Stockbridge holiday lettings

We found 774 holiday rentals — enter your dates for availability
Discover a selection of 33 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:9 Oct - 16 Oct

Image gallery for A Fun Farmhouse Near Ski Butternut

Exterior
10 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

7% off
Price is £2,726
for 7 nights, 1 home
£389 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut

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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:

  • Wyndhurst Golf & Club (4.7 mi / 7.6 km)
  • 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)

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)
  • Lake Mansfield Park (6.2 mi / 9.9 km)
  • Housatonic River (6.6 mi / 10.5 km)
  • Housatonic River Walk (6.6 mi / 10.6 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 charming neighbourhood of Stockbridge itself is a fantastic choice. This area is steeped in history and offers a delightful blend of natural beauty and cultural attractions. One of the top highlights is the Norman Rockwell Museum, which celebrates the works of the iconic American illustrator and provides a fascinating insight into his life and art. Additionally, the serene landscape of the Berkshire Mountains surrounding Stockbridge offers ample opportunities for outdoor activities, such as hiking and enjoying scenic vistas.

Another appealing area is nearby Lenox, which is just a short drive away and known for its vibrant arts scene. In Lenox, you can explore the Tanglewood Music Festival, a renowned summer venue for classical music, attracting visitors from all over. This neighbourhood also boasts lovely shops and restaurants, making it a delightful place to spend your evenings after a day of exploring.

In terms of holiday rentals, Stockbridge has a variety of properties, ranging from quaint cottages to more spacious homes, allowing visitors to choose what best suits their needs.
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, the picturesque areas surrounding Stockbridge Bowl are ideal. This serene lake offers a range of holiday rentals, from charming cottages to larger family homes, all with stunning views of the water. Many properties in this area come equipped with amenities such as private docks, outdoor seating areas, and fully stocked kitchens, great for enjoying leisurely meals while taking in the natural beauty.

In addition, the nearby areas of Lenox and Great Barrington provide further options for those looking to immerse themselves in the beauty of the Berkshires. Rentals here often feature spacious living areas, outdoor patios, and access to communal amenities such as swimming pools or walking trails. These towns are known for their vibrant arts scene, with local galleries and theatres, adding an enriching cultural experience to any stay.

For outdoor enthusiasts, the region offers numerous hiking trails and scenic spots, with some properties allowing easy access to local parks and nature reserves.
Where are the best Stockbridge ski resort rentals?
For ski resort rentals near Stockbridge, Massachusetts, the nearby town of Lenox offers excellent options, as it is conveniently located just a short drive from the slopes at Butternut Ski Area. Many rentals in this region are charming cottages or modern homes that typically feature amenities such as fully equipped kitchens, cosy living rooms with fireplaces, and outdoor spaces for relaxation.

In addition, Stockbridge itself has several quaint inns and bed-and-breakfasts that provide a more intimate lodging experience, often with beautifully appointed rooms and communal areas where guests can unwind after a day on the mountain. Some properties may include breakfast, local dining recommendations, and easy access to the cultural attractions of the Berkshires, such as Tanglewood and the Norman Rockwell Museum.

For those looking to enjoy both skiing and the scenic beauty of the area, rentals in nearby Great Barrington offer a vibrant arts scene and outdoor activities. Many properties there come with amenities like hot tubs, fire pits, and proximity to local shops and restaurants, making them ideal for groups or families who want to mix leisure with adventure.
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 around 88 available throughout the area. These properties are often set in picturesque surroundings, providing a charming escape for visitors. Most holiday houses come equipped with amenities such as full kitchens, spacious living areas, and outdoor spaces like decks or gardens, superb for enjoying the tranquil atmosphere. Additionally, there are about 20 cottages which offer a quaint, rustic experience, often featuring unique character and cosy interiors. For those seeking a more compact option, several condos and apartments can also be found, typically located near local attractions such as the Norman Rockwell Museum and the scenic Berkshire mountains.
Are there any family house rentals in Stockbridge?
In Stockbridge, Massachusetts, families will find a variety of holiday rentals—there are 19 available throughout the area. This picturesque town is known for its charming New England atmosphere and scenic landscapes, making it an excellent choice for family getaways. Many properties offer spacious living areas, fully equipped kitchens, and outdoor spaces where children can play and families can gather.

