West Stockbridge holiday lettings

We found 460 holiday rentals — enter your dates for availability
Discover a selection of 21 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: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 £2,722
for 7 nights, 1 home
£389 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut

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

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:

  • 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)
  • Otis Ridge (16.7 mi / 26.8 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)
  • Queechy Lake (5.6 mi / 9 km)
  • Lenox Mountain (5.6 mi / 9.1 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 area surrounding the town centre is often regarded as the best option for visitors. This charming neighbourhood offers a delightful blend of tranquillity and accessibility to local attractions.

Staying near the centre allows you to easily explore the beautiful landscapes and cultural offerings of the region. One of the top attractions is the West Stockbridge Historical Society, which provides insights into the town's rich history and heritage. Additionally, the nearby Kripalu Centre for Yoga & Health is a fantastic spot for those looking to rejuvenate and indulge in wellness activities, set against the backdrop of the stunning Berkshires.

While the number of properties varies, this central area typically offers a range of holiday rentals, from quaint cottages to more spacious homes, suiting different preferences and group sizes.
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 areas for renting a beach house in West Stockbridge?
For renting a beach house in West Stockbridge, the area near the scenic shores of Stockbridge Bowl is a great option. This picturesque lake offers a tranquil setting with various rental properties that often feature amenities such as private docks, outdoor seating areas, and fully equipped kitchens, great for families or groups looking to enjoy a relaxing getaway by the water. Many homes in this vicinity provide stunning views of the lake and surrounding hills, enhancing the overall experience.

Additionally, the nearby town of Lenox, just a short drive away, has a selection of charming rentals that allow easy access to both the lake and cultural attractions. Properties here may include spacious outdoor decks, barbecues, and access to local hiking trails, making them ideal for outdoor enthusiasts. The proximity to local restaurants, shops, and the renowned Tanglewood Music Festival adds to the appeal for those looking to blend relaxation with cultural experiences.
Where are the best West Stockbridge ski resort rentals?
For skiing near West Stockbridge, the closest resorts are found in the nearby Berkshires, particularly at places like Butternut Basin and Jiminy Peak. In West Stockbridge itself, you can find charming accommodations that serve as a great base for these ski adventures. Many properties in the area are quaint, historic homes or modern cabins, often featuring amenities such as fully equipped kitchens, cosy fireplaces, and spacious living areas superb for relaxing after a day on the slopes.

In addition to the ski resorts, the surrounding region boasts a range of outdoor activities, including hiking and snowshoeing during the winter months. Properties in West Stockbridge often have easy access to local attractions, such as the picturesque Norman Rockwell Museum or the tranquil parks nearby. For guests seeking comfort, many rentals include essentials like Wi-Fi, heating, and laundry facilities, ensuring a convenient stay in this scenic part of Massachusetts.
What is the most popular type of holiday rental accomodation in West Stockbridge?
In West Stockbridge, holiday houses are the most popular type of holiday rental, with around 39 available throughout the area. These properties often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, superb for enjoying the serene surroundings. Additionally, there are about 12 cabins, which provide a rustic charm and a closer connection to nature, typically equipped with cosy interiors and sometimes even fireplaces. Several cottages and condos are also on offer, adding to the variety of options for visitors.
Are there any family house rentals in West Stockbridge?
In West Stockbridge, Massachusetts, there are some family-friendly house rentals available, offering a welcoming environment for groups. This charming town is known for its picturesque landscapes and proximity to attractions like the iconic Norman Rockwell Museum and the beautiful Berkshire Botanical Garden.

Many of the properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play. Visitors can also find amenities such as Wi-Fi and cosy fireplaces, superb for those cooler evenings.
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 excellent choice for those seeking relaxation and comfort during their stay. This picturesque town, located in the Berkshires, offers a serene environment with beautiful natural surroundings.

Travellers can expect various amenities in these properties, including private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens great for self-catering. Some rentals may also provide additional features such as fire pits and scenic views of the surrounding landscape, enhancing the overall holiday experience.
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, offering a delightful retreat for travellers accompanied by their furry companions. The area features charming properties with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely. Many holiday homes also include features like fenced yards and close proximity to local parks, making it convenient for dog owners to enjoy outdoor activities.

West Stockbridge is a picturesque town located in the Berkshires, surrounded by beautiful landscapes and opportunities for hiking and exploring nature. The nearby Beartown State Forest offers excellent trails for both pets and their owners, providing a fantastic backdrop for outdoor adventures.
Are there any remote work holiday rentals in West Stockbridge?
In West Stockbridge, there are numerous options for remote work holiday rentals, with around 63 available throughout the area. This quaint town in Massachusetts provides a serene backdrop for those looking to balance work and leisure. Many properties are equipped with essential amenities such as reliable Wi-Fi, dedicated desks, comfortable desk chairs, and even printers, ensuring a productive environment.

Guests can enjoy the charming atmosphere of West Stockbridge, which is home to lovely art galleries, local shops, and picturesque landscapes. The nearby Beartown State Forest offers opportunities for outdoor activities, superb for unwinding after a day of work. 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 include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios for enjoying the serene surroundings. Many properties also feature fireplaces, superb for cosy evenings after a day of exploring the area. Onsite parking is commonly available, providing convenience for those travelling by car. Additionally, most rentals offer coffee and tea makers, ensuring that guests can start their mornings with a warm beverage.
When is the best time to visit West Stockbridge for a holiday rental?
The peak season in West Stockbridge runs from July to September, making it the most popular time for holiday rentals in this charming Massachusetts town. During these months, visitors flock to the area to enjoy the vibrant arts scene, outdoor activities, and the stunning natural beauty of the Berkshires. The warm summer temperatures, typically ranging from 20 to 30 degrees Celsius, create an inviting environment for sightseeing, hiking, and exploring local attractions.

July, in particular, is a highlight for many travellers. With lush green landscapes and a buzzing atmosphere, it's the great time to experience outdoor festivals, local farmers' markets, and cultural events that capture the essence of this picturesque region. The proximity to various hiking trails and scenic spots makes it ideal for those who enjoy a blend of adventure and relaxation.

For those looking for a more budget-friendly option, consider visiting in December. While this month falls outside the high tourist season, it offers a unique charm with a quieter ambiance, beautiful winter scenery, and opportunities for cosy indoor activities. Plus, you can enjoy the festive spirit of the holiday season in a serene setting, great for a peaceful getaway.

Ultimately, the best time to visit West Stockbridge depends on your holiday preferences—whether you crave the lively summer atmosphere or the tranquil charm of wintertime.
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.
What are the top attractions in West Stockbridge?
In West Stockbridge, visitors can take part in the charming New England atmosphere while exploring local attractions. The town is renowned for its picturesque landscapes and art scene, particularly at the renowned Norman Rockwell Museum located nearby in Stockbridge, which celebrates the iconic American artist's work.

Nature enthusiasts will appreciate the scenic beauty of the nearby Berkshire Hills, offering opportunities for hiking and outdoor activities. The area's quaint downtown features local shops and galleries, where visitors can discover unique crafts and artworks. Additionally, West Stockbridge is conveniently located close to the cultural offerings of the Berkshires, including Tanglewood, the summer home of the Boston Symphony Orchestra, which is just a short drive away.

The town's historical charm is evident in its well-preserved architecture, and visitors can enjoy leisurely strolls along the main street, taking in the local vibe.
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 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 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.
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.

More holiday ideas