Stockbridge holiday lettings

We found 1,622 holiday rentals — enter your dates for availability

Discover a selection of 12 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.

Holiday rentals with weekly discounts - Stockbridge

Showing deals for:10 Jul - 17 Jul

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

7% off
Price is £2,539
for 7 nights, 1 chalet
£363 per night
includes taxes & fees
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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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)
  • 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 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)
  • 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)

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 best area to stay in Stockbridge when booking a holiday rental?
When considering a holiday rental in Stockbridge, Vermont, a popular area to stay is the picturesque village itself, known for its charming New England atmosphere. Stockbridge features a modest selection of properties, allowing visitors to immerse themselves in the local culture and enjoy a quaint, community-oriented experience.

The village is surrounded by beautiful landscapes, making it ideal for outdoor enthusiasts. Nearby, you'll find the stunning Green Mountain National Forest, which offers a range of activities such as hiking and birdwatching, showcasing Vermont's natural beauty. Additionally, the Norman Rockwell Museum, located just a short drive away, celebrates the famed illustrator's work and offers a glimpse into American art and culture.
How much does it cost to rent a holiday home in Stockbridge?
Prices for holiday 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 holiday 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.
Where are the best Stockbridge ski resort rentals?
For the best ski resort rentals near Stockbridge, Vermont, travellers should consider the nearby area of Lenox and the charming village of Great Barrington. These locations provide convenient access to the picturesque slopes of the Berkshires, particularly at ski areas like Jiminy Peak, which is within a short drive. In Lenox, you can find a variety of rental properties, including cosy cabins and spacious chalets, many featuring amenities such as fireplaces, hot tubs, and fully equipped kitchens to cater to families or groups looking for a comfortable stay after a day on the slopes.

Great Barrington also offers a selection of rentals, ranging from modern condos to rustic lodges. Many of these properties come with essential amenities like Wi-Fi, laundry facilities, and convenient parking, making them ideal for skiers. The area is rich in local charm, with numerous shops, cafés, and restaurants that provide a lively après-ski scene.

Additionally, the stunning natural beauty of the Berkshires allows for year-round outdoor activities beyond skiing, such as hiking and exploring nearby parks.
What is the most popular type of holiday rental accomodation in Stockbridge?
In Stockbridge, holiday houses are the most popular type of holiday rental, with about 30 available in the area. These properties usually feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the picturesque surroundings. Chalet rentals also attract visitors, with around 12 options that often provide a rustic charm combined with modern amenities, making them suitable for a cosy getaway. Additionally, there are several cabins and cottages scattered throughout Stockbridge, offering a more intimate and serene atmosphere, often set amidst nature.
Are there any family house rentals in Stockbridge?
In Stockbridge, Vermont, there are several family-friendly house rentals available, with around 16 options to choose from. This charming area is known for its picturesque landscapes and outdoor activities, making it an excellent choice for families. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or relax.

Visitors can expect amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or fireplaces to enhance their stay. The locale is also conveniently located near attractions like the scenic Green Mountain National Forest, which offers opportunities for hiking and exploring nature. Additionally, nearby towns like Great Barrington and Lenox provide cultural experiences, including museums and local dining options, ensuring there's something for everyone.
Can I find long-stay holiday rentals in Stockbridge?
A long-stay holiday rental in Stockbridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Stockbridge?
In Stockbridge, several pet-friendly house rentals are available, providing an inviting space for those travelling with furry companions. Many of these homes come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can play. The serene surroundings of Stockbridge offer a picturesque setting, ideal for relaxation and outdoor activities.

Nearby, the stunning landscapes of the Green Mountain National Forest present excellent opportunities for hiking and exploring with your pets. This area is known for its scenic trails and beautiful vistas, allowing for enjoyable adventures in nature.
Are there any remote work holiday rentals in Stockbridge?
In Stockbridge, Vermont, there are numerous holiday rentals suitable for remote work, with around 51 options available. This picturesque town offers a tranquil environment superb for productivity, surrounded by the stunning landscapes of the Green Mountains. Many of these properties come equipped with reliable high-speed Wi-Fi, ensuring that you can stay connected while enjoying your work.

Travellers can expect a variety of amenities, including comfortable workspaces, fully equipped kitchens for meal preparation, and cosy living areas to unwind after a day of work. Some rentals may even feature additional perks such as scenic views, outdoor spaces for relaxation, and proximity to local attractions like the nearby Appalachian Trail, which provides excellent opportunities for hiking during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Stockbridge holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Stockbridge with parking available—perfect for families or travellers 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 rental amenities typically include kitchens, which allow guests to prepare their own meals, and fireplaces, providing a warm, cosy atmosphere, especially during the colder months. Many properties also feature decks or patios, ideal for relaxing outdoors and taking in the scenic views of the surrounding landscape. Onsite parking is commonly available, making it convenient for travellers with vehicles. Additionally, a coffee or tea maker is often included, ensuring that guests can enjoy a hot beverage at their leisure.
When is the best time to visit Stockbridge for a holiday rental?
The best time to visit Stockbridge for a holiday rental is during the peak season from June to August. This vibrant period attracts visitors eager to embrace the stunning landscapes and outdoor activities that the area has to offer. With warm temperatures typically ranging from 20 to 30 degrees Celsius, it's great for exploring the charming town, hiking nearby trails, or enjoying a leisurely picnic by the riverside.

July stands out as the most popular month, bringing a bustling atmosphere filled with family-friendly events, art festivals, and concerts. The lush greenery and blooming flowers create a picturesque setting, ideal for those who love nature and seek to immerse themselves in local culture.

For those looking for a more budget-friendly option, consider visiting in January. While it is the low season, this month offers a unique charm, with the possibility of winter activities like snowshoeing and cross-country skiing, all against a stunning snowy backdrop.

Ultimately, the best time to visit Stockbridge depends on whether you prefer the lively summer scene filled with activities or the tranquil beauty of winter's embrace.
How early should I book a Stockbridge holiday rental?
Book your Stockbridge holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Stockbridge?
In Stockbridge, Vermont, visitors can enjoy a variety of attractions that showcase the beauty and charm of the area. One of the highlights is the Norman Rockwell Museum, which celebrates the works of the iconic American artist and is situated along the banks of the Housatonic River. This museum is a major draw for art lovers and those interested in American culture.

The picturesque village itself offers lovely walking paths and quaint shops, making it a delightful spot to explore. Nearby, the Stockbridge Bowl is superb for swimming, kayaking, and picnicking during the warmer months, while in winter, the surrounding area provides opportunities for skiing and snowshoeing.

For outdoor enthusiasts, the nearby Lenox and the Berkshire Mountains offer stunning hiking trails and scenic views, while Tanglewood, the summer home of the Boston Symphony Orchestra, is just a short drive away, attracting music lovers to its performances in a beautiful outdoor setting.
Can I change or cancel my Stockbridge home rental booking on Vrbo?
To find Stockbridge holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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