A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Woodstock Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Woodstock vacation rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
$278 nightly
The price is $303
Oct 27 - Oct 28
Total with taxes and fees
Fat Sheep Farm & Cabins
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
$241 nightly
The price is $270
Oct 28 - Oct 29
Total with taxes and fees
Bridgewater Living - Ben&Jerry Suite
A sunroom with wicker furniture, large windows, and string lights.

3. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (18 reviews)
"Perfect size and location! "
United States
Lyn H.
$220 nightly
The price is $249
Oct 28 - Oct 29
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
A compact kitchen with a refrigerator, stove, microwave, and sink.

4. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
$507 nightly
The price is $567
Sep 30 - Oct 1
Total with taxes and fees
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Dining

5. Gorgeous, clean studio in brand new building.

Gorgeous, clean studio in brand new building.
Hartford
$183 nightly
The price is $207
Oct 4 - Oct 5
Total with taxes and fees
Gorgeous, clean studio in brand new building.
A bedroom with two beds, a door, and a small table with a lamp.

6. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
$256 nightly
The price is $287
Sep 30 - Oct 1
Total with taxes and fees
Bridgewater Living - Ski VT Suite
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

7. 180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
$478 nightly
The price is $540
Sep 30 - Oct 1
Total with taxes and fees
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

8. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
$256 nightly
The price is $290
Sep 30 - Oct 1
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
A residential area with houses, a swimming pool, and a mountain backdrop.

9. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was great"
United States
Nathan H.
$236 nightly
The price is $267
Sep 30 - Oct 1
Total with taxes and fees
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A living room with a fireplace, a sofa, a coffee table, and a television.

10. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
$336 nightly
The price is $380
Sep 30 - Oct 1
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi
A wooden cabin with multiple balconies and a stone chimney.

11. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.2 out of 10, Wonderful, (59 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
$560 nightly
The price is $633
Sep 30 - Oct 1
Total with taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

12. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
$281 nightly
The price is $318
Sep 30 - Oct 1
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

13. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
$231 nightly
The price is $262
Sep 30 - Oct 1
Total with taxes and fees
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

14. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
$377 nightly
The price is $426
Oct 4 - Oct 5
Total with taxes and fees
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

15. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (54 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$375 nightly
The price is $404
Sep 30 - Oct 1
Total with taxes and fees
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Exterior

16. Clean, cozy, beautiful studio in the heart of WRJ.

Clean, cozy, beautiful studio in the heart of WRJ.
Hartford
$180 nightly
The price is $203
Oct 7 - Oct 8
Total with taxes and fees
Clean, cozy, beautiful studio in the heart of WRJ.
Aerial view

17. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$362 nightly
The price is $398
Oct 12 - Oct 13
Total with taxes and fees
The Suites at Killington Center
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

18. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
$247 nightly
The price is $279
Sep 30 - Oct 1
Total with taxes and fees
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

19. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$205 nightly
The price is $232
Oct 6 - Oct 7
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

20. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
$351 nightly
The price is $397
Sep 30 - Oct 1
Total with taxes and fees
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
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

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

10/10 Excellent
"Quiet, WiFi works, I don’t need anything else."
Jesse 1-night trip
Posted 20 hours ago
Super 8 by Wyndham White River Junction

Find out more about Woodstock

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $249 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation 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 vacation.

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 vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to Billings Farm and Museum, or you can choose a more remote option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your vacation.

What's the top vacation rental that Woodstock has to offer?

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated vacation home rental in Woodstock is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind. Another good choice for your trip to Woodstock is Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!.

How many vacation rentals are there in Woodstock?

Expedia has 37 vacation 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 Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Green Mountain National Forest are other places worth a visit.

What’s a vacation rental in Woodstock like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Woodstock. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.