Stockbridge Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Stockbridge

"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...

"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...

"very clean and easy to access close to mountain"

"My fiancé and I stayed here over Christmas break for 4 nights. Snowboarded on Killington for 3 of those days. We were in close proximity to not only the mountain, but the shops to get our boards waxed and restaurants/bars. Those restaurants/bars were essential as this rental unit only has a microwave and mini fridge (as advertised). But for a place to just kick back and relax, clean up, and sleep. It was in a prime location. The spa services were available to us and while we didn't get to use...

"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."

"We had a great winter weekend! The accommodations were just what we needed, perfect location and the coffee bar was amazing! We cant wait to come back again!"

"Apartment was exactly as described. Great place to relax when not skiing. Property manager was prompt in responding to questions."

"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."

"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."

"This was very spacious. I think you could have a nice sized group here comfortably. 4-6. The area around the property is a bit run down. Thr property owner did not send instructions to enter prior to arrival, but responded quickly and we were inside within 10 min. The wifi password would not work, so we used cell and downloaded movies nearby to watch on Kindle. The main bedroom was large with a couch or maybe a futon. There was a stove, full fridge, washer and dryer, microwave. I did not see a...

CA $360 total

includes taxes & fees

Feb 2 - Feb 3

"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. "

CA $267 total

includes taxes & fees

Feb 4 - Feb 5

"My wife and I spent three nights In this awesome cabin. There is nothing that Jeff and his family have not thought of. The cabin is incredibly cozy and accommodating. It was extremely cold during our stay but we stayed plenty warm by the fire in the cozy cabin!! Thanks Jeff for your hospitality. Your property is wonderful "

"This property is VERY well maintained! Its spacious, clean, modern, and includes a full kitchen. The electric fireplace in tbe living room area is a truly modern & romantic touch! The bed was quite firm & comfortable. The kitchen is way more stocked with cookware (basics like plates, cups, bowls, as well as pot, pan, measuring cups, cutting knives, BBQ utinsils, wine glasses, cutting board etc. etc.)than expected! Even included quite a few seasonings & cooking/olive oil! The heat worked VERY...

CA $506 total

includes taxes & fees

Feb 4 - Feb 5

"Very nice property. Clean and well appointed."

CA $543 total

includes taxes & fees

Feb 12 - Feb 13

"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...

CA $227 total

includes taxes & fees

Feb 2 - Feb 3

"Loved the room and resort. Everyone is very friendly and the room was perfect for 2-4 people. Has everything you need for a ski trip! "

"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...

"Enjoyed our stay. 5 minute drive to Jackson gore base made it nice to go back and forth with kids. Ursula was very attentive and did her best to make sure everything was in good order. "

"The property was exactly as advertised and clean. The pool was open and it was a good option to relax. The acces to parking was terrible - muddy, sandy, icy gravel. It is clear that nobody was thinking about this at all. The access to lifts was not ski in/out, but shuttle was great, and running all time! There was a ski locker, which was convenient, though nobody told us about it and we figured it out ourselves. Card for pool did not work but the office was open and provided the correct one,...

CA $604 total

includes taxes & fees

Feb 4 - Feb 5

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Other types of properties in Stockbridge you may be interested in

"Nice quiet clean hotel"

CA $199 total

includes taxes & fees

Feb 3 - Feb 4

"Great stay!"

CA $426 total

includes taxes & fees

Feb 24 - Feb 25

Combined shower/tub, eco-friendly toiletries, hair dryer, towels

"An excellent hotel well located in white river junction"

CA $181 total

includes taxes & fees

Mar 3 - Mar 4

Find out more about Stockbridge

Everything you need to know about Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stockbridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Stockbridge Vacation Rental Travel Info

Popular accommodation	Stockbridge private vacation homes
Known landmarks	Lakota Lake, Little Pico Mountain and White River Golf Club
International airports	Lebanon, NH (LEB-Lebanon Municipal) and Springfield, VT (VSF-Hartness State)

Recent reviews of Stockbridge properties

Killington Mountain Lodge, Tapestry Collection by Hilton

5/5 Excellent

"Great stay!"

A verified traveller stayed at Killington Mountain Lodge, Tapestry Collection by Hilton

Posted 2 days ago

5/5 Excellent

"This Inn is very close to Killington Ski Resort. Made it very easy to get there early. We got there very late after check in had closed but were welcomed with a note. The inn smelled wonderful when we walked through the door and was very special and inviting. We only stayed two nights, but I would have been happy here for a week. The staff was amazing and friendly and made us feel right at home. I felt more welcome to this hotel than maybe any hotel I ever stayed at. That’s a fantastic compliment. I felt like I was an old family friend. There are stairs we had to navigate to get to breakfast and out upstairs room, but didn’t bother us as our room was close to multiple doors. The seating areas throughout the inn were sweet and quaint in a fantastic way. You could sit by the fire and play games in the cute breakfast area any time of the day. Don’t buy your Killington ski tickets ahead of time as you can get them there at a discount. I wish I had known that. My teenage boys were quite happy here to. I have one suggestion and that is to make the shower a bit more user-friendly. It took me a long time to get the temperature between burning hot and too cool to shower in. It could be a problem for families with young children. But since everything was so well run, I didn’t mind and I would absolutely look forward to staying here again! "

A verified traveller stayed at Greenbrier Inn

Posted 2 days ago

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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?

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 10 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 Sugarbush Farm, or get outside and enjoy nature at Green Mountain National Forest. Appalachian Trail Adventures and Pico Mountain at Killington Ski Resort 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.

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Stockbridge Vacation Rentals

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Vacation Rentals in Stockbridge

Cozy Loft for two with Hot Tub

Cozy Loft for two with Hot Tub

Spectacular opportunity to enjoy the finest property in Killington Summit

Spectacular opportunity to enjoy the finest property in Killington Summit

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

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

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

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

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

Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

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

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

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

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

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

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

MODERN SPACIOUS 2-bedroom apartment

MODERN SPACIOUS 2-bedroom apartment

The Forest Fun Suite at Killington Center: 2RM/2BA Condo. Pool. Bus. Discounted Ski Rentals!

The Forest Fun Suite at Killington Center: 2RM/2BA Condo. Pool. Bus. Discounted Ski Rentals!

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

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

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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

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

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

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

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

Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

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

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

Other types of properties in Stockbridge you may be interested in

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

Align Inn Vermont

Align Inn Vermont

Find out more about Stockbridge

Find out more about Stockbridge

Stockbridge Vacation Rental Travel Info

Recent reviews of Stockbridge properties

Recent reviews of Stockbridge properties

Killington Mountain Lodge, Tapestry Collection by Hilton

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.ca

Frequently asked questions