Stockbridge holiday lettings

We found 758 holiday rentals — enter your dates for availability

Discover a selection of 31 homes and other holiday rentals in Stockbridge that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Stockbridge

Showing deals for:13 Feb - 20 Feb

Image gallery for Little House in the Woods by Evergreen Home

Welcome to the Little House!
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Little House in the Woods by Evergreen Home

Sheffield, MA

11% off
Price is £2,147
for 7 nights, 1 home
£307 per night
includes taxes & fees
Little House in the Woods by Evergreen Home

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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Stockbridge

  • Historic charm: Discover the rich history of Stockbridge through its iconic historic houses and charming High Street, filled with quaint shops and delightful eateries.
  • Scenic landscapes: Enjoy the natural beauty of serene lakes and nature reserves, perfect for family-friendly outdoor activities.
  • Romantic getaways: Experience a tranquil retreat in a picturesque setting, ideal for couples seeking romance.
  • Diverse accommodation: Choose from charming holiday homes, stylish condos, and quaint cottages for a cosy stay.
  • Community atmosphere: Explore the friendly neighbourhoods that embody a welcoming and family-oriented vibe.

Popular types of accommodation in Stockbridge

Discover the perfect getaway with our selection of Stockbridge vacation rentals, featuring charming private holiday homes, stylish condos, and quaint cottages. Whether you're seeking a cosy retreat or a spacious house for the family, Stockbridge offers diverse options to suit every traveller. Enjoy the beauty of the surrounding Hamptons while experiencing transparent pricing and reassurance in your booking. Explore our holiday lettings for an unforgettable stay in this picturesque destination.

  • Houses: The top choice for visitors in Stockbridge, ideal for families or groups seeking ample space and comfort.
  • Condos: A popular second option, these offer modern amenities and often stunning views.
  • Cottages: Quaint and charming, cottages provide a cosy retreat amidst the scenic beauty of Stockbridge.
  • Apartments: Convenient and versatile, perfect for shorter stays in the heart of the area.
  • Cabins: Rustic and inviting, cabins offer a unique experience in the surrounding nature.**

Top attractions in and around Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of culture, romance, and entertainment for visitors. With attractions such as historic houses, nature reserves, and serene lakes, the area caters to those seeking family-friendly outdoor experiences. Whether you're exploring the rich history or enjoying the beautiful landscapes, Stockbridge promises a memorable getaway for all types of travellers.

  • National Shrine of the Divine Mercy: This serene shrine in Stockbridge offers a tranquil atmosphere, perfect for reflection and spiritual connection, surrounded by beautiful gardens and stunning architecture.
  • Norman Rockwell Museum: Dedicated to the iconic American artist, this museum houses an extensive collection of his works, providing insight into his life and the cultural narratives he captured through his art.
  • The Mount: Once the home of author Edith Wharton, this historic house features exquisite gardens and scenic views, allowing visitors to explore both her literary legacy and the property’s rich history.

Things to do recommended for couples

If you're seeking a romantic getaway in Stockbridge, enjoy a concert at the enchanting Tanglewood Music Center, just 3.1km away. For a thrilling day, head to Ski Butternut, 4.3km distant, or indulge in a wine tasting at Furnace Brook Winery, 5.0km away, perfect for couples.

Things to do recommended for families

Families visiting Stockbridge can unwind at Lake Mansfield Park, a delightful recreational area 3.7km away, perfect for wellness and relaxation. Alternatively, explore Tyringham Cobble, located 3.1km from Stockbridge, offering a serene environment for family bonding amidst nature.

Things to do recommended for groups

Groups visiting Stockbridge can enjoy a captivating performance at the Berkshire Theatre Festival, indulge in unique finds at the Berkshire Mountain Country Store just 2.5km away, and unwind with a round of golf at Wyndhurst Golf & Club, located 3.1km from the town.

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

Regardless of whether you’re travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s essential to filter based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Stockbridge with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Stockbridge with young kids: Travelling with young children can present its challenges. It's essential to prioritise 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 family-friendly attractions.
  • Taking your pets with you to Stockbridge: For many families, a holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Stockbridge: If you’re seeking holiday rentals with offers for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of culture and romance, perfect for a relaxing getaway. Explore the charming High Street, lined with quaint shops and eateries, or wander through the scenic neighbourhoods that embody a family-friendly atmosphere. Nearby, you'll find iconic spots like Princes Street, where modern living meets historical charm. Whether you seek a romantic escape or a tranquil retreat, Stockbridge promises an unforgettable experience amidst its picturesque surroundings.

