Stockbridge vacation rentals

We found 1,567 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Stockbridge that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.
  • 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, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Stockbridge

Find out more about Stockbridge

Why visit Stockbridge

  1. Outdoor adventures: Stockbridge offers thrilling skiing and a variety of outdoor activities, perfect for adventure seekers.
  2. Picturesque landscapes: Enjoy the stunning natural beauty and romantic scenery of the surrounding Columbia County.
  3. Cultural attractions: Explore local museums, libraries, and historical sites, ideal for families and culture enthusiasts.
  4. Diverse accommodation options: Choose from a range of vacation rentals, including cozy cabins and charming homes.
  5. Friendly atmosphere: Experience the warm hospitality and local charm that make Stockbridge a welcoming destination.

Popular types of accommodation in Stockbridge

Discover the charm of Stockbridge with our diverse selection of vacation rentals, including private homes, condos, and cozy cabins. Whether you're seeking a short-term rental for a family getaway or an apartment finder for a romantic escape, we have the ideal rental to suit your needs. Enjoy transparency and savings while exploring this beautiful destination, and make your stay in Stockbridge truly memorable.

  • Houses: The top choice for visitors to Stockbridge, offering spacious accommodations perfect for families, friends, or couples seeking a home-like experience.
  • Condos: A popular option that combines comfort and convenience, ideal for those looking for a modern stay with amenities.
  • Cabins: These charming retreats provide a rustic atmosphere, perfect for nature enthusiasts looking to escape the hustle and bustle.
  • Apartments: Cozy and convenient, apartments are a great choice for those wanting a home base to explore the area.
  • Cottages: A delightful option for an intimate getaway, offering a warm and inviting atmosphere.**

Top attractions in Stockbridge

Stockbridge, Vermont, is an ideal destination for those seeking outdoor adventures and winter sports. Visitors can explore a variety of attractions, including national parks, museums, and libraries, perfect for families and culture enthusiasts alike. Whether you're hitting the slopes or enjoying the scenic beauty, Stockbridge offers a unique blend of activities for every traveller. Embrace the local charm and make unforgettable memories in this picturesque town.

  1. Silver Lake State Park: Just 12.9km from Stockbridge, this scenic park offers stunning views, adventure activities like hiking and kayaking, and a tranquil outdoor atmosphere perfect for nature lovers.
  2. Killington Golf Course: Located 17.7km away, this welcoming golf course features beautifully manicured greens and friendly staff, making it an ideal spot for both seasoned golfers and beginners.
  3. Fire Tower: Situated 14.5km from Stockbridge, this lookout provides breathtaking views, perfect for a romantic outing or an adventurous hike through the surrounding wilderness.

Things to do recommended for couples

For a romantic getaway in Stockbridge, consider skiing at Pico Mountain or exploring the adventure-filled Pico Peak. Don’t miss the scenic ride on the K-1 Express Gondola for breathtaking views together. Enjoy the exhilarating winter vibes and create lasting memories in this charming Vermont locale.

Things to do recommended for families

Experience family fun at the Killington School for Tennis, just 14.5km from Stockbridge, where wellness meets recreation. For some excitement, head to the Union Arena Community Center, located 25.7km away, for ice skating and adventure-filled entertainment.

Things to do recommended for groups

Enjoy a round of golf with your group at the scenic White River Golf Club, located 6.4km from Stockbridge. For shopping enthusiasts, Black Dog Sports is an 17.7km drive away. Experience culture and entertainment at the Paramount Theater, just 27.4km away, perfect for family outings.

What do I need to keep in mind when booking a vacation in Stockbridge

When planning your trip, whether you’re travelling with a group, family, pets, or seeking extended stays, it’s important to prioritise your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Stockbridge with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Stockbridge with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Stockbridge: For many, a family vacation isn't truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Stockbridge: If you're in search of vacation rentals offering discounts for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include additional preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Stockbridge

Stockbridge, Vermont, is a hidden gem for adventurers and families alike. Nestled in a picturesque setting, it offers thrilling skiing and outdoor activities. Nearby, Columbia County boasts romantic landscapes and recreation opportunities, perfect for a relaxing getaway. Experience the charm of this region, where scenic views and friendly atmospheres await every traveller, making it an ideal destination for your vacation.