Visitors can enjoy amenities such as Wi-Fi, air conditioning, and sometimes even features like fireplaces or patios for outdoor dining. The town is conveniently located near attractions like the Norman Rockwell Museum, which celebrates the famous artist's work, and the beautiful hiking trails of the nearby Berkshire Mountains.
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 or hot tubs. This picturesque town, located in the Berkshires, offers a serene setting superb for relaxation. Many of the available properties come with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the beautiful surroundings during warmer months. Inside, guests can expect well-equipped kitchens, comfortable living spaces, and amenities like Wi-Fi and air conditioning, ensuring a pleasant stay.
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, making it an excellent choice for travellers looking to enjoy a getaway with their furry companions. Many of these holiday homes come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.

The charming town is surrounded by beautiful natural scenery, with easy access to outdoor activities that are superb for pet owners. Nearby, the picturesque Berkshire Mountains offer a variety of trails for hiking, allowing you and your pet to explore the stunning landscapes together. Additionally, Stockbridge is close to several pet-friendly parks, giving you ample opportunities for leisurely walks and outdoor playtime.
Are there any remote work holiday rentals in Stockbridge?
In Stockbridge, Massachusetts, there are numerous holiday rentals suitable for remote work, with around 100 options available. The area is known for its picturesque New England charm and cultural heritage, making it an appealing destination for those looking to blend work and leisure. Many rentals come equipped with essential amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable seating, ensuring a productive environment.

Travellers will find properties ranging from quaint cottages to spacious homes, often featuring inviting living areas, fully equipped kitchens, and outdoor spaces superb for a refreshing break. The town itself offers a variety of local attractions, including art galleries and historical sites, which can provide a welcome distraction after a day's work. 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 include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties feature decks or patios, providing spaces to enjoy the beautiful surroundings. A fireplace can often be found in these rentals, creating a warm and inviting atmosphere, particularly during the cooler months. Onsite parking is typically available, making it convenient for those travelling by car. Some rentals even come with a blender, great for making smoothies or other beverages.
When is the best time to visit Stockbridge for a holiday rental?
July marks the peak season for holiday rentals in Stockbridge, where visitors flock to enjoy the charm of this picturesque Massachusetts town. This time of year is particularly vibrant, with a wealth of outdoor activities and cultural events, making it superb for those seeking a blend of relaxation and adventure. The warm summer weather, typically ranging from 15 to 30 degrees Celsius, creates an ideal environment for exploring the scenic beauty of the Berkshire Mountains or taking leisurely strolls through the lush gardens of the Norman Rockwell Museum.

As the summer progresses into August and September, Stockbridge continues to thrive with tourists, offering a lively option filled with festivals and art shows. However, those looking for a quieter experience may find the low season in January to be appealing. While the winter months bring colder temperatures, averaging around -5 to 5 degrees Celsius, they also offer a serene beauty in the snow-covered landscapes, superb for cosy retreats.

For travellers seeking good value, visiting Stockbridge in the early spring months of April and May can be an excellent choice. The weather is mild, and the natural beauty begins to awaken, making it a great time for hiking and enjoying the blossoming flora without the summer crowds.
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 enjoy a blend of natural beauty and cultural attractions. The Norman Rockwell Museum, located in the town, showcases a vast collection of the artist's works and offers insights into American culture through his lens. The picturesque Main Street is lined with charming shops and eateries, superb for a leisurely stroll.

Just a short drive away, the Berkshire Botanical Garden provides a serene setting with beautiful landscaped gardens, ideal for nature lovers. For those interested in outdoor activities, the nearby Stockbridge Bowl offers opportunities for swimming, kayaking, and hiking along its scenic trails.
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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