  • Lenox: Lenox is a charming town located 3.1km from Stockbridge, renowned for its vibrant cultural scene and romantic atmosphere. It provides an array of entertainment options, from music concerts to theatre performances, making it a delightful destination for families and couples alike. Outdoor enthusiasts can also enjoy its beautiful lakes and scenic mountains. With several event and conference venues, Lenox is perfect for those looking to combine leisure with business. The town's picturesque setting and community events create a welcoming environment for all visitors.
  • The Berkshires: Situated 7.5km from Stockbridge, The Berkshires is a haven for outdoor adventurers and nature enthusiasts. Known for its stunning scenery, this region offers numerous skiing opportunities, with access to ski fields and resorts that cater to all skill levels. Whether you’re hitting the slopes in winter or exploring the lush trails in summer, The Berkshires promises an unforgettable experience. The local lakes and mountains provide a picturesque backdrop, and various event venues enhance the area’s appeal for those seeking both adventure and relaxation.
  • Great Barrington: Located 4.3km away from Stockbridge, Great Barrington is an energetic town perfect for sports and adventure lovers. The area is particularly popular for skiing, with multiple ski fields and resorts nearby, appealing to both beginners and seasoned skiers. In addition to winter sports, visitors can explore the natural beauty of the surrounding lakes and the nearby national state park. Great Barrington has a vibrant community atmosphere, with unique shops and eateries that add to its charm, making it an ideal spot for an active getaway.

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 from July to September, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudySlightly LowSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnyAverageAverage
December29.5°F (-1.4°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or review and organise your itineraries. You'll discover your saved or booked properties neatly organised into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical city of Stockbridge awaits you

Enjoy the area's museums, history and architecture with a rental holiday home in Stockbridge. Revered for its gardens, camping and hiking, this city is both romantic and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Stockbridge

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Stockbridge has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (7.2 mi / 11.6 km)
  • Bousquet Ski Area (9.1 mi / 14.6 km)
  • Catamount Ski Area (11.6 mi / 18.7 km)
  • Otis Ridge (12.9 mi / 20.8 km)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)
  • Greenock Country Club (3.4 mi / 5.5 km)

Exploring the natural features in Stockbridge

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Stockbridge. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Naumkeag Museum (0.3 mi / 0.4 km)
  • Berkshire Botanical Garden (1.2 mi / 2 km)
  • The Mount (3.8 mi / 6.2 km)
  • Housatonic River (6.6 mi / 10.5 km)
  • Housatonic River Walk (6.6 mi / 10.6 km)
  • Goose Pond Reservation (6.8 mi / 10.9 km)

Transport options to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.6 mi (15.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 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, Massachusetts, the ideal area to stay would be the picturesque downtown area. This charming neighbourhood is not only central but also offers a delightful mix of shops, restaurants, and cultural attractions. One of the highlights of staying here is the proximity to the Norman Rockwell Museum, which celebrates the works of the iconic American artist and provides a fascinating insight into his life and legacy. Another nearby gem is the beautiful Stockbridge Bowl, a serene lake great for swimming, kayaking, or simply enjoying a leisurely afternoon by the water.

In addition to the downtown area, the outskirts of Stockbridge provide a quieter, more rural experience. This region features a range of holiday rentals, often located amidst lush greenery, allowing visitors to fully embrace the tranquillity of the Berkshires. Staying here places you near the stunning hikes and natural beauty of the nearby Berkshire Mountains, great for outdoor enthusiasts.
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 areas for renting a beach house in Stockbridge?
For renting a beach house in Stockbridge, Massachusetts, the best areas to consider are along the scenic shores of nearby lakes, particularly Lake Mahkeenac. This picturesque setting offers a range of holiday rentals, including charming cottages and spacious family homes, many of which come with amenities such as private docks, outdoor decks, and fully equipped kitchens. These properties provide easy access to the water, superb for swimming, kayaking, or simply enjoying peaceful lake views.

