Stockbridge Vacation Rentals

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Vacation Rentals in Stockbridge

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (489)
"Took a ride up for a nice little retreat and for my wife’s bday, such a treat! Jeff even stopped by with some wine as a gift, since I had mentioned it when booking. The space is super cozy and functional, and the hot tub was great way to relax at the end of the day. The gas fireplace gets things nice and warm, too! It had been a while since I personally visited this area of Vermont, super beautiful and remote, but still not too long of a drive to several areas of interest. Looking forward to...
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
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, (236)
"My wife and I stayed in "The Little Loft" for a ski trip to Sugarbush. The cabin it small for sure but offers everything you will need from a standpoint of short term livability. We used that hot tub daily / nightly after skiing all day, had a great meal we grilled out and had a few nice bonfires as well. If you do not want to have to drive 30 minutes for dinner or shop for your food and cook it, then you may find it a small inconvenience but for us we intentionally wanted to be in a quiet cabin...
Cozy Loft for two with Hot Tub & Mtn Views

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We had a great time-- the apartment was clean and cute and the linens fresh. "
The price is CA $276
CA $371 total
includes taxes & fees
Apr 12 - Apr 13
Mountain Green

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (100)
"We had a wonderful stay at Wanda and Eran's condo in Quechee. The home was beautiful, very clean, and looks just like the photos. The kitchen is well stocked with dishes, pots and pans and spices/cooking oils. Wanda was extremely helpful with restaurant suggestions, local activities and was very responsive."
Beautifully renovated with fireplace and coffee bar

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

8.4 out of 10, Very good, (29)
" Convenient location right off Killington Rd. Short drive to ski or restaurants. One bar/restaurant on site- Vermont Craft. Newly renovated studio, clean on arrival. Check-in as described, did not need to contact host during stay. Thorough details provided in pre arrival communications. "
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (206)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (145)
"This little cabin nails it. Charming log-cabin decor with two comfortable beds in lofts. You can look out the skylights to the trees (and the stars) while lying in bed. The kitchen has everything you need - perhaps not ideal for cooking huge meals but great for breakfast and other basic meals. The fireplace and wood stove are huge bonuses, and Jill and John keep it stocked with everything you need to build a fire. There's no television, which we saw as a huge bonus, and there is good wi-fi. It's...
The price is CA $335
CA $652 total
includes taxes & fees
Apr 13 - Apr 14
Stetson Hollow Cabin by Stetson Brook

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.6 out of 10, Excellent, (17)
"Thanks for everything "
The price is CA $161
CA $500 total
includes taxes & fees
Apr 12 - Apr 13
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

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, (5)
"We don't usually visit Vermont in mud season so that was an education in itself. But we came to see family: the goats were just an added bonus adventure, a little test to see if the city kids would enjoy the farm. 100% wonderful experience: feeding a pen full of friendly baby goats, softer than puppies, milking a momma goat, learning their names, markings, the business, etc, just a delight. Dave & Miken showed love & enthusiasm for the work, & for my children. The cabin was very warm & cozy,...
The price is CA $168
CA $219 total
includes taxes & fees
Apr 12 - Apr 13
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.2 out of 10, Wonderful, (38)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (31)
"House was exactly as described in listing."
The price is CA $161
CA $644 total
includes taxes & fees
Apr 12 - Apr 13
Spacious country home, beautiful sunsets, 40 acres

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The place is everything it describes, however I missed the part where the bathrooms are in a separate building and they are shared. Thankfully for us there was nobody else staying there. Everything was very clean. Other than that I was satisfied. "
The price is CA $202
CA $253 total
includes taxes & fees
Apr 13 - Apr 14
Treehouse at Wise Pines- SoBo

Doc's Lake house 1st floor, 2 bedroom apartment

10.0 out of 10, Exceptional, (65)
"Very clean and comfortable rental. "
Doc's Lake house 1st floor, 2 bedroom apartment

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (106)
"Beautiful area for short 4 day stay . Cabin was clean and cozy. Well stocked for pretty much anything . Only dislike was the bedroom was in a loft area with narrow steps , and a bit tough to navigate in the middle of the night when the restroom was needed . Loved the quaintness otherwise . "
Classic Vermont Cabin on 2.5 acres Lake Frontage

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

3.0 star property
9.8 out of 10, Exceptional, (7)
"The location of this unit was ideal for people who like to vacation without having to drive. We literally skied to The Sunrise Cafe for dinner the first night. All of our outdoor adventures started right from our door with excellent access to trails. The Community center had a great hot tub and free equipment to use. We would definitely go back. "
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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

8.4 out of 10, Very good, (29)
"I would recommend to friends and family "
The price is CA $74
CA $380 total
includes taxes & fees
Apr 13 - Apr 14
Comfortable mountain gem with pool, mountain views, & indoor parking space

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.2 out of 10, Wonderful, (75)
"We were a mixed group, one family of 4 and two additional adults. So we had private bedrooms for all. The house was a mix of rustic charm and some newer house elements. We were just there one night, so did not spend a whole lot of time at the house, but it was a perfect fit for our needs. Thanks Bethany!"
The price is CA $140
CA $441 total
includes taxes & fees
Apr 13 - Apr 14
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (52)
"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 $175
CA $274 total
includes taxes & fees
Apr 20 - Apr 21
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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 Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1005)
"."
The price is CA $171
CA $188 total
includes taxes & fees
Apr 13 - Apr 14
Comfort Inn Rutland - Killington

Align Inn Vermont

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Great option for Quechee!!"
The price is CA $151
CA $166 total
includes taxes & fees
Apr 27 - Apr 28
Align Inn Vermont

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (508)
"Wood fireplace in the lobby a lot of seating areas. The staff was excellent. Excellent food."
The price is CA $417
CA $521 total
includes taxes & fees
Apr 14 - Apr 15
Woodstock Inn & Resort
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 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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: Visitors like this Stockbridge vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Stockbridge?

With 13 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.