Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge and around

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (2)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is €177
includes taxes & fees
26 Aug - 27 Aug
Sleep Woodstock - Dog Friendly King Suite

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is €146
includes taxes & fees
28 Aug - 29 Aug
Glamping hut with WiFi in Ripton, biking, hiking, skiing

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (2)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

Off Grid Glamping Shed with River Access

2.0 star property
The price is €84
includes taxes & fees
26 Aug - 27 Aug
Off Grid Glamping Shed with River Access

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (21)
"Pleasant hosts. My daughter milked s goat! Great night’s sleep."
The price is €168
includes taxes & fees
26 Aug - 27 Aug
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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

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

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

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

10.0 out of 10, Exceptional, (1)
"Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again."
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Acres & Views! Firepit, BBQ | Bayley Way Getaway

Acres & Views! Firepit, BBQ | Bayley Way Getaway

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is €447
includes taxes & fees
26 Aug - 27 Aug
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (38)
"Awsome place to stay for a week! "
Spacious country home, beautiful sunsets, 40 acres

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is €138
includes taxes & fees
26 Aug - 27 Aug
Two Queen Bed Standard Hotel room with outdoor heated pool 201

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite

Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

8.0 out of 10, Very good, (1)
"Place was nice a cozy. Had a minor issue that was communicated quickly and resolved."
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

9.2 out of 10, Wonderful, (5)
"Cute & functional 3 BR house. Was great for our spring skiing trip at Killington. "
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Deluxe One bedroom Queen Suite with outdoor heated pool 203

9.4 out of 10, Exceptional, (9)
"Condo was clean & well furnished. Only stayed one night after a visit to Quechee, Woodstock, and area."
The price is €150
includes taxes & fees
26 Aug - 27 Aug
Deluxe One bedroom Queen Suite with outdoor heated pool 203

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 208

9.4 out of 10, Exceptional, (17)
"The space was clean and comfortable, location is perfect and heated pool was great after a day on the slopes!"
The price is €170
includes taxes & fees
26 Aug - 27 Aug
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 208
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 Stockbridge Hotel Reviews