  • Killington: Located 11.3km from Stockbridge, Killington is a vibrant city renowned for its impressive ski slopes and outdoor adventures. This popular destination draws travellers seeking excitement in both winter and summer months. In addition to skiing, visitors can engage in mountain biking, hiking, and scenic chairlift rides. The area's breathtaking mountains, serene lakes, and picturesque valleys provide perfect backdrops for outdoor enthusiasts. Killington Ski Resort is a standout attraction, offering a variety of winter sports and activities, ensuring an unforgettable experience for adventurers.
  • Pittsfield: Just 4.8km away from Stockbridge, Pittsfield is a charming city that shares a similar appeal with its focus on outdoor sports and recreation. Known for its inviting atmosphere, Pittsfield is another great spot for skiing and winter sports, with easy access to ski fields and resorts. The surrounding landscape features beautiful valleys, tranquil lakes, and rolling mountains, making it a picturesque setting for any outdoor activity. Whether you’re hitting the slopes or enjoying a peaceful day by the lake, Pittsfield promises a delightful getaway.
  • Gaysville: Nestled within the area of Stockbridge, Gaysville is a quaint village known for its outdoor charm and adventure opportunities. This inviting community is ideal for those looking to immerse themselves in nature, with ready access to ski fields and resorts. The local attractions focus on outdoor activities, allowing visitors to enjoy skiing and exploring the scenic valley and lake views. Whether you’re an avid skier or simply looking to unwind in a serene environment, Gaysville offers a cozy and welcoming retreat.

Best time to go to Stockbridge

If you're planning a trip to Stockbridge, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January17.8°F (-7.9°C)Light RainMostly CloudySlightly LowModerately High
February20.1°F (-6.6°C)Light RainMostly CloudySlightly LowModerately High
March28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage
April40.6°F (4.8°C)Light RainMostly CloudyAverageModerately Low
May54.1°F (12.3°C)Light RainMostly SunnyAverageModerately Low
June61.5°F (16.4°C)Light RainMostly SunnySlightly HighAverage
July67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
August65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
September58.6°F (14.8°C)Light RainMostly SunnySlightly HighModerately Low
October46.9°F (8.3°C)Light RainMostly CloudyAverageAverage
November34.5°F (1.4°C)Light RainMostly CloudySlightly LowAverage
December25.0°F (-3.9°C)Light RainMostly CloudyAverageModerately High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your trips, allowing you to start fresh, resume previous plans, or manage your itineraries efficiently. You can view your saved or booked properties, organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Stockbridge getaway

Experience the unique character of Stockbridge with a stay in a vacation home rental. There's no shortage of things to see and do in the area.If you're looking for accommodations with space to entertain friends and family, Vrbo 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 attractions to see during your stay? Venture out of your cozy vacation rental and check out everything that makes Stockbridge a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 fun outdoor activities or just want to spend some time taking in the scenery, Stockbridge is a great place to get out in nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling 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 center. If you can't find a flight that works for your travel itinerary, you could also fly into Lebanon, NH (LEB-Lebanon Municipal), which is 24.8 mi (39.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Stockbridge?
Houses are the most popular type of vacation rental in Stockbridge, according to our data. Even if you have something bigger or smaller in mind, Vrbo has properties in many shapes and sizes. Explore our options to find your perfect match.
How much does it cost to rent a vacation rental in Stockbridge?
Season, property type and length of stay are some of the things that can influence the price of a vacation home. Simply click on your dates of travel to find your dream escape. From cozy country cottages to sprawling luxury villas, all Vrbo vacation rentals 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 traveling. Simply enter your dates of travel into Vrbo and the number of guests to see your rental 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 vacation rentals in Stockbridge?
There are, yes. Choose from 12 stays that allow pets in Stockbridge on Vrbo. Our furry best friends also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to book a property where Rover can lap up the good times.
What are popular rental amenities in Stockbridge?
When it comes to rental amenities that guests are looking for in Stockbridge, a fireplace, nearby museums and a firepit rank highest. With Vrbo vacation rentals, 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 vacation rentals in Stockbridge?
With seven vacation rentals that can host 10 people or more in Stockbridge, you won’t have to hold back on your invites. From vacations with the extended family to special events like Christmas and birthday parties, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Stockbridge that welcome kids?
Bring the whole family together for a fun-packed adventure in Stockbridge at one of our 12 family-friendly vacation 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 favorite.
What are the top attractions for families in Stockbridge?
Keeping the kids happy during your Stockbridge vacation is child’s play with these cool family-friendly attractions:

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

Are there one-bedroom vacation rentals in Stockbridge?
Yes, you can pick from two one-bedroom rentals 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 vacation with strangers.
Are there vacation rentals with WiFi in Stockbridge?
You’ll find four vacation rentals 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 Vrbo.
How can I find vacation rentals with air conditioning in Stockbridge?
Choose from two vacation rentals 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 vacation rental in Stockbridge?
The age limit can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Stockbridge you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Stockbridge for?
The amount of time you can stay in a Stockbridge vacation rental 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 Vrbo vacation properties may also offer weekly or monthly discounts, so you can stay even longer for less.

People also search for

More Vacation Rentals ideas