Stockbridge holiday rentals

We found 1,573 holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in Stockbridge that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Stockbridge getaway

Learn about the unique charm of Stockbridge with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Stockbridge

Do you want to discover things to do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Stockbridge a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Green Mountain National Golf Course (7.2 mi / 11.5 km)
  • Appalachian Trail Adventures (7.2 mi / 11.6 km)
  • Pico Mountain at Killington Ski Resort (10.2 mi / 16.5 km)
  • Killington Golf Course (11 mi / 17.6 km)
  • Killington Resort (11 mi / 17.8 km)
  • Killington Adventure Center (11.1 mi / 17.9 km)

Exploring the natural landscape of Stockbridge

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Stockbridge is a great place to get outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Silver Lake State Park (7.9 mi / 12.7 km)
  • Lakota Lake (8.6 mi / 13.9 km)
  • Pico Peak (10.8 mi / 17.4 km)
  • Killington Peak (12.8 mi / 20.6 km)
  • Marsh-Billings-Rockefeller National Historical Park (14.9 mi / 24 km)
  • Moss Glen Falls (16.9 mi / 27.2 km)

Travelling to and around Stockbridge

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 20.1 mi (32.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Lebanon, NH (LEB-Lebanon Municipal), which is 24.8 mi (39.9 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Stockbridge?
Houses are the most popular type of holiday home in Stockbridge, according to our data. Even if you have something bigger or smaller in mind, Stayz has properties in many shapes and sizes. Explore our options to find your perfect match.
How much does it cost to rent a holiday home in Stockbridge?
Season, property type and length of stay are some of the things that can influence the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy country cottages to sprawling luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Stockbridge?
Prices for beach houses in Stockbridge may vary depending on the type and size of the property and when you’re travelling. Simply enter your dates of travel into Stayz and the number of guests to see your home options and prices. From there you can use our filter tool to tailor your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Stockbridge?
There are, yes. Choose from 12 stays that allow pets in Stockbridge on Stayz. Our furry best friends also deserve a little time out, so simply use our search function for pet-friendly holiday homes to book a property where Rover can lap up the good times.
What are popular home amenities in Stockbridge?
When it comes to home amenities that guests are looking for in Stockbridge, a fireplace, nearby museums and a firepit rank highest. With Stayz holiday homes, you’ll enjoy choices to suit your taste and style, whether you’re planning to get away with family, friends or even pets.
Are there large group holiday homes in Stockbridge?
With seven holiday homes that can host 10 people or more in Stockbridge, you won’t have to hold back on your invites. From holidays with the extended family to special events like Christmas and birthday parties, Stayz will help you find a large group home to suit the occasion.
Are there holiday homes in Stockbridge that welcome kids?
Bring the whole family together for a fun-packed adventure in Stockbridge at one of our 12 family-friendly holiday homes. Lots of these stays come with amenities that are just perfect for getaways with the kids, like laundries, living rooms and entertainment units. Simply check the “Properties good for families” filter box and pick out your favourite.
What are the top attractions for families in Stockbridge?
Keeping the kids happy during your Stockbridge holiday is child’s play with these cool family-friendly attractions:

  • Little Pico Mountain
  • Lakota Lake
  • White River Golf Club

Are there one-bedroom holiday homes in Stockbridge?
Yes, you can pick from two one-bedroom homes in Stockbridge. Whether you’re on the lookout for a secluded cottage or a condo, our one-bedroom properties are ideal if you don’t need tons of space. One of the best parts about having your own digs? You’ll never have to share your holiday with strangers.
Are there holiday homes with WiFi in Stockbridge?
You’ll find four holiday homes with WiFi in Stockbridge. If you’d like to disconnect from the world on your break, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Stockbridge?
Choose from two holiday homes with air conditioning in Stockbridge providing that cool, cool breeze and extra level of comfort. Simply enter your chosen travel dates and then take advantage of our filters to search for stays with air conditioning.
How old do you have to be to rent a holiday home in Stockbridge?
The age limit can differ between properties on Stayz, so be sure to look at the rules of the holiday home in Stockbridge you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a holiday home in Stockbridge for?
The amount of time you can stay in a Stockbridge holiday home for is up to the property. Simply put in your preferred travel dates to browse available options that offer long-term stays. They come with all you need to make your extended trip more convenient and comfortable, such as air conditioning and kitchens. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stay even longer for less.

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