Holiday Rentals in Stockbridge

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Holiday Rentals in Stockbridge

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views

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

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

8.4 out of 10, Very good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (94)
"My family and I loved staying at this cozy condo in Quechee. It really had everything we needed and more. The location is perfect for exploring downtown and traveling to nearby towns. We loved having the fireplace and used it every night! Vermont received a lot of snow while we were visiting, and the owners really took care of us. The whole complex was plowed nicely, and overall we were really impressed by their thoughtfullness and attention. Would definitely stay here again!"
Beautifully renovated with fireplace and coffee bar

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

9.0 out of 10, Wonderful, (45)
"Great simple, easy to get to. Close to the mountain! Everything was clean and well set up. As other reviewers have noted, its not recently updated (although furniture is all newer and very nice/comfortable) but not needed. Great for a couple or small family for an easy convenient stay near the mountain. I would highly recommend it and would likely come again!"
The price is €190
includes taxes & fees
16 Mar - 17 Mar
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

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

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

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

8.4 out of 10, Very good, (15)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is €361
includes taxes & fees
23 Feb - 24 Feb
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (142)
"Loved everything about this cabin between the stars at night to the wood burning fireplace it was perfect for us. And the hosts Jill and John were beyond accommodating and really easy on point with anything I might have needed. Proximity to Sugarbush and Mad river Glen rounded it all out to be Perfect."
The price is €464
includes taxes & fees
2 Mar - 3 Mar
Stetson Hollow Cabin by Stetson Brook

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 €184
includes taxes & fees
10 Mar - 11 Mar
Treehouse at Wise Pines- SoBo

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (50)
"This was my first experience with Vrbo. It was wonderful. Checking in and out of the property was simple! My fiancé and I were seeking a Christmas getaway in Vermont. We certainly found it! The property is in close distance to Brandon and Middlebury. Both towns have lots of dining options and shopping. We visited a brewery and winery. Our cottage in Leicester was pristine. Our host, David. was accommodating and friendly. The cottage is well built and you can see how much work David has put into...
The price is €192
includes taxes & fees
5 Mar - 6 Mar
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

9.4 out of 10, Exceptional, (36)
"Great for our family ski trip. Definitely worth the price for convenience. Great that it’s pet friendly. The space does need some updating and the beds were a little uncomfortable and the master bedroom was super dry- even with a humidifier was notable. "
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

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

9.8 out of 10, Exceptional, (10)
"Me and my wife loved this place. Perfect for a cozy getaway. "
The price is €368
includes taxes & fees
18 Mar - 19 Mar
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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, (2)
"The hosts were super communicative and accommodating to everything we needed, even going so far as to give us a tour of the property when we arrived late at night. The space is super cozy (we stayed during a snow showers and very cold weather) and we loved being able to relax in the super modern and clean living space while being able to feed all the wonderful goats just outside. Being introduced to each goat on a first name basis and being told about their personality was so funny,. We will...
The price is €154
includes taxes & fees
21 Feb - 22 Feb
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

10.0 out of 10, Exceptional, (85)
"Very nice cabin with plenty of space and supplies such as blankets, towels, kitchen gear. Everything was very easy. I’d stay again "
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

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

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

4 Season Secluded Lakefront Home near Ski Mountains

9.4 out of 10, Exceptional, (71)
"Property was clean, owners and property manager were very communicative. Property was clean, shoveled and plowed, and they were very accommodating with us arriving late. "
4 Season Secluded Lakefront Home near Ski Mountains
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, (1007)
"Paint and wall paper coming off the ceilings kinda older but was clean otherwise "
The price is €141
includes taxes & fees
3 Mar - 4 Mar
Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1000)
"You definitely stay here again. Nice hot tub and pool"
The price is €213
includes taxes & fees
17 Mar - 18 Mar
Killington Mountain Lodge, Tapestry Collection by Hilton

Align Inn Vermont

2.5 star property
9.0 out of 10, Wonderful, (1007)
"Fantastic Property! Have stayed in the past, will continue to stay in the future! "
The price is €115
includes taxes & fees
11 Mar - 12 Mar
Align Inn Vermont
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. Killington Resort 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.