Stockbridge Holiday Rentals

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Check prices for these dates

Tonight
29 Oct - 30 Oct
Tomorrow
30 Oct - 31 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Stockbridge

Indoor pool
Mountain Green
Mountain Green
2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,442
HK$1,935 total
includes taxes & fees
9 Nov - 10 Nov
Mountain Green
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Exterior
Cozy Loft for two with Hot Tub & Mtn Views
Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (265)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
United States
Melissa Anne R.
Cozy Loft for two with Hot Tub & Mtn Views
TV, fireplace, DVD player, books
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (520)
"Great location. Very cute cabin and it had everything you would need even plenty of wood for the fire pit. We will be staying at one of Jeff’s places again soon no doubt."
United States
Bryan C.
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Property grounds
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
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, (33)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is HK$932
HK$1,218 total
includes taxes & fees
1 Nov - 2 Nov
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
The price is HK$1,165
HK$1,496 total
includes taxes & fees
30 Oct - 31 Oct
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
2.0 out of 10, (1)
"DON'T STAY HERE! Not upfront about major construction. Common hallway leading to the condo, was all taped off for painting, no ceiling tiles, laundry room being painted and none of that was disclosed. Condo was dusty, walls dirty, couch was staging and uncomfortable. Bed was uncomfortable too. One shower did not work at all and the other one had a trickle, and was unusable. The fire place was not usable, and the patio was not as it was pictured. The worst part was the owner would not return...
United States
Corinne R.
The price is HK$615
HK$2,302 total
includes taxes & fees
3 Nov - 4 Nov
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Property grounds
Idyllic Lakefront House Suited Two Families
Idyllic Lakefront House Suited Two Families
9.6 out of 10, Exceptional, (171)
"We spent 11 nights at the house, everything was great."
United States
Brian C.
Idyllic Lakefront House Suited Two Families
Fireplace, books
Stetson Hollow Cabin by Stetson Brook
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (158)
"Close to everything - downtown Warren/Waitsfield, swimming, and biking trails. Perfect space for the weekend. "
United States
Elizabeth B.
The price is HK$1,678
HK$3,393 total
includes taxes & fees
3 Nov - 4 Nov
Stetson Hollow Cabin by Stetson Brook
Exterior
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
10.0 out of 10, Exceptional, (113)
"Clean and great location!"
United States
Alex P.
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (126)
"This place was quite simply brilliant. I stay with my wife and four kids. The kids range in age from 10-17 and we had a great stay exploring the Upper Valley area"
United Kingdom
Matthew C.
Beautifully renovated with fireplace and coffee bar
Property grounds
Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is HK$1,165
HK$1,453 total
includes taxes & fees
2 Nov - 3 Nov
Treehouse at Wise Pines- SoBo
Exterior
Killington Retreat
Killington Retreat
2.0 star property
9.6 out of 10, Exceptional, (14)
"Easy to check in/out. Clean condo, easy access to everything in the area. "
United States
Stefan C.
Killington Retreat
Fridge, microwave, oven, stovetop
Custom-built Tiny House on forested lot near Quechee
Custom-built Tiny House on forested lot near Quechee
9.8 out of 10, Exceptional, (62)
"Small and cozy"
United States
Suede R.
Custom-built Tiny House on forested lot near Quechee
Fridge, microwave, oven, stovetop
Amazing home on 90 acres - AC, fireplace & great mountain views
Amazing home on 90 acres - AC, fireplace & great mountain views
9.0 out of 10, Wonderful, (43)
"It was in the woods but close to shops also. It was peaceful. We loved the covered screened in porch."
United States
Cherry H.
Amazing home on 90 acres - AC, fireplace & great mountain views
Exterior
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (18)
"The house, its location, and dock are real nice. Would come here again."
United States
Wendy G.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior
Treehouse at Wise Pines- NoBo
Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
United States
Gabriela
The price is HK$1,165
HK$1,453 total
includes taxes & fees
2 Nov - 3 Nov
Treehouse at Wise Pines- NoBo
Fridge, microwave, oven, stovetop
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
9.8 out of 10, Exceptional, (60)
"Ski in/ Ski out Great locationJoel was very helpful and friendly. Really enjoyed our stay. "
United States
cynthia c.
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
9.4 out of 10, Exceptional, (124)
"Another fun time at this well located, well appointed home."
United States
Ronald L.
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Desk, free WiFi, bed sheets
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
9.0 out of 10, Wonderful, (61)
"Great location near mountain! Simple room but exactly as advertised. We've stayed multiple times due to the cleanliness and ease of the place.Spacious room is bigger than most hotels with the added benefit of privacy as a sole condo setup."
United States
Sal C.
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Cute Inn and was very convenient. Very friendly staff. Air. Conditioning worked well and bed was comfortable. I’d stay again. "
Susan 1-night trip
Posted 1 day ago
Align Inn Vermont

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in Stockbridge
  • Use the map to find apartments and other holiday homes in the Stockbridge neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last

Look no further and take a look at our great range of rental properties in Stockbridge!

Frequently asked questions

Are there holiday rentals in Stockbridge?

Yes, there are holiday rentals close to the most popular sights in Stockbridge, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Stockbridge is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Stockbridge?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Stockbridge stay.

What’s there to see and do in Stockbridge?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Les Newell Wildlife Management Area and Belcher Library are other places to visit while you're in town.

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.