Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Woodstock vacation rentals

Interior

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is ￥46,299
￥107,828 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Iron/ironing board, WiFi, bed sheets

Beautiful Village of Woodstock home near the Inn

Beautiful Village of Woodstock home near the Inn
Woodstock
The price is ￥54,760
￥70,719 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Village of Woodstock home near the Inn
Fridge, microwave, oven, stovetop

Charming King Loft in Downtown Woodstock

Charming King Loft in Downtown Woodstock
Woodstock
10.0 out of 10, Exceptional, (6 reviews)
"A very charming space in the perfect location for downtown convenience!"
United States
Alex M.
The price is ￥50,290
￥77,394 total
includes taxes & fees
Jun 5 - Jun 6
Charming King Loft in Downtown Woodstock
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 ￥20,641
￥24,209 total
includes taxes & fees
Jun 9 - Jun 10
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
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, (18 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 ￥25,145
￥46,216 total
includes taxes & fees
Jun 3 - Jun 4
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (10 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is ￥23,948
￥41,313 total
includes taxes & fees
Jun 24 - Jun 25
Addie's Place: A Quiet and Quirky Guesthouse
Property grounds

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 ￥11,786
￥29,613 total
includes taxes & fees
Jun 3 - Jun 4
Vermont Suite | 10 Min to Killington & Woodstock
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, (11 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is ￥20,475
￥46,356 total
includes taxes & fees
Jun 3 - Jun 4
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
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 ￥24,027
￥71,168 total
includes taxes & fees
Jun 3 - Jun 4
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
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 ￥37,933
￥44,012 total
includes taxes & fees
Jun 12 - Jun 13
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
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, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is ￥21,553
￥53,561 total
includes taxes & fees
Jun 3 - Jun 4
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 ￥20,595
￥44,523 total
includes taxes & fees
Jun 3 - Jun 4
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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, (108 reviews)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is ￥21,553
￥53,561 total
includes taxes & fees
Jun 3 - Jun 4
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is ￥44,542
￥82,609 total
includes taxes & fees
Jun 5 - Jun 6
Cabin on the hill Ascutney Vt - 4 bedrooms
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, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is ￥28,019
￥85,740 total
includes taxes & fees
Jun 7 - Jun 8
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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 ￥16,556
￥25,071 total
includes taxes & fees
Jun 9 - Jun 10
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is ￥29,312
￥122,495 total
includes taxes & fees
Jun 3 - Jun 4
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Hair dryer, towels, soap, shampoo

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is ￥35,836
￥96,505 total
includes taxes & fees
Jun 3 - Jun 4
Terrific 3-bedroom cottage with AC in charming Cavendish
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is ￥12,213
￥30,186 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Rutland Retreat
Interior

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 ￥29,993
￥89,563 total
includes taxes & fees
Jun 3 - Jun 4
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
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

Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Have been staying here for years, and are not gonna stop! Lots of character & charm, clean & comfy rooms, & pleasant & helpful staff."
Gary B 1-night trip
Posted 2 hours ago
Hotel Coolidge

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:

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Frequently asked questions

Are there vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to Red Wagon Toy Company, 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?

Historic Charm, Located On the River - Rustic Chic: This highly rated vacation home rental in Woodstock is located on a river and has a fireplace, a balcony, and a barbecue grill 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 vacation with amenities like 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 vacation rentals are there in Woodstock?

Expedia has 33 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 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 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.