Stockbridge vacation rentals

We found 1,623 vacation rentals — enter your dates for availability

Discover a selection of 10 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.

Vacation rentals with weekly discounts - Stockbridge

Showing deals for:Jul 3 - Jul 10

Image gallery for "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Exterior
9.8 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth

8% off
Price is $430
$3,009 for 7 nights
All fees included
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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Find out more about Stockbridge

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)
  • 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)
  • Saskadena Six Ski Area (13.3 mi / 21.4 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)
  • 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)
  • Lake Dunmore (18 mi / 29 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 best area to stay in Stockbridge, Vermont, United States of America when booking a vacation rental?
When planning a vacation in Stockbridge, Vermont, one of the best areas to consider for your stay is the charming neighborhood surrounding the village center. This area offers a delightful blend of local character and easy access to the natural beauty that defines Vermont. Here, you can find a variety of vacation rental options, from cozy cabins to spacious homes, making it an ideal choice for families or groups.

In addition to the beautiful scenery, this neighborhood is conveniently located near some of the region's top attractions. A short drive will take you to the stunning Green Mountain National Forest, where you can enjoy hiking, biking, and breathtaking views throughout the year. Additionally, the nearby Norman Rockwell Museum showcases the work of the renowned artist, providing a unique cultural experience that complements the picturesque surroundings.
How much does it cost to rent a vacation home in Stockbridge?
Prices for vacation rentals in Stockbridge vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Stockbridge to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Stockbridge vacation house rentals?
You can find great discounts on house rentals in Stockbridge on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Stockbridge?
In Stockbridge, vacation houses are the most popular type of rental, with about 10 available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups. Additionally, there are several chalets, cabins, and cottages that offer a rustic charm and a closer connection to nature, often including amenities such as fireplaces, outdoor spaces, and scenic views of the surrounding landscape.
Are there any family house rentals in Stockbridge?
In Stockbridge, Vermont, there are about 16 family-friendly vacation rentals available, making it a great choice for families seeking a cozy retreat. This charming area is surrounded by natural beauty, with plenty of opportunities for outdoor activities. Many of these homes feature spacious living areas ideal for family gatherings, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and explore.

Visitors can enjoy nearby attractions such as the picturesque Green Mountain National Forest and various hiking trails, which are superb for family adventures. Additionally, the town's quaint atmosphere offers local shops and eateries, contributing to a delightful experience.
Can I find long-stay vacation rentals in Stockbridge?
A long-stay vacation rental in Stockbridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Stockbridge?
In Stockbridge, Vermont, travelers will find several pet-friendly house rentals that cater to a variety of needs. Many of these homes are situated in serene, picturesque settings, offering amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces for pets to enjoy. Some properties may even include features like fenced yards or nearby walking trails, making them ideal for pet owners looking to explore the beautiful landscapes of the area.

The village is surrounded by stunning natural beauty, with access to hiking trails and opportunities for outdoor activities that are pet-friendly. Nearby attractions such as the Green Mountain National Forest provide ample space for exploration with your furry friends.
Are there any remote work vacation rentals in Stockbridge?
In Stockbridge, Vermont, there are 17 vacation rentals that cater to remote work needs. This picturesque area, known for its stunning landscapes and charming New England ambiance, provides a great backdrop for working remotely. Travelers can expect properties equipped with essential amenities such as free Wi-Fi and dedicated workspaces, allowing for productive work sessions while enjoying the tranquility of the surroundings. Many rentals also feature comfortable living areas, full kitchens for convenient meal preparation, and outdoor spaces to take breaks and soak in the fresh air. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Stockbridge vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Stockbridge with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Stockbridge?
In Stockbridge, popular vacation rental amenities cater to travelers seeking comfort and relaxation. Many rentals feature fully equipped kitchens, allowing guests to prepare their own meals, which is especially convenient for families or groups. A fireplace is a common highlight, providing warmth and a cozy atmosphere during colder months. Additionally, most properties offer outdoor decks or patios where guests can unwind and enjoy the surrounding natural beauty. Onsite parking is typically available, making it easy for visitors to explore the area. Lastly, a coffee and tea maker is often included, ensuring that guests can enjoy their favorite beverages at any time.
When is the best time to visit Stockbridge for a vacation rental?
The peak travel season in Stockbridge occurs during the vibrant summer months of June through August, with July standing out as the most popular time for visitors. This period draws many travelers seeking to immerse themselves in the natural beauty and artistic charm of the Berkshires. Warm temperatures, typically ranging from the mid-60s to the high 80s Fahrenheit, create an inclusive setting for outdoor activities such as hiking, biking, and exploring the picturesque local scenery.

During these summer months, Stockbridge becomes a hub for art enthusiasts and music lovers alike, featuring events like the renowned Tanglewood Music Festival. The lively option, combined with a variety of artisan shops and local eateries, makes it a delightful experience for those looking to enjoy both culture and nature.

For travelers seeking a more budget-friendly option, consider visiting in January. While this month is part of the low season, it offers a unique charm as well, with the opportunity to enjoy winter sports in nearby areas or cozy up in a charming rental by the fire. The tranquility of Stockbridge in January allows for a more intimate experience with the town's offerings.

Ultimately, your ideal time to visit Stockbridge will depend on whether you prefer the lively summer scene filled with activities and events or the peaceful winter ambiance superb for a relaxing retreat.
How early should I book a Stockbridge vacation rental?
Book your Stockbridge vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Stockbridge, Vermont, United States of America?
In Stockbridge, Vermont, visitors can enjoy a picturesque small-town atmosphere with a rich cultural heritage. The Norman Rockwell Museum, located nearby in Stockbridge, showcases the works of the famed American illustrator and is a must-see for art enthusiasts. The charming downtown area offers quaint shops and cafes that reflect the local character.

For nature lovers, the surrounding Berkshire Mountains provide numerous outdoor activities, including hiking and scenic drives, particularly along the scenic Route 7. The nearby Stockbridge Bowl is superb for swimming, kayaking, and picnicking during the warmer months, while the winter months bring opportunities for skiing at nearby resorts.

Additionally, the historic Naumkeag estate, a former Gilded Age home, features beautiful gardens and stunning architecture, making it a great spot for leisurely exploration.
Can I change or cancel my Stockbridge home rental booking on Vrbo?
To find Stockbridge vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Stockbridge vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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