpful and kind. It was a beautiful cabin and we fully intend to come back. Thank you so much David. Please stay with confidence, thst it will be great experience "
The price is €318
includes taxes & fees
3 Feb - 4 Feb
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

10.0 out of 10, Exceptional, (12)
"Everything was wonderful."
The price is €731
includes taxes & fees
3 Feb - 4 Feb
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
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, (139)
"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 €325
includes taxes & fees
3 Feb - 4 Feb
Woodstock Way Hotel

The Herwood Inn

4.5 star property
9.8 out of 10, Exceptional, (55)
"A beautiful little bungalow retreat for an escape with my fiance! Love the distance to downtown & many shops and places to eat. Will absolutely be back. The host was out of this world awesome!"
The price is €166
includes taxes & fees
4 Feb - 5 Feb
The Herwood Inn

Twin Gables of Woodstock

2.5 star property
9.8 out of 10, Exceptional, (136)
" In love with this hotel in the heart of Woodstock!!! :) . The host LeAnn was absolutely amazing, friendly and super cool and sweet with my son Dante :) . The hotel is beautiful warm and at the same time funky design. The room was clean , modern and super comfortable. "
The price is €161
includes taxes & fees
4 Feb - 5 Feb
Twin Gables 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?

The Farm at Hyde Park: This holiday home rental outside Woodstock is located in a rural location, and has a fireplace, a patio and a BBQ 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 games.

How many holiday rentals are there in Woodstock?

Expedia has 61 holiday 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 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.