In addition, the area around the Stockbridge Bowl is another excellent option, where visitors can find properties that often feature amenities like fire pits, screened porches, and expansive lawns for family gatherings. This location not only offers beautiful water access but also nearby walking trails and picnic spots, making it ideal for outdoor enthusiasts.
Where are the best Stockbridge ski resort rentals?
For the best ski resort rentals near Stockbridge, Massachusetts, travellers should consider the nearby area of Lenox and the picturesque town of Great Barrington, both of which provide convenient access to several ski areas. The Butternut Basin ski area, located just a short drive from Great Barrington, is particularly popular among families and beginners. Here, visitors can find a range of rental properties, including cosy chalets and cabins equipped with amenities such as fireplaces, ski storage, and outdoor spaces for enjoying the beautiful winter landscape.

In Lenox, you can discover charming inns and boutique hotels that offer a warm atmosphere, often featuring amenities like complimentary breakfast, spa services, and access to local art galleries and theatres. Many of these properties are located within the scenic Berkshires, allowing guests to enjoy not only skiing but also hiking trails and cultural attractions in the warmer months.
What is the most popular type of holiday rental accomodation in Stockbridge?
In Stockbridge, holiday houses are the most popular type of rental, with around 25 available throughout this charming town. Most of these houses are situated in picturesque neighbourhoods, providing easy access to local attractions like the Norman Rockwell Museum and the beautiful landscapes of the Berkshires. Guests can expect amenities such as fully equipped kitchens, spacious living areas, and often outdoor spaces for relaxation.
Are there any family house rentals in Stockbridge?
In Stockbridge, Massachusetts, there are some family-friendly house rentals available, with around 19 options to choose from. This charming town is known for its picturesque landscapes and cultural attractions, making it a wonderful destination for families. Many properties come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces that are great for children to play in. Additionally, amenities such as Wi-Fi and laundry facilities add to the convenience of your stay.
Can I rent a holiday home with a pool or hot tub in Stockbridge?
In Stockbridge, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the picturesque Berkshires, offers a serene setting great for relaxation. Many of these properties come with spacious outdoor areas, including private pools and hot tubs, ideal for unwinding after a day of exploring the local attractions.
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, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces like gardens or patios, ideal for relaxing after a day of exploration.

The town itself is steeped in natural beauty, with nearby attractions such as the picturesque Berkshire Mountains and the stunning Stockbridge Bowl, which offers opportunities for hiking, swimming, and picnicking. Additionally, the area features pet-friendly parks and trails, making it easy for pet owners to enjoy the outdoors with their pets.
Are there any remote work holiday rentals in Stockbridge?
In Stockbridge, Massachusetts, there are numerous remote work holiday rentals available, with around 29 options to choose from. This picturesque town, known for its stunning natural landscapes and cultural attractions, offers a variety of properties that cater to remote workers. Many of these rentals include essential amenities such as Wi-Fi, dedicated workspaces with desks and ergonomic chairs, and some even feature additional equipment like computer monitors to ensure a productive work environment. 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 fully equipped kitchens, which often feature appliances such as microwaves, stovetops, and dishwashers. These kitchens come complete with cookware and dishware, allowing guests to prepare meals during their stay. The availability of these amenities makes holiday rentals particularly appealing for families or groups who prefer the convenience of self-catering while enjoying the scenic beauty of the Berkshires and nearby attractions like the Norman Rockwell Museum and Tanglewood.
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 vibrant peak season from July to September. This period draws a lively crowd, as visitors flock to experience the rich cultural offerings, including art galleries, music festivals, and the picturesque landscapes of the Berkshires. The warm summer temperatures, typically ranging from 20 to 30 degrees Celsius, create an inclusive setting for outdoor activities such as hiking and exploring the charming downtown area.

July is particularly popular, as it showcases the height of summer festivities, making it a great time for families and groups looking to immerse themselves in local events and activities. The town's beautiful surroundings provide ample opportunities for scenic walks and leisurely picnics, allowing you to take in the stunning views of the rolling hills and lush greenery.

If you're keen on a more budget-friendly experience, consider visiting in January. While this is the low season, it offers its own unique charm—think serene winter landscapes and opportunities for cosy indoor activities, such as visiting local museums or enjoying a warm drink at a quaint café.
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, visitors can immerse themselves in a charming New England setting with several top attractions. The Norman Rockwell Museum, located along the Housatonic River, showcases a vast collection of the artist's works and offers insights into his life and legacy. Nearby, the picturesque Main Street is lined with quaint shops and local eateries, providing a delightful atmosphere for leisurely strolls.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

More holiday ideas