West Stockbridge holiday lettings

We found 426 holiday rentals — enter your dates for availability

Discover a selection of 19 homes and other holiday rentals in West Stockbridge that are perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - West Stockbridge

Showing deals for:6 Feb - 13 Feb

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington, MA

8% off
Price is £1,958
for 7 nights, 1 cottage
£280 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

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The charming area of West Stockbridge awaits your stay

The gardens, forests and lake display a scene truly unique to West Stockbridge. Well known for its wildlife, restaurants and yoga, this romantic city won't disappoint. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around West Stockbridge

Are you searching for top things to see and do while you're in the area? Venture out of your holiday home and check out everything that West Stockbridge has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Furnace Brook Winery at Hilltop Orchards (4.3 mi / 6.9 km)
  • Wyndhurst Golf & Club (5.2 mi / 8.3 km)
  • Bousquet Ski Area (7.2 mi / 11.6 km)
  • Ski Butternut (10.7 mi / 17.2 km)
  • Catamount Ski Area (12.9 mi / 20.7 km)
  • Jiminy Peak Mountain Resort (15.8 mi / 25.4 km)

Exploring the natural landscape of West Stockbridge

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in West Stockbridge. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Stockbridge Bowl (2.5 mi / 4 km)
  • Berkshire Botanical Garden (2.8 mi / 4.5 km)
  • Naumkeag Museum (4 mi / 6.5 km)
  • The Mount (4.3 mi / 7 km)
  • Pleasant Valley Wilderness Sanctuary (5.4 mi / 8.7 km)
  • Queechy Lake (5.6 mi / 9 km)

How to get to and around West Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 7.4 mi (11.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away.

Frequently asked questions

What is the best area to stay in West Stockbridge when booking a holiday rental?
When considering a holiday rental in West Stockbridge, Massachusetts, the quaint and picturesque village centre is a popular area to stay. This charming neighbourhood offers a delightful blend of local shops, art galleries, and eateries that reflect the town's artistic spirit and rich history. The proximity to the West Stockbridge Historical Society and the beautifully preserved architecture enhances the cultural experience, making it an ideal spot for those interested in exploring the local heritage.

Another appealing area is along the scenic Route 41, where you can find properties that offer tranquil views of the surrounding countryside. This location is great for nature lovers, as it provides easy access to outdoor activities such as hiking and biking. Additionally, being close to the renowned Tanglewood Music Centre, which hosts a variety of performances throughout the summer, makes it a prime choice for music enthusiasts.
How much does it cost to rent a holiday home in West Stockbridge?
Prices for holiday rentals in West 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 West 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 West Stockbridge holiday house rentals?
You can find great discounts on house rentals in West 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 West Stockbridge ski resort rentals?
For ski resort rentals near West Stockbridge, Massachusetts, travellers should consider the nearby area of Lenox, which is approximately a 20-minute drive from the popular ski slopes of Jiminy Peak. In Lenox, you can find a variety of charming lodges and holiday homes that cater to winter sports enthusiasts. Many of these properties come with amenities such as heated pools, hot tubs, and spacious living areas, superb for unwinding after a day on the slopes.

In addition to Lenox, the quaint village of Stockbridge itself offers a selection of cosy cottages and inns, where you can enjoy a more intimate experience. These accommodations often feature rustic interiors, fireplaces, and fully equipped kitchens, allowing for a comfortable stay. The proximity to local restaurants and shops adds to the convenience for travellers.
What is the most popular type of holiday rental accomodation in West Stockbridge?
In West Stockbridge, holiday houses are the most popular type of rental accommodation, with approximately 18 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many houses also come with outdoor areas, such as patios or gardens, allowing guests to enjoy the serene surroundings. Additionally, there are several cabins and cottages available, which provide a more rustic experience and often include amenities like wood-burning stoves and picturesque views of the natural landscape. Condos are also an option, offering a more compact living space with access to shared facilities.
Are there any family house rentals in West Stockbridge?
In West Stockbridge, Massachusetts, families will find a variety of holiday rentals—about 24 options are available in the area. This charming town is surrounded by natural beauty and cultural attractions, making it an ideal spot for family getaways. Many homes offer spacious layouts, with multiple bedrooms and comfortable living areas, superb for gathering after a day of exploring.

Visitors can expect amenities such as fully equipped kitchens, allowing for convenient meal preparation, as well as outdoor spaces where children can play and families can enjoy al fresco dining. Air conditioning and Wi-Fi are typically included, ensuring a comfortable stay.
Can I rent a holiday home with a pool or hot tub in West Stockbridge?
In West Stockbridge, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing destination for travellers seeking relaxation. This quaint town in the Berkshires offers a peaceful atmosphere, surrounded by beautiful natural scenery. Many of the properties come with amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, which are great for enjoying warm summer days or unwinding after a day of exploring the local attractions.
Can I find long-stay holiday rentals in West Stockbridge?
A long-stay holiday rental in West 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 West Stockbridge?
In West Stockbridge, there are several pet-friendly house rentals available, with a total of 13 options to choose from. This charming town is located in the picturesque Berkshires, providing a great getaway for travellers with pets. Many of the holiday rentals come equipped with essential amenities, including well-appointed kitchens, spacious living rooms, and outdoor areas that are ideal for pets to roam.
Are there any remote work holiday rentals in West Stockbridge?
In West Stockbridge, there are numerous remote work holiday rentals available, with around 28 options to choose from. This picturesque town, located in the Berkshires, offers a tranquil setting ideal for those seeking to blend work and leisure. Many properties come equipped with dedicated office spaces, high-speed Wi-Fi, and essential amenities such as desk chairs and computer monitors, ensuring a comfortable and productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any West Stockbridge holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in West 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 West Stockbridge?
In West Stockbridge, popular rental amenities primarily centre around the convenience of home-like features. Most holiday rentals come equipped with a kitchen, allowing guests to prepare their own meals. Additionally, amenities such as cookware, dishware, and utensils are commonly provided, ensuring a fully functional cooking space. Many rooms also include a refrigerator and a microwave, making it easy to store and heat up meals.
When is the best time to visit West Stockbridge for a holiday rental?
July is the most popular time to visit West Stockbridge, as it aligns with the peak season running from July to September. During these summer months, the charming town comes alive, offering a wealth of outdoor activities and cultural experiences. Visitors can enjoy the picturesque landscapes, visit local art galleries, and partake in seasonal festivals that showcase the vibrant community spirit.

July boasts warm temperatures, typically reaching the mid-20s Celsius, making it ideal for exploring the beautiful Berkshire Hills. Whether you're hiking nearby trails or simply strolling through the quaint streets, the pleasant weather enhances your outdoor adventures and sightseeing opportunities.

If you're considering a more budget-friendly option, December is a lovely time to visit West Stockbridge, where you can enjoy a quieter atmosphere. While the temperatures drop to around 0°C, the town's winter charm, with its festive decorations and peaceful surroundings, offers a great experience, superb for those seeking a cozy retreat.
How early should I book a West Stockbridge holiday rental?
Book your West 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.
Can I change or cancel my West Stockbridge home rental booking on Vrbo?
To find West 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 West 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.

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