West Stockbridge vacation rentals

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Discover a selection of 21 homes and other vacation rentals in West Stockbridge that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, including parking and a garden. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - West Stockbridge

Showing deals for:Apr 24 - May 1

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is $328
$2,296 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington

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Find out more about West Stockbridge

Why visit West Stockbridge

  • Charming Historic Sites: Explore picturesque historic houses that reflect the town's rich heritage.
  • Scenic Outdoor Spaces: Enjoy breathtaking views in nearby national and state parks, perfect for outdoor enthusiasts.
  • Cultural Experiences: Immerse yourself in local arts and cultural activities that enrich your visit.
  • Family-Friendly Attractions: Discover activities suitable for all ages, making it an ideal destination for families.
  • Cozy Accommodations: Choose from a range of vacation rentals, from charming cottages to comfortable motels.

Popular types of accommodation in West Stockbridge

If you're planning a getaway to West Stockbridge, you're in luck. Our vacation rentals offer a variety of popular accommodations, including houses, cozy cottages, and comfortable condos. For those seeking a more traditional stay, the Pleasant Valley Motel provides a welcoming atmosphere. Whatever your preference, West Stockbridge has the perfect spot for you to unwind and explore the beauty of this charming area.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy in West Stockbridge, perfect for families or groups.
  • Condos: Ideal for those who enjoy modern amenities and shared facilities, condos offer a convenient stay in the heart of West Stockbridge.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, often surrounded by nature, making them a popular choice.
  • Apartments: Offering flexibility and independence, apartments are great for solo travelers or couples looking for a home away from home.
  • Cabins: Set in picturesque settings, cabins are favored by those wanting a rustic experience amidst the beauty of West Stockbridge.**

Top attractions near West Stockbridge

West Stockbridge, Massachusetts, offers a delightful blend of romantic and cultural experiences, perfect for entertainment-themed vacations. Visitors can explore historic houses, enjoy the natural beauty of national and state parks, and discover local preserves. The area caters to those seeking outdoor adventures, family-friendly activities, and rich cultural experiences. Don't miss the chance to visit local attractions that enhance your stay in this charming town.

  • National Shrine of the Divine Mercy: A serene and spiritual destination, this shrine offers a peaceful atmosphere for reflection and prayer, surrounded by beautiful gardens and stunning architecture, just 4 miles from West Stockbridge.
  • Norman Rockwell Museum: Celebrate the iconic American artist Norman Rockwell through his captivating illustrations and paintings, housed in a charming museum featuring engaging exhibits and a lovely outdoor area, also 4 miles away.
  • The Mount: The former home of author Edith Wharton, this historic estate showcases exquisite architecture and beautiful gardens, offering a glimpse into the life of this literary icon, located 4 miles from West Stockbridge.

Things to do recommended for couples

For a romantic getaway in West Stockbridge, enjoy a concert at Tanglewood Music Center, only 3 miles away. Embrace the thrill of skiing at Bousquet Ski Area, 7 miles distant, or savor exquisite wines at Furnace Brook Winery, just 4 miles away, perfect for a cozy afternoon.

Things to do recommended for families

Families visiting West Stockbridge can enjoy the serene vibes of Kennedy Park, just 6 miles away, and Lake Mansfield Park, 9 miles away. Don't miss Fairfield Brook WMA, located 4 miles away, offering a peaceful retreat and engaging outdoor activities for everyone.

Things to do recommended for groups

In West Stockbridge, your group can enjoy a captivating performance at Shakespeare and Company, just 5 miles away, or shop at the charming Charles H. Baldwin & Sons. For outdoor enthusiasts, Wyndhurst Golf & Club, also 5 miles away, offers a perfect spot for a friendly game of golf.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with friends, family, pets, or are seeking extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to West Stockbridge with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to West Stockbridge with young kids: Traveling with young kids can be quite demanding. It’s important to prioritize their comfort and safety, along with finding 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 West Stockbridge: For many families, a vacation just isn’t the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most 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 West Stockbridge: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near West Stockbridge

West Stockbridge, Massachusetts, offers a charming blend of entertainment, romance, and cultural experiences. Nestled in a prime location, this picturesque town is perfect for budget-friendly getaways or romantic retreats. Visitors can explore nearby family-friendly attractions, savor scenic views, and enjoy a relaxing atmosphere. With a variety of hotels and accommodations available, West Stockbridge is an ideal base for discovering the beauty and vibrancy of the Berkshires region.

