Stockbridge Vacation Rentals

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Vacation Rentals in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (44)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (248)
"Would definetly go back. Enjoyable, quiet, just an enjoyable stay!"
Cozy Loft for two with Hot Tub & Mtn Views

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a private deck, firepit, and dock

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (17)
"Loved this property. Was clean, well maintained, and cozy. My partner loved the size and the full kitchen. Was a good distance from Ludlow downtown, not too far. "
The price is CA $240
CA $426 total
includes taxes & fees
Jul 29 - Jul 30
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cozy Quechee Corner Cabin

10.0 out of 10, Exceptional, (50)
"We stayed at this darling cabin during a cross country ski race that was held at Dartmouth."
Cozy Quechee Corner Cabin

Secluded retreat in the trees

10.0 out of 10, Exceptional, (21)
"The place was great ,it fit into our budget and the owners were more than helpful."
The price is CA $199
CA $359 total
includes taxes & fees
Jul 17 - Jul 18
Secluded retreat in the trees

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (71)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (109)
"Our stay was terrific! Such a lovely renovated home! "
Beautifully renovated with fireplace and coffee bar

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (121)
"Another fun time at this well located, well appointed home."
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Off Grid Glamping Shed with River Access

2.0 star property
The price is CA $80
CA $128 total
includes taxes & fees
Jul 14 - Jul 15
Off Grid Glamping Shed with River Access

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very good, (32)
"Fun . We’ll do it again."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.6 out of 10, Exceptional, (11)
"Excellent location"
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (146)
"Loved the cabin. Great access to Sugarbush and all the MR valley has to offer. The hosts could not be nicer."
The price is CA $295
CA $601 total
includes taxes & fees
Jul 13 - Jul 14
Stetson Hollow Cabin by Stetson Brook

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (109)
"Very quiet, well appointed cottage! So peaceful, beautiful scenery and VERY accommodating host!"
Classic Vermont Cabin on 2.5 acres Lake Frontage

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is CA $247
CA $332 total
includes taxes & fees
Jul 15 - Jul 16
Mountain Green

Treehouse at Wise Pines- NoBo

9.6 out of 10, Exceptional, (9)
"We enjoyed our stay. It was a great place with great people. We had an amazing time there. "
The price is CA $225
CA $282 total
includes taxes & fees
Jul 13 - Jul 14
Treehouse at Wise Pines- NoBo

Comfortable mountain gem with pool, mountain views, & indoor parking space

8.4 out of 10, Very good, (30)
"I would recommend to friends and family "
The price is CA $86
CA $372 total
includes taxes & fees
Jul 14 - Jul 15
Comfortable mountain gem with pool, mountain views, & indoor parking space

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (55)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is CA $176
CA $277 total
includes taxes & fees
Aug 1 - Aug 2
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Spectacular dog-friendly lakefront house with washer/dryer & fast WiFi

7.8 out of 10, Good, (8)
"Beautiful place… loved the setting"
Spectacular dog-friendly lakefront house with washer/dryer & fast WiFi
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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Frequently asked questions

Are there vacation rentals in Stockbridge?

Yes, we give you a choice of vacation rentals near the most popular sights in Stockbridge, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Stockbridge has to offer?

Quaint lakefront home with a private deck, firepit, and dock: Visitors like this Stockbridge vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Stockbridge?

With 11 Expedia vacation rentals, you're sure 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 vacation rental in Stockbridge like?

A vacation rental is a private property where you can stay for several days or longer in Stockbridge. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family getaway.