Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Woodstock holiday rentals

Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is HK$1,015
HK$1,191 total
includes taxes & fees
20 Jun - 21 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (11 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$1,175
HK$2,018 total
includes taxes & fees
24 Jun - 25 Jun
Addie's Place: A Quiet and Quirky Guesthouse
Terrace/patio

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, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,191
HK$2,483 total
includes taxes & fees
22 Jun - 23 Jun
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (19 reviews)
"We really enjoyed our stay! It was close to Okemo and it was so nice to relax in the hot tub after a day of skiing. We would definitely stay here again! "
United States
Dana C.
The price is HK$1,269
HK$2,307 total
includes taxes & fees
21 Jun - 22 Jun
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
South Royalton
The price is HK$1,861
HK$2,160 total
includes taxes & fees
21 Jun - 22 Jun
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
Interior

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, (39 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is HK$1,559
HK$2,676 total
includes taxes & fees
28 Jun - 29 Jun
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is HK$468
HK$1,612 total
includes taxes & fees
21 Jun - 22 Jun
Mountain Green
Smart TV, fireplace

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, (15 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is HK$1,114
HK$3,757 total
includes taxes & fees
18 Jun - 19 Jun
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (17 reviews)
"We wish there had been a recycle box. Also, mini split in living room didn’t work as well as the bedroom mini splits did for heat. Also, curtains/drapes on living room windows would be great and would help with heat loss."
United States
Jane
The price is HK$1,142
HK$3,467 total
includes taxes & fees
18 Jun - 19 Jun
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is HK$1,058
HK$3,843 total
includes taxes & fees
18 Jun - 19 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Property grounds

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, (111 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is HK$1,058
HK$2,628 total
includes taxes & fees
18 Jun - 19 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Bathroom

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The Suites at Killington Center
Exterior

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (23 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
The price is HK$3,384
HK$6,136 total
includes taxes & fees
21 Jun - 22 Jun
Charming Lakefront Cottage on Lake Mascoma
Shower, hair dryer, towels

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
9.0 out of 10, Wonderful, (6 reviews)
"Clean studio and very close to both Killington and Pico. Also very close to restaurants and bars. The kitchenette was a little small and had no range but otherwise this was a great place to stay for 2 ppl. Would stay here again."
United States
Karl F.
The price is HK$631
HK$2,060 total
includes taxes & fees
18 Jun - 19 Jun
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (86 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
The price is HK$1,175
HK$2,770 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Private kitchen

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 HK$909
HK$2,071 total
includes taxes & fees
21 Jun - 22 Jun
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Fridge, microwave, oven, stovetop

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is HK$1,029
HK$2,190 total
includes taxes & fees
23 Jun - 24 Jun
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Interior

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, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is HK$814
HK$1,233 total
includes taxes & fees
22 Jun - 23 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Indoor pool, a heated pool

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Killington
9.8 out of 10, Exceptional, (10 reviews)
"Great Location"
United States
Brian B.
The price is HK$953
HK$3,336 total
includes taxes & fees
18 Jun - 19 Jun
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
TV, fireplace, Netflix, streaming services

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
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

White River Inn and Suites

White River Inn and Suites

10/10 Excellent
"We stayed here when we attended a graduation at Darmouth recently. Our room was comfortable, spacious, and clean. We felt like we were in a home away from away from home so we were able to get good sleep and relaxation. We took advantage of the laundry facility which was easy to use. The breakfast was a standard hotel breakfast of eggs, sausages, waffles, breads, & pastries with coffee. It was a perfect start to the day & the lovely woman in charge of breakfast was amazingly friendly."
Jessica 2-night trip
Posted 4 hours ago
White River Inn and Suites

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 Red Wagon Toy Company, 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?

Historic Charm, Located On the River - Rustic Chic: This highly rated holiday home rental in Woodstock is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden. Another good choice for your trip to Woodstock is Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town.

How many holiday rentals are there in Woodstock?

Expedia has 33 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 Mount Tom Peak and Marsh-Billings-Rockefeller National Historical Park are a couple of picturesque spots to enjoy the outdoors. While here, Red Wagon Toy Company and Ottaquechee River 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.