Stockbridge Vacation Rentals from $143: Search Short-Term Rentals

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Our top choices for Stockbridge vacation rentals

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

$518 nightly

Jul 29 - Jul 30

Total with taxes and fees

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

$537 nightly

Jul 20 - Jul 21

Total with taxes and fees

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

$537 nightly

Jul 20 - Jul 21

Total with taxes and fees

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

Chelsea

Susan K.

$128 nightly

Jul 17 - Jul 18

Total with taxes and fees

Secluded retreat in the trees

Roxbury

Emily R.

$223 nightly

Jul 30 - Jul 31

Total with taxes and fees

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

Addams S.

$404 nightly

Jul 20 - Jul 21

Total with taxes and fees

Beautiful home located in the Mad River Valley

Warren

Allie T.

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Mendon

Aurore H.

$205 nightly

Jul 20 - Jul 21

Total with taxes and fees

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Top Stockbridge Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"Good location. Small pool and no chairs around pool"

Mountain Meadows Lodge

10/10 Excellent

"Everything about Mountain Meadows Lodge is AMAZING!! The husband and wife managers are the nicest people. Upon check-in Mike gave us a tour of the lodge which includes daily home baked cookies, fresh coffee, pastries, fruit, etc. Homemade breakfast every morning. Smores station to use by the firepit on the back porch which overlooks the beautiful pond. There are games, puzzles, an outdoor hot tub, sauna, pool table - so much to do! The Appalachian trail runs thru the property which leads to a beautiful waterfall. There's a small bar if you feel like having a drink after a long day of hiking or skiing. Honestly, it just felt like home, but even more relaxing! I would highly recommend Mountain Meadows Lodge."

Brandon Inn

8/10 Good

"The Brandon Inn is an attractive historic property in a small town. It is walking a line between meeting a price and offering an experience, so it might not deliver on every traveler’s hopes for a charming Vermont inn experience. If your budget allows, there are cushier options. The vibe here is very mellow, though. Management intend for you to be able to access your room with a code you would have received by text. This sort of arrangement does not work well when booking with Expedia, so expect to meet or talk to staff. The hotel is lightly staffed, but we never had a problem finding them and they were pleasant. If mobility is a concern, the historic elevator is staff-operated on request. The pool is an unexpected amenity here. I used it and very much enjoyed it. The breakfast was well provisioned, but it was unusual to see the entirety of it laid out the night before. If I were managing this place, I would employ a person to arrive in the morning to lay out the breakfast. It seems more appealing and a better food handling practice. Additionally, it was unwelcome to find a staff member operating a noisy shop-vac type device to remove crumbs from the area around the toaster oven during normal breakfast hours. Overall, this was a pleasant place to stay."

My Place Hotel-Randolph VT

8/10 Good

"1st - no dishes, silverware or cookware is included with your kitchenette. The property does have some they'll sell you. Housekeeping is only every 4th day, including trash removal. That being said, the room layout was excellent, none of that wasted space that drives you crazy when you can't turn around in the bathroom. The air conditioning was on when we got there (90+ temps that day). Its a newer property but we did have issues the door latch and no maintenance person on site. It was clean and tidy but might have the slowest elevator I've ever been in. Luckily there are only 3 floors. Overall, not a bad stay."

On The River Inn

10/10 Excellent

"Great hotel! Our room was spacious and we loved having a full size fridge and mini-kitchen. Insanely loved the bath products (sorry, I love that kind of thing!). We had a great dinner at the restaurant which has a wonderful vibe and friendly staff. When we checked in, the front desk staff forgot to mention breakfast was included (clearly I had forgotten, too)-- took me 2 days to realize that! Breakfast was great. Another plus-- the gigantic backyard/meadow adjacent to the river is stunning and smores at night were an added bonus! They do a great job creating a hotel that is perfect for families, mountain bike travelers, horse show folks, couples getaways. Hard for one place to cover all that. I had booked via an online site which I thought included all fees but there was a small daily added cost. Overall though our total expenditure was LESS than other area hotels and really, this was so beautiful, immaculate, delish and otherwise very hospitable! We will be back!"

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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 11 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.

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Check prices for these dates

Our top choices for Stockbridge vacation rentals

Gnome Home Mountain Ski Chalet w/Sauna Killington

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock

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

Secluded retreat in the trees

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Beautiful home located in the Mad River Valley

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Mountain Green

Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Stetson Hollow Cabin by Stetson Brook

Resort condo with mountain views, full kitchen, and free WiFi

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

large ski ranch hot tub close to killington pets ok

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Top-floor condo with mountain views & covered parking space

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

The Mountain Inn at Killington

Comfort Inn Rutland - Killington

Mountain Meadows Lodge

Brandon Inn

Mountain Sports Inn

The Jackson

My Place Hotel-Randolph VT

Holiday Inn Express Hotel & Suites White River Junction by IHG

On The River Inn

Find out more about Stockbridge

Frequently asked questions

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