Photo by Rachel Samanyi

Holiday Rentals in Woodstock

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Our top choices for Woodstock holiday rentals

A charming 1820's farmhouse

A charming 1820's farmhouse
Woodstock
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful home. It was a good location for my family to attend a family wedding at the Woodstock Inn."
United States
Robin H.
A charming 1820's farmhouse

Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse
Hartford
10.0 out of 10, Exceptional, (4 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is €166
includes taxes & fees
14 Jan - 15 Jan
Addie's Place: A Quiet and Quirky Private Guesthouse

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.8 out of 10, Exceptional, (14 reviews)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is €164
includes taxes & fees
14 Jan - 15 Jan
Treehouse at Wise Pines- NoBo

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.6 out of 10, Exceptional, (7 reviews)
The price is €168
includes taxes & fees
10 Feb - 11 Feb
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is €345
includes taxes & fees
27 Jan - 28 Jan
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is €279
includes taxes & fees
5 Feb - 6 Feb
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (2 reviews)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is €607
includes taxes & fees
14 Jan - 15 Jan
The Woods by Killington Vacation Rentals - 2 Bedrooms

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is €188
includes taxes & fees
19 Jan - 20 Jan
Vermont Suite | 10 Min to Killington & Woodstock

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is €247
includes taxes & fees
19 Jan - 20 Jan
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great property, as advertised."
United States
Chris A.
The price is €288
includes taxes & fees
15 Jan - 16 Jan
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
"Great !"
United States
Raul
The price is €252
includes taxes & fees
14 Jan - 15 Jan
Mountain Green

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (10 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
The price is €528
includes taxes & fees
15 Jan - 16 Jan
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is €619
includes taxes & fees
9 Feb - 10 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is €582
includes taxes & fees
10 Feb - 11 Feb
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (75 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €325
includes taxes & fees
19 Jan - 20 Jan
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64 reviews)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is €275
includes taxes & fees
15 Jan - 16 Jan
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo
3.5 star property
Killington
10.0 out of 10, Exceptional, (1 review)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
The price is €553
includes taxes & fees
14 Jan - 15 Jan
Fall Line Condo D4 2 Bedroom Condo

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is €274
includes taxes & fees
14 Jan - 15 Jan
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is €363
includes taxes & fees
14 Jan - 15 Jan
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (8 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is €287
includes taxes & fees
14 Jan - 15 Jan
Killington condo 5 min to killington resort
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, apart-hotels, 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 favorite 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 depends 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 €166 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your holiday.

What are some of the best holiday rentals that Woodstock has to offer?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This holiday home rental outside of Woodstock is located in the mountains, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware and a coffee maker. You can relax into your holiday with a garden and 1 hot tub.

How many holiday rentals are there in Woodstock?

Expedia has 28 holiday rentals for your stay in Woodstock.

What’s there to see and do in Woodstock?

Cultural attractions include Woodstock Town Hall Theatre and Billings Farm and Museum, whereas Marsh-Billings-Rockefeller National Historical Park and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Killington Resort and Okemo Mountain Resort.

What’s a holiday rental in Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.