Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (464)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"Jeff is a very gracious host and kept in communication throughout this VRBO experience. The cabin is a wonderfully enchanting place with a lot of privacy, and everything you need to make your time spent there a very relaxing and rewarding experience. The cabin is within 20 minutes of Stowe, Vt. The culture is downhome and the food is great!!!!"
Cozy Loft for two with Hot Tub
Cozy Studio for 4 - Walk to Mountain w/ Balcony
8.8 out of 10, Excellent, (16)
"We traveled for the Killington Spartan race and this lodging met our needs perfectly. It’s was conveniently located directly across from the shuttle pick up. Also we were able to walk to a nearby restaurant for a delicious dinner. The condo was very clean and had everything we needed. Lars communicated frequently with everything we needed to know. I would definitely stay again! "
The price is AU$292
includes taxes & fees
30 Sept - 1 Oct
Cozy Studio for 4 - Walk to Mountain w/ Balcony
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
9.2 out of 10, Wonderful, (16)
"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (130)
"Lovely rental as always. Great location with opportunity to enjoy local highlights."
The price is AU$690
includes taxes & fees
1 Oct - 2 Oct
Stetson Hollow Cabin by Stetson Brook
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (74)
"Nice decor, a lot of personal touches and thought put into making the stay here very nice. Id totally stay here again or refer others to stay here. Quiet and removed but very close to town, nature hikes, and quaint eateries and gift shops."
Beautifully renovated with fireplace and coffee bar
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (190)
"The cabin was super cute and cozy! It was very clean and well kept. It was a little bit off the main road, but far enough back so the noise from the traffic wasn't too bad. There's also train tracks behind. We only saw one train, but it wasn't long and not too noisy. The loft space was a little tight, especially if you're on the taller side, but the bed was super comfy! There were many appliances and utensils in the kitchen and the hot tub was just awesome after a long day of hiking! Thank you...
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (157)
"My family and I went to Vermont for a Spartan Race and family vacation. The property was in a great location, close to the race. The host, John, was so responsive and helpful throughout our whole stay. John’s place is incredibly clean and has all the amenities you could want in your stay. I would highly recommend John’s place to anyone and plan to go back in the future. Thanks again for your hospitality John!"
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (33)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (151)
"Beautiful lake, kayaking, backyard firepit, hiking , such a fun area with a lot to explore.nearby, "
Idyllic Lakefront House Suited Two Families
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (198)
"We had a great and restful stay. The house was exactly as listed. Views were great with ducks, beaver and a family of deer. Good fishing from the dock. This is in my top 3 of all places at which we have stayed! Definitely recommended!!!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, (38)
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
The price is AU$257
includes taxes & fees
30 Sept - 1 Oct
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (15)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is AU$270
includes taxes & fees
23 Oct - 24 Oct
Treehouse at Wise Pines- SoBo
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, (11)
"The condo exceeded my expectations - it was clean and well-equipped and everything was in great condition. One of the beds is very firm and the other is pretty soft. We enjoyed the pool. Would definitely come back!"
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
10.0 out of 10, Exceptional, (42)
"We attended a wedding in Goshen. It was a ten minute drive. It worked out perfectly. The home is very clean and comfortable! The host even turned the porch light on for us for our late night return. "
The price is AU$325
includes taxes & fees
14 Oct - 15 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
9.0 out of 10, Wonderful, (16)
"Wonderful location on Lake Rescue. House is spacious with great views. High end finishes. Beds and linens were very comfortable. Kitchen has plenty of dishes, pots and pans. No keurig but we brought our own. Management was pretty responsive when we realized there was no remote for the firestick and they dropped one off the next day. There is only one tv for the entire house and it's in the basement.For a house that size, this is odd. But, we were there to fish, kyack and spend time together so...
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
9.8 out of 10, Exceptional, (30)
"Had a nice summer kickoff weekend with a few friends and their families. House had all the necessities and was a great layout for group meals and fire pit action."
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Amazing Mountain Condo - Right across the street to Killington Resort
9.8 out of 10, Exceptional, (165)
"Great location and very clean. You can walk to Snowshed or Ramshead Lodges. Nathan was great and very communicative. I would highly recommend."
Amazing Mountain Condo - Right across the street to Killington Resort
Custom-built Tiny House on forested lot near Quechee
10.0 out of 10, Exceptional, (45)
"The tiny house had everything I needed. I was in the area visiting family so I was out a lot but if you plan to stay in there is enough here to keep you busy. Centrally located to the highways and fun activities. Arturo was a wonderful host .we were in contact (not for any problems or issues) and he always responded promptly . You will enjoy your stay here. to keep you busyto keep ywonderful"
Custom-built Tiny House on forested lot near Quechee
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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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Other types of properties in Stockbridge you may be interested in

Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, (1004)
"Area is nice. Food options within walking distance. Staff were very nice. Hotel was clean but dated. Its probably the best option for the area. "
The price is AU$190
includes taxes & fees
20 Oct - 21 Oct
Comfort Inn Trolley Square
White River Inn and Suites
2.5 star property
7.2 out of 10, Good, (1000)
"Very pleasant staff."
The price is AU$320
includes taxes & fees
29 Sept - 30 Sept
White River Inn and Suites
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, (1000)
"The mountain lodge inn was a wonderful place to visit. Our room was on the 2nd floor and we had a fantastic view of the golf course, hill side and hot tub. The staff was very friendly and helpful. We’d stay there again any time. "
The price is AU$271
includes taxes & fees
28 Oct - 29 Oct
Killington Mountain Lodge, Tapestry Collection by Hilton
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.

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 12 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 Gifford Woods State Park. Green Mountain National Golf Course and Appalachian Trail Adventures are a couple of places you'll find in the wider area.

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.