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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Woodstock holiday homes

Property grounds

1. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is €452
includes taxes & fees
2 Sept - 3 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
Room

2. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €248
includes taxes & fees
2 Sept - 3 Sept
Luxury Condo Tucked in the Heart of Killington
Living area

3. Quechee Club Home w/ Game Room

Quechee Club Home w/ Game Room
Hartford
The price is €787
includes taxes & fees
15 Sept - 16 Sept
Quechee Club Home w/ Game Room
Living area

4. 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.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Living area

5. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
2.0 star property
Killington
The price is €415
includes taxes & fees
2 Sept - 3 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Interior

6. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, 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 €239
includes taxes & fees
2 Sept - 3 Sept
CozyDen - AC, Bike to Mountain, Porch!
Interior

7. 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
9.0 out of 10, Wonderful, (7 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.
180-degree panoramic views of Vermont's mountains from the living room and Deck
Exterior

8. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Killington
9.6 out of 10, Exceptional, (70 reviews)
"Great stay. Killer location!"
United States
Matthew P.
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Living area

9. 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.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Living area

10. 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 €432
includes taxes & fees
2 Sept - 3 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Private kitchen

11. 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 €205
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Living area

12. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
House, 6 Bedrooms | Living area

13. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is €647
includes taxes & fees
2 Sept - 3 Sept
Breakaway House by Killington Vacation Rentals
Property grounds

14. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
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.
The price is €540
includes taxes & fees
2 Sept - 3 Sept
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Living area

15. 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, (51 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
Living area

16. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
The price is €745
includes taxes & fees
11 Sept - 12 Sept
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Living area

17. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is €163
includes taxes & fees
29 Sept - 30 Sept
Cozy Rutland Retreat
Living area

18. 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 €576
includes taxes & fees
2 Sept - 3 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
Living area

19. HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
The price is €451
includes taxes & fees
2 Sept - 3 Sept
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Terrace/patio

20. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. 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

On The River Inn

On The River Inn

10/10 Excellent
"We had a wonderful stay at On the River. The room was large, clean, and very quiet. It's a short, quick drive into town. The staff was pleasant and helpful. A good choice when staying near Woodstock."
Marc 1-night trip
Posted 1 hour ago
On The River Inn

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
295
Accommodation
868 Holiday Homes
Lowest Price
€163
Highest Price
€745