Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Woodstock holiday homes

Interior

A charming 1820's farmhouse

A charming 1820's farmhouse
Woodstock
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful home. It was a good location for my family to attend a family wedding at the Woodstock Inn."
United States
Robin H.
The price is €1,261
includes taxes & fees
19 Jan - 20 Jan
A charming 1820's farmhouse
Exterior

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
2.0 star property
Randolph
10.0 out of 10, Exceptional, (1 review)
The price is €84
includes taxes & fees
17 Jan - 18 Jan
Off Grid Glamping Shed with River Access
Interior

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Killington
10.0 out of 10, Exceptional, (1 review)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is €303
includes taxes & fees
19 Jan - 20 Jan
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
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 €244
includes taxes & fees
19 Jan - 20 Jan
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, fireplace, DVD player, offices

Spa, Fireplace & Pet Friendly - Top of the Hill

Spa, Fireplace & Pet Friendly - Top of the Hill
Quechee
9.8 out of 10, Exceptional, (6 reviews)
"Appreciated the large outdoor deck area, grill, and plenty of space for the family to relax."
United States
Maryanne C.
The price is €516
includes taxes & fees
29 Jan - 30 Jan
Spa, Fireplace & Pet Friendly - Top of the Hill
Interior

180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
8.0 out of 10, Very good, (2 reviews)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is €624
includes taxes & fees
11 Feb - 12 Feb
180-degree panoramic views of Vermont's mountains from the living room and Deck
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is €533
includes taxes & fees
26 Jan - 27 Jan
Large Killington Area Home | Sleeps 7 | Game Room
Fridge, microwave, oven, stovetop

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, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is €372
includes taxes & fees
20 Jan - 21 Jan
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Property grounds

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
2.0 star property
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
3 bedrooms, desk, iron/ironing board, travel cot

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is €491
includes taxes & fees
21 Jan - 22 Jan
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
8.0 out of 10, Very good, (1 review)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is €415
includes taxes & fees
28 Jan - 29 Jan
Luxury Condo Tucked in the Heart of Killington
Exterior

Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.0 out of 10, Wonderful, (4 reviews)
"This place is a perfect rustic getaway with easy convenience to town. The host was great. Spacious and super relaxing with nice view out back. "
United States
Thaddeus T.
Killington Retreat | Deck-Fire Pit-Mountain Views!
Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is €575
includes taxes & fees
20 Jan - 21 Jan
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is €577
includes taxes & fees
20 Jan - 21 Jan
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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, (36 reviews)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is €549
includes taxes & fees
20 Jan - 21 Jan
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
2.0 star property
Mendon
10.0 out of 10, Exceptional, (1 review)
"Amazing stay! Gorgeous house, clean, perfect location. The host was super responsive and made the check in check out process so easy.Highly reccomend and can’t wait to stay again next year. "
United States
Nicole H.
The price is €597
includes taxes & fees
19 Jan - 20 Jan
large ski ranch hot tub close to killington pets ok
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (1 review)
The price is €389
includes taxes & fees
2 Feb - 3 Feb
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Exterior

Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.

Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm."
United States
Maria K.
The price is €532
includes taxes & fees
19 Jan - 20 Jan
Powder Park Place: Lower Unit. Cozy and close to the Mountain! 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, (84 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is €387
includes taxes & fees
20 Jan - 21 Jan
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is €946
includes taxes & fees
25 Jan - 26 Jan
Cozy Vermont Cabin · Mountain Views · Near Okemo
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Clean, quiet, good breakfast. Check in was easy and staff was friendly. "
Christopher 1-night trip
Posted 1 day ago
Align Inn Vermont

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
253
Accommodation
818 Holiday Homes
Lowest Price
€84
Highest Price
€1,261