Stockbridge Vacation Rentals

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Vacation Rentals in Stockbridge

Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (58)
"Was just visiting Vermont to fish for the weekend so I didn’t need anything fancy but it was quite nice"
Beautifully renovated with fireplace and coffee bar
1 bedroom
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is CA $205
CA $253 total
includes taxes & fees
May 27 - May 28
Treehouse at Wise Pines- SoBo
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is CA $321
CA $705 total
includes taxes & fees
Jun 1 - Jun 2
Idyllic Lakefront House Suited Two Families
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
The price is CA $136
CA $467 total
includes taxes & fees
May 26 - May 27
Killington Center Inn & Suites by Killington VR - Studios
Fridge, microwave, oven, stovetop
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Fridge, microwave, oven, stovetop
Luxurious Secluded Cottage Massage Studio on Site
10.0 out of 10, Exceptional, (34)
"Beautiful cottage equipped with everything you might need. Incredibly clean, comfortable and a helpful, friendly host."
The price is CA $226
CA $331 total
includes taxes & fees
May 27 - May 28
Luxurious Secluded Cottage Massage Studio on Site
Interior
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
8.0 out of 10, Very good, (14)
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
TV, fireplace, DVD player
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
9.6 out of 10, Exceptional, (46)
"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Classic Vermont Cabin on 2.5 acres Lake Frontage
9.8 out of 10, Exceptional, (91)
"We can not say enough wonderful things about our stay. Brian was there to meet us and do a walk though of the property and even helped us out with local places to go. He is a gem! Although it rained it was absolutely perfect. The yard gave our pups a place to run free but there was also cute areas to walk them all around the area. The views of the water are incredible. Just sad it was too cold to jump in... maybe next time. October was the perfect time to see all the leaves changing and breathe...
Classic Vermont Cabin on 2.5 acres Lake Frontage
Property grounds
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
9.2 out of 10, Wonderful, (13)
"Great little cabin - really enjoyed our stay"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Exterior
Cozy Studio for 4 - Walk to Mountain w/ Balcony
9.0 out of 10, Wonderful, (12)
"Great location. Hot tub, salt water pool, steam room and sauna were welcomed after a day on Superstar! Beautiful locker rooms and facilities. Easy drop off of “schlep” at the parking garage to the room. Bus carts available too. We would definitely stay again."
The price is CA $115
CA $266 total
includes taxes & fees
May 27 - May 28
Cozy Studio for 4 - Walk to Mountain w/ Balcony
Indoor pool, outdoor pool
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Don't see what you're looking for?
See all available properties in Stockbridge
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.

Stockbridge Vacation Rental Travel Info

Other types of properties in Stockbridge you may be interested in

Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, (1000)
"This was a wonderful stay. Everyone, from front desk check in, to bartender, to Starbucks barista were warm, inviting, friendly, and helpful. The room was spotless. Appointed as advertised, and well cared for each day. I was pleasantly surprised and impressed overall. "
The price is CA $179
CA $197 total
includes taxes & fees
Jun 5 - Jun 6
Killington Mountain Lodge, Tapestry Collection by Hilton
Indoor pool
Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, (1004)
"No USB"
The price is CA $194
CA $213 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Inn Trolley Square
Lobby
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (441)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."
The price is CA $465
CA $512 total
includes taxes & fees
May 28 - May 29
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stockbridge. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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

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.

Recent reviews of Stockbridge properties
Expedia verified reviews