Woodstock Holiday Rentals

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Our top choices for Woodstock holiday rentals

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (46 reviews)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
United States
Paul H.
The price is AU$465
includes taxes & fees
25 Jan - 26 Jan
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Woodstock
8.2 out of 10, Very good, (10 reviews)
"Great place. Great location "
United States
Anonymous traveller
The price is AU$439
includes taxes & fees
27 Jan - 28 Jan
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (7 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 AU$1,378
includes taxes & fees
22 Jan - 23 Jan
Woodstock Historic Artist Estate - The Museum House

Fall Foliage Getaway!

Fall Foliage Getaway!
Woodstock
10.0 out of 10, Exceptional, (12 reviews)
"We booked this home in August and the property owner has been accessible ever since! His home is perfect!! The bedrooms and bathrooms were perfect for.us and another couple to stay...kitchen had everything we needed! The home is a perfect distance from town as well as hiking trails and the outdoor firepit atea is a perfect way to unwind after a busy day exploring the area!We will def book this again!"
United States
Gina V.
The price is AU$1,075
includes taxes & fees
26 Jan - 27 Jan
Fall Foliage Getaway!

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
Woodstock
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 AU$517
includes taxes & fees
22 Jan - 23 Jan
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (281 reviews)
"Awesome place to stay!"
United States
Earl
The price is AU$208
includes taxes & fees
27 Jan - 28 Jan
Starlite Motel

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (134 reviews)
"I loved every single part of the stay "
United States
Srijana
The price is AU$272
includes taxes & fees
22 Jan - 23 Jan
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
Stone Ridge
9.0 out of 10, Wonderful, (15 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is AU$229
includes taxes & fees
22 Jan - 23 Jan
Cozy Apartment with Sauna in Historic Stone Ridge

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is AU$411
includes taxes & fees
3 Feb - 4 Feb
Retro Retreat: renovated 2BR, desk, no chore list!

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is AU$324
includes taxes & fees
1 Feb - 2 Feb
Charming loft cottage in tranquil Germantown with WiFi, AC

Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck
Rhinebeck Village
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is AU$349
includes taxes & fees
26 Jan - 27 Jan
Private Studio Close to Downtown Rhinebeck

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.6 out of 10, Exceptional, (27 reviews)
"Very clean very comfortable beds."
United States
Millgate F.
The price is AU$367
includes taxes & fees
22 Jan - 23 Jan
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$391
includes taxes & fees
26 Jan - 27 Jan
Campfire Cottage: Fireplace, fire pit & no chores!

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is AU$293
includes taxes & fees
22 Jan - 23 Jan
Mid-Century DJ’s Dream

The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (34 reviews)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is AU$404
includes taxes & fees
22 Jan - 23 Jan
The Studio at the Inn at High Falls

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (21 reviews)
"Perfect place for a visit to the Hudson Valley. Very comfortable and well taken care of. Friendly neighbors. 3 blocks from Downtown Catskill"
United States
Kirk N.
The price is AU$367
includes taxes & fees
22 Jan - 23 Jan
Charming Cottage in the Heart of Catskill & Pet Friendly

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (41 reviews)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is AU$236
includes taxes & fees
1 Feb - 2 Feb
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
10.0 out of 10, Exceptional, (3 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is AU$261
includes taxes & fees
25 Jan - 26 Jan
Jessie's Harvest House Suite

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.2 out of 10, Wonderful, (16 reviews)
"Beautiful location in a well kept property! Highly recommend it."
United States
Robert
The price is AU$403
includes taxes & fees
22 Jan - 23 Jan
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (13 reviews)
"Great spot!"
United States
Dylan
The price is AU$289
includes taxes & fees
22 Jan - 23 Jan
Country Cottage with beautiful views and easy access to Catskills activities.
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

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodstock holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as AU$208 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts : This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 The Comeau Property, or simply take in cultural attractions like SweetHeart Gallery and Colony. Other places in town to visit include Woodstock Music Shop and Catskill State Park.

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.