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

Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Woodstock holiday homes

Interior

Winterfound Farm, Full Farmhouse & Barn for Groups

Winterfound Farm, Full Farmhouse & Barn for Groups
Woodstock
The price is AU$2,408
includes taxes & fees
20 July - 21 July
Winterfound Farm, Full Farmhouse & Barn for Groups
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
Property grounds

Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
The price is AU$670
includes taxes & fees
20 July - 21 July
Beautiful 3-bedroom house with AC in charming Bridgewater
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 AU$698
includes taxes & fees
19 July - 20 July
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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, (87 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
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Coffee/tea maker, fridge, microwave, oven

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, (113 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is AU$586
includes taxes & fees
21 July - 22 July
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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 AU$332
includes taxes & fees
20 July - 21 July
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$705
includes taxes & fees
10 Aug - 11 Aug
large ski ranch hot tub close to killington pets ok
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is AU$565
includes taxes & fees
22 July - 23 July
Okemo's Back Room - in the heart of the village on the shuttle route!
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (17 reviews)
"Second time we have stayed here. Amazing home, amazing location. The flow and design makes us happy "
United States
karyn r.
The price is AU$847
includes taxes & fees
18 July - 19 July
New Ludlow Village Home with Stunning Okemo Mountain View
TV

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AU$912
includes taxes & fees
20 July - 21 July
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Coffee/tea maker, fridge, microwave, oven

Feel the real VT! Lakes, hikes, a foodies delight!

Feel the real VT! Lakes, hikes, a foodies delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
The price is AU$878
includes taxes & fees
27 July - 28 July
Feel the real VT! Lakes, hikes, a foodies delight!
Property grounds

Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is AU$694
includes taxes & fees
19 July - 20 July
Modern Farm House…minutes to Okemo; 2 King beds!
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AU$1,009
includes taxes & fees
5 Aug - 6 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$1,016
includes taxes & fees
20 July - 21 July
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Smart TV, fireplace

The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall

The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall
Killington
9.2 out of 10, Wonderful, (49 reviews)
"One of the best vrbo to date thank you!!!"
United States
jim c.
The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall
TV, streaming services, music library, video library

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Microwave, oven, stovetop, dishwasher

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AU$1,032
includes taxes & fees
18 July - 19 July
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Smart TV, fireplace

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
The price is AU$917
includes taxes & fees
20 July - 21 July
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AU$864
includes taxes & fees
20 July - 21 July
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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

10/10 Excellent
"Good location. Small pool and no chairs around pool"
Petra 2-night trip
Posted 19 hours ago
The Mountain Inn at Killington

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
241
Accommodation
881 Holiday Homes
Lowest Price
AU$332
Highest Price
AU$2,408