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

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Woodstock holiday rentals

Exterior

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
The price is HK$1,871
HK$2,467 total
includes taxes & fees
1 Sept - 2 Sept
Fat Sheep Farm & Cabins
Aerial view

2. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is HK$612
HK$1,826 total
includes taxes & fees
11 Aug - 12 Aug
Mountain Green
Interior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.4 out of 10, Exceptional, (15 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is HK$1,177
HK$2,030 total
includes taxes & fees
11 Aug - 12 Aug
Addie's Place: A Quiet and Quirky Guesthouse
TV, fireplace, DVD player, books

4. 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.
The price is HK$527
HK$2,679 total
includes taxes & fees
11 Aug - 12 Aug
Resort condo with mountain views, full kitchen, and free WiFi
Terrace/patio

5. 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, (13 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,451
HK$2,846 total
includes taxes & fees
20 Aug - 21 Aug
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior

6. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (46 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
The price is HK$1,356
HK$2,811 total
includes taxes & fees
9 Aug - 10 Aug
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Smart TV, fireplace

7. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (19 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is HK$1,115
HK$3,763 total
includes taxes & fees
11 Aug - 12 Aug
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Beach

8. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is HK$2,188
HK$4,121 total
includes taxes & fees
9 Aug - 10 Aug
Cabin on the hill Ascutney Vt - 4 bedrooms
Dining

9. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is HK$855
HK$2,812 total
includes taxes & fees
10 Aug - 11 Aug
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Interior

10. 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (19 reviews)
"Would stay again!"
United States
Hannah M.
The price is HK$815
HK$1,235 total
includes taxes & fees
20 Aug - 21 Aug
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Exterior

11. 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
9.2 out of 10, Wonderful, (7 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.
The price is HK$632
HK$2,062 total
includes taxes & fees
11 Aug - 12 Aug
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Interior

12. Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
The price is HK$1,446
HK$4,235 total
includes taxes & fees
10 Aug - 11 Aug
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Terrace/patio

13. CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
9.8 out of 10, Exceptional, (26 reviews)
"Great trip!"
United States
casey d.
The price is HK$955
HK$2,151 total
includes taxes & fees
10 Aug - 11 Aug
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Property grounds

14. 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
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is HK$585
HK$2,079 total
includes taxes & fees
9 Aug - 10 Aug
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV

15. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is HK$1,441
HK$5,425 total
includes taxes & fees
25 Aug - 26 Aug
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Dining

16. Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is HK$942
HK$2,802 total
includes taxes & fees
9 Aug - 10 Aug
Killington resort: Walk to Mountain, Biking & Pool
Living area

17. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is HK$883
HK$2,664 total
includes taxes & fees
16 Aug - 17 Aug
Killington condo 5 min to killington resort
Interior

18. CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is HK$988
HK$2,136 total
includes taxes & fees
10 Aug - 11 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
Golf

19. BearNecessities- Pool, Hot Tub, Gym

BearNecessities- Pool, Hot Tub, Gym
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The unit was right across from Killington with many great amenities. The place was very cozy and perfect for a quick stay before a day of skiing."
United States
Matthew S.
The price is HK$971
HK$2,622 total
includes taxes & fees
18 Aug - 19 Aug
BearNecessities- Pool, Hot Tub, Gym
Smart TV

20. Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!

Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!
Killington
9.8 out of 10, Exceptional, (187 reviews)
"The condo was in excellent condition and very clean. Great location too. Owner was very responsive. "
United States
Michael V.
The price is HK$1,498
HK$1,932 total
includes taxes & fees
17 Aug - 18 Aug
Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & 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

The Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"proche des pentes"
Philippe 1-night trip
Posted 9 hours ago
The Mountain Inn at Killington

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 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?

Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!: This highly rated holiday home rental in Woodstock is located on a river, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Woodstock are Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town and Riverside Vista, Woodstock Riverfront House.

How many holiday rentals are there in Woodstock?

Expedia has 34 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. While here, VINS Nature Center and Saskadena Six Ski Area are other places worth a visit.

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.