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Our top choices for Woodstock vacation homes

A charming 1820's farmhouse

Woodstock
10.0 out of 10, Exceptional, (29)
"Excellent accommodations! One of the best VRBO’s I’ve ever stayed in. There were 5 women traveling together for a long weekend and Carmen’s place was just the ticket with our own bedrooms and en suite bathrooms. We had the entire place to ourselves and felt very spoiled."
United States
kelly f.
The price is AED 3,320
AED 5,379 total
includes taxes & fees
14 Dec - 15 Dec
A charming 1820's farmhouse

Off Grid Glamping Shed with River Access

2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
The price is AED 215
AED 344 total
includes taxes & fees
10 Dec - 11 Dec
Off Grid Glamping Shed with River Access

Charming Lakefront Cottage on Lake Mascoma

Enfield
10.0 out of 10, Exceptional, (19)
"This is a beautiful lake house and it is super clean and the space is lovely and inviting. Lots to do in Hanover and surrounding Vermont towns - would absolutely stay with this host again!"
United States
Dian G.
The price is AED 1,010
AED 2,148 total
includes taxes & fees
13 Dec - 14 Dec
Charming Lakefront Cottage on Lake Mascoma

Mountain Stay | Skiing | Hiking | Sleeps 8

Bridgewater
9.6 out of 10, Exceptional, (7)
"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 AED 698
AED 1,983 total
includes taxes & fees
10 Dec - 11 Dec
Mountain Stay | Skiing | Hiking | Sleeps 8

Charming Cavendish Guesthouse

Cavendish
9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
The price is AED 651
AED 1,112 total
includes taxes & fees
10 Dec - 11 Dec
Charming Cavendish Guesthouse

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish
9.6 out of 10, Exceptional, (4)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
The Dorothy-10 minutes from Okemo- freshly renovated

Luxury Condo Tucked in the Heart of Killington

Killington
8.0 out of 10, Very Good, (1)
"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 AED 436
AED 1,201 total
includes taxes & fees
10 Dec - 11 Dec
Luxury Condo Tucked in the Heart of Killington

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

Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is AED 512
AED 1,812 total
includes taxes & fees
10 Dec - 11 Dec
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is AED 632
AED 1,966 total
includes taxes & fees
10 Dec - 11 Dec
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
The price is AED 1,238
AED 2,170 total
includes taxes & fees
18 Dec - 19 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Pomfret
10.0 out of 10, Exceptional, (4)
"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."
United States
Dee Dee H.
The price is AED 735
AED 1,633 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"This was a perfect property for our quick vacation. The house is very well equipped and you have everything you need for a relaxing fun stay in Killington. The hot tub was great, and the house is in a very convenient location while fairly private at the same time. We really enjoyed our stay and would definitely recommend staying here."
United States
Linda D.
The price is AED 735
AED 2,366 total
includes taxes & fees
10 Dec - 11 Dec
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

large ski ranch hot tub close to killington pets ok

2.0 star property
Mendon
10.0 out of 10, Exceptional, (1)
"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 AED 752
AED 1,879 total
includes taxes & fees
10 Dec - 11 Dec
large ski ranch hot tub close to killington pets ok

Whitetail Chalet at Killington: 4BR/2BA

2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"A beautiful property which is very well equipped and really well kept. Great communication and wish we could have stayed longer. "
United Kingdom
John P.
The price is AED 707
AED 2,458 total
includes taxes & fees
10 Dec - 11 Dec
Whitetail Chalet at Killington: 4BR/2BA

Breakaway House by Killington Vacation Rentals

2.0 star property
Killington
The price is AED 733
AED 2,665 total
includes taxes & fees
16 Dec - 17 Dec
Breakaway House by Killington Vacation Rentals

4BR Killington Home Perfect for Families, Pet-Friendly

2.0 star property
North Sherburne
10.0 out of 10, Exceptional, (22)
"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."
United States
Darko G.
The price is AED 727
AED 2,475 total
includes taxes & fees
10 Dec - 11 Dec
4BR Killington Home Perfect for Families, Pet-Friendly

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

Killington
10.0 out of 10, Exceptional, (1)
"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 AED 583
AED 1,356 total
includes taxes & fees
16 Dec - 17 Dec
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Ski home/Pool Table Mountain Views near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
Ski home/Pool Table Mountain Views near Killington/Woodstock

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

granville
9.4 out of 10, Exceptional, (83)
"Great place! Comfortable and conveniently located. "
United States
Violet R.
The price is AED 413
AED 1,220 total
includes taxes & fees
10 Dec - 11 Dec
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

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

Ludlow
9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AED 1,238
AED 2,170 total
includes taxes & fees
18 Dec - 19 Dec
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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