Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Woodstock holiday rentals

Smart TV, books

Apartment in Woodstock

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
10.0 out of 10, Exceptional, (11 reviews)
"In the heart of woodstock, walking distance to any of the shops and restaurants, even grocery stores!! For the low price, it was a great place to stay, great quiet area and felt so safe!"
United States
Eden C.
The price is HK$822
HK$2,191 total
includes taxes & fees
30 Mar - 31 Mar
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
WiFi, bed sheets

Apartment in Woodstock

Botanical Studio Retreat in the Heart of Woodstock
The price is HK$731
HK$2,151 total
includes taxes & fees
23 Mar - 24 Mar
Botanical Studio Retreat in the Heart of Woodstock
Terrace/patio

Cottage in woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.0 out of 10, Wonderful, (46 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is HK$1,409
HK$2,419 total
includes taxes & fees
15 Mar - 16 Mar
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

Holiday Home in Woodstock

Fall Foliage Getaway!
10.0 out of 10, Exceptional, (12 reviews)
"We loved the place - beautiful house and setting."
United States
Michele P.
The price is HK$2,528
HK$5,741 total
includes taxes & fees
14 Mar - 15 Mar
Fall Foliage Getaway!
1 bedroom, WiFi, bed sheets

Apartment in Woodstock

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
8.2 out of 10, Very good, (10 reviews)
"Great location !"
United States
greg h.
The price is HK$781
HK$2,260 total
includes taxes & fees
24 Mar - 25 Mar
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Private kitchen

Apartment in Woodstock

Beautiful Top Floor Unit in Downtown Woodstock!
8.0 out of 10, Very good, (1 review)
"Host was great, quick responses to my questions "
United States
Eben B.
The price is HK$820
HK$2,277 total
includes taxes & fees
19 Mar - 20 Mar
Beautiful Top Floor Unit in Downtown Woodstock!
Interior

Holiday Home in Woodstock

Woodstock Historic Artist Estate - The Museum House
9.8 out of 10, Exceptional, (9 reviews)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is HK$4,289
HK$7,494 total
includes taxes & fees
15 Mar - 16 Mar
Woodstock Historic Artist Estate - The Museum House
View from property

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (171 reviews)
"I just love this place, this was my second time and ofc I will be back"
United States
JANYRA
The price is HK$792
HK$1,193 total
includes taxes & fees
17 Mar - 18 Mar
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
1 bedroom, free WiFi, bed sheets

Holiday Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very good, (34 reviews)
"The location and layout cozy and warm. The odor of the water and bathroom like sulfer.Coffee seemed old pot did not work right.Could not get hot water for a shower either."
United States
dianna i.
The price is HK$880
HK$2,099 total
includes taxes & fees
17 Mar - 18 Mar
The Studio at the Inn at High Falls
Interior

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is HK$853
HK$1,656 total
includes taxes & fees
17 Mar - 18 Mar
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds

Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$696
HK$1,877 total
includes taxes & fees
16 Mar - 17 Mar
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Exterior

Cabin in Saugerties

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.0 out of 10, Very good, (47 reviews)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is HK$978
HK$1,271 total
includes taxes & fees
15 Mar - 16 Mar
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds

Cabin in Phoenicia

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
The price is HK$1,127
HK$2,226 total
includes taxes & fees
15 Mar - 16 Mar
"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Smart TV

Apartment in Kingston

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
9.6 out of 10, Exceptional, (25 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is HK$704
HK$1,797 total
includes taxes & fees
17 Mar - 18 Mar
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Interior

Apartment in Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
9.0 out of 10, Wonderful, (15 reviews)
"Cozy, clean, and extremely accommodating. Everything was planned out well and the sauna was lovely in such cold weather! Would highly recommend for anyone considering travel to this beautiful region of New York!"
United States
Avi
The price is HK$360
HK$1,122 total
includes taxes & fees
15 Mar - 16 Mar
Cozy Apartment with Sauna in Historic Stone Ridge
Interior

Holiday Home in West Kill

West Kill Barnhouse: Ski, Work & Unwind
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is HK$743
HK$2,764 total
includes taxes & fees
23 Mar - 24 Mar
West Kill Barnhouse: Ski, Work & Unwind
Smart TV, fireplace

Cabin in High Falls

Mossy Moody Cabin in High Falls, NY
9.8 out of 10, Exceptional, (18 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
The price is HK$1,448
HK$3,392 total
includes taxes & fees
12 Apr - 13 Apr
Mossy Moody Cabin in High Falls, NY
Terrace/patio

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (16 reviews)
"We stayed 2 nights with our dog. The cottage had everything we needed for our stay. "
United States
Debra S.
Country Cottage with beautiful views and easy access to Catskills activities.
Fridge, microwave, oven, stovetop

Holiday Home in Kingston

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is HK$509
HK$1,841 total
includes taxes & fees
24 Mar - 25 Mar
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Property grounds

Cabin in Palenville

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
10.0 out of 10, Exceptional, (29 reviews)
"Best place ever!!"
United States
LaurapatOsterwald S.
The price is HK$1,585
HK$2,886 total
includes taxes & fees
17 Mar - 18 Mar
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
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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Top Woodstock Hotel Reviews

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"Although the pool was closed everything rlse was great"
Amy 1-night trip
Posted 3 hours ago
Best Western Plus Kingston Hotel And Conference Center

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

Look no further and take a look at our great range of rental properties in Woodstock!

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals close to the most popular sights in Woodstock, 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?

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside of Woodstock is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Woodstock?

Expedia has 69 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Enjoy the outdoors at Overlook Mountain Trailhead and Thorn Preserve - Catskill Center, or simply take in cultural attractions like Colony and SweetHeart Gallery. Other places in town to visit include Woodstock Music Shop and Karma Triyana Dharmachakra Monastery.

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.