Stockbridge Holiday Rentals

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Check prices for these dates

Tonight
15 Dec - 16 Dec
Tomorrow
16 Dec - 17 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Stockbridge holiday rentals

Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cabin in Killington

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
Indoor pool
Mountain Green

Condo resort in Killington

Mountain Green
2.0 star property
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,734
HK$2,327 total
includes taxes & fees
16 Dec - 17 Dec
Mountain Green
Interior
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Condo in Killington

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
The price is HK$1,355
HK$3,263 total
includes taxes & fees
13 Jan - 14 Jan 2026
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Exterior
Cozy Loft for two with Hot Tub & Mtn Views

Cabin in Granville

Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (272)
"Very beautiful little cabin and very private we are definitely keeping this on are favorites list so we can stay again "
United States
Kevin B.
Cozy Loft for two with Hot Tub & Mtn Views
TV, fireplace, DVD player, books
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Cabin in Granville

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (530)
"We had such an amazing trip! We were able to ski Killington, Okemo and Stowe while staying there. The cabin was so cozy and the beds were very comfortable. The host was excellent and checked in to ensure everything was just perfect. The cabin is very charming and it was beautiful to watch the snow fall while sitting in front of the toasty fireplace. 1000 percent would stay again!!! Lots of love went in to making this cabin for sure. It truly felt magical for the week we were there."
United States
Brooke
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.4 out of 10, Exceptional, (3)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is HK$1,168
HK$1,500 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Condo in Killington

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is HK$974
HK$2,253 total
includes taxes & fees
16 Dec - 17 Dec
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Fireplace, books
Stetson Hollow Cabin by Stetson Brook

Cabin in Warren

Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
The price is HK$1,681
HK$3,400 total
includes taxes & fees
16 Dec - 17 Dec
Stetson Hollow Cabin by Stetson Brook
Indoor pool
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Condo in Killington

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
8.2 out of 10, Very good, (38)
"Room was constantly too hot. Otherwise a great stay"
United States
Cameron M.
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Exterior
Killington Retreat

Condo in Killington

Killington Retreat
2.0 star property
9.8 out of 10, Exceptional, (17)
"It was clean and check-in was simple. "
United States
David M.
Killington Retreat
Exterior
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

Holiday Home in killington

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
9.6 out of 10, Exceptional, (17)
"Great place to stay. Central location, bedrooms spacious and common areas w/plenty of space to hang out."
United States
Scott B.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Living area
Killington Sapphire

Condo in Killington

Killington Sapphire
9.4 out of 10, Exceptional, (8)
"Everything we needed to enjoy your family trip!"
United States
Kristen B.
Killington Sapphire
Smart TV, fireplace, books
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Holiday Home in Hartford

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
10.0 out of 10, Exceptional, (131)
"My sister and I stayed here while taking a two day class at King Arthur Baking School. The pictures don't even do it justice on how cute and well appointed the property is. The beds were very comfortable with nice linens and there were plenty of bath towels. The owners were always quick to respond to any question. We would definitely stay there again. "
United States
Stacy S.
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
Interior
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cabin in Cavendish

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
10.0 out of 10, Exceptional, (31)
"Very nice property. Full of extra touches (hot tub, virtual fireplace). I appreciated access to a laundry facility. Highly recommend this property."
United States
Julie C.
The price is HK$1,611
HK$2,711 total
includes taxes & fees
16 Dec - 17 Dec
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Property grounds
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Holiday Home in Chelsea

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, (38)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is HK$1,168
HK$1,500 total
includes taxes & fees
2 Jan - 3 Jan 2026
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Exterior
Secluded retreat in the trees

Cabin in Roxbury

Secluded retreat in the trees
10.0 out of 10, Exceptional, (37)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is HK$981
HK$1,831 total
includes taxes & fees
16 Dec - 17 Dec
Secluded retreat in the trees
TV, fireplace, DVD player, books
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Condo in Killington

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
United States
Shawn C.
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Fridge, microwave, oven, stovetop
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Holiday Home in Killington

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
Exterior
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Cottage in Ludlow

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (20)
"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
Property grounds
Treehouse at Wise Pines- SoBo

Cabin in Woodstock

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$1,168
HK$1,456 total
includes taxes & fees
16 Dec - 17 Dec
Treehouse at Wise Pines- SoBo
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

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

10/10 Excellent
"Great! "
Matthew 2-night trip
Posted 10 hours ago
Holiday Inn Express Hotel & Suites White River Junction by IHG

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.