Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Mountain Green

2.0 star property
5.8 out of 10, (8)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is AU$477
includes taxes & fees
20 Mar - 21 Mar
Mountain Green

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (232)
"Jeff was extremely responsive. Great little place."
Cozy Loft for two with Hot Tub & Mtn Views

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

10.0 out of 10, Exceptional, (483)
"We had a great time at the cabin, our second year!! We plan to be back for a third season!!Everything was perfect, the coziness of the cabin was amazing. We were able to watch the Super Bowl again on the huge projection screen!! Hot tub was great after several long days of skiing and snowshoeing!!"
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (98)
"Excellent house, very clean, has everything you need. The checkin process was very smooth, and the hosts were quick to respond when something wasn't working (only because I had accidentally unplugged it!). They did a great job clearing the snow from the house after the storm and the location/parking/access to Quechee was great! Thank you!"
Beautifully renovated with fireplace and coffee bar

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

8.6 out of 10, Excellent, (28)
" 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

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 AU$582
includes taxes & fees
16 Mar - 17 Mar
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (47)
"Great location, clean room and just enough space! Price point fair. Will stay again for sure!!"
The price is AU$310
includes taxes & fees
16 Mar - 17 Mar
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (20)
"The gondola house was perfect for our group. It was spacious and comfortable. Loved having a bathroom on every floor. It was well stocked with everything we could’ve needed. I don’t have one bad thing to say about it. The hot tub was just lovely after a long day of skiing. Would not hesitate to rent this again and highly recommend it."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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 AU$292
includes taxes & fees
1 Apr - 2 Apr
Treehouse at Wise Pines- SoBo

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

9.2 out of 10, Wonderful, (7)
"Condo was perfect for our weekend ski getaway the bus to the K! lodge runs about every 15 min. to the front door of the building will defiantly stay again"
The price is AU$498
includes taxes & fees
16 Mar - 17 Mar
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

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 AU$314
includes taxes & fees
13 Mar - 14 Mar
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Cozy Quechee Corner Cabin

10.0 out of 10, Exceptional, (48)
"We stayed at this darling cabin during a cross country ski race that was held at Dartmouth."
Cozy Quechee Corner Cabin

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

10.0 out of 10, Exceptional, (21)
"This was our third time skiing at Okemo and was without doubt the best. Access to the slopes is so easy and the unit itself is top notch. Loved everything about it! "
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

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

10.0 out of 10, Exceptional, (11)
"My family and I stayed at the cabin over school vacation and skied at Okemo. The cabin is great. Well designed, new, clean. Very comfortable for my family of 4. We hit the hot tub apres ski which was a nice treat. Would book again. "
The price is AU$547
includes taxes & fees
8 Apr - 9 Apr
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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, (6)
"Everything was excellent. 3 baths 3 beds. Perfect. Bring coffee filters and hangers."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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, (4)
"This property is so cool and unique! After a long day on the trails it was great to come to the barn say hi to the goats and step in to the bungalow and it was nice and warm. The owner was so cooperative with the check in process as he met me first thing in the morning so I could go enjoy the trails. Trails lead right to the door! Thank you for a great stay and will return very soon"
The price is AU$252
includes taxes & fees
13 Mar - 14 Mar
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (22)
"This place was great, Communication with the Killington Rental Associates was wonderful. The house was as it photographs. It was a perfect spot to ring in the New Year. After skiing, the hot tub and Sauna were a welcome retreat for the weary skiing crowd, the Kitchen was well stocked with just about anything you could need to prepare meals for a large crowd. The Bar was an added highlight for apre-Ski. There was enough space for a large crowd to gather in one spot, and enough spots to...
Spectacular opportunity to enjoy the finest property in Killington Summit

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (169)
"3 moms and 3 teens had a fantastic weekend! The condo was great. The boys loved being able to walk out the door to the trails. 2 full days of boarding. The condo met all of our needs perfectly! "
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

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

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
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

Align Inn Vermont

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Very clean and nice"
The price is AU$192
includes taxes & fees
30 Mar - 31 Mar
Align Inn Vermont

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1006)
"Very nice! "
The price is AU$218
includes taxes & fees
16 Mar - 17 Mar
Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1000)
"My daughter and I had a great stay for the weekend!"
The price is AU$261
includes taxes & fees
2 Apr - 3 Apr
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 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.