  • Lenox: Located 5 miles from West Stockbridge, Lenox is a charming city that draws visitors for its vibrant entertainment scene and romantic settings, making it ideal for family-friendly outings. The area is renowned for its music concerts and theatrical performances, often held in beautiful venues that enhance the cultural experience. Outdoor enthusiasts can enjoy nearby lakes and mountains, which provide perfect backdrops for recreation year-round. In the winter, skiing opportunities abound, while the summer welcomes visitors to explore lush trails and local events.
  • Stockbridge: Just 4 miles from West Stockbridge, Stockbridge is a culturally rich city that offers a blend of romance and entertainment. Known for its artistic vibe, the city features theaters and concert venues that highlight local talent and renowned artists alike. Attractions like serene lakes and historical monuments, including famous shrines, invite exploration and reflection. Stockbridge is also home to cultural festivals and events that showcase the town's heritage, ensuring visitors experience a unique blend of art, history, and natural beauty.
  • Lee: Situated 6 miles from West Stockbridge, Lee is a delightful city that appeals to families, couples, and entertainment seekers. With its inviting theaters and lively music concerts, Lee is a great spot for enjoying a night out. The city is surrounded by picturesque landscapes featuring lakes, mountains, and historical monuments, creating a scenic escape. Whether you're skiing in the winter or participating in local events during the summer, Lee offers a warm and welcoming atmosphere for all visitors to enjoy.

Best time to go to West Stockbridge

If you're planning a trip to West Stockbridge, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudyModerately LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly 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 SunnyModerately HighAverage
July70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnyAverageSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyModerately HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnyModerately LowAverage
December29.5°F (-1.4°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking an extended stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect fit for your travel needs.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. It's truly beneficial to be the trip planner. Become a member of our One Key rewards program to enjoy exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous arrangements, or manage your travel itinerary. You'll easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To start utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around West Stockbridge

Are you hoping to discover things to do during your stay? Venture out of your cozy vacation rental and check out everything that West Stockbridge has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 an adventurous traveler or just want to take in the scenery, West Stockbridge is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Housatonic River (9.4 mi / 15.2 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 center. If you can't find a flight that works for your travel itinerary, you could also fly 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 vacation rental?
When booking a vacation rental in West Stockbridge, one of the best areas to consider is the charming downtown district. This area is not only picturesque but also conveniently located near various local attractions and amenities. Staying here allows you to easily explore the delightful shops, art galleries, and quaint eateries that line the streets. The downtown district often has a selection of vacation rentals, ranging from cozy cottages to more spacious homes, giving visitors plenty of options.

A highlight of this area is the West Stockbridge Historical Society, which offers insights into the region's rich history. Additionally, the nearby Berkshire Botanical Garden is a must-visit for nature enthusiasts, showcasing stunning landscapes and beautiful plant collections.
How much does it cost to rent a vacation home in West Stockbridge?
Prices for vacation 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 vacation 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, consider the nearby areas of Lenox and Great Barrington, which are within a short drive and provide convenient access to popular ski destinations like Jiminy Peak. In Lenox, visitors can find charming rental homes and cozy cabins that often come equipped with amenities such as wood-burning stoves, spacious living areas, and outdoor decks for enjoying the beautiful Berkshire landscape. Many properties in this area are designed for groups or families, featuring multiple bedrooms and fully equipped kitchens for self-catering.

In Great Barrington, the rental options are diverse, including modern condos and traditional New England-style homes. These properties frequently offer amenities like hot tubs, game rooms, and proximity to local shops and eateries, enhancing the overall experience for travelers. The town also provides access to scenic outdoor activities during both winter and summer, with hiking trails and local parks nearby.

Additionally, the region's artistic and cultural scene, showcased through galleries and live performances, adds a unique touch to the ski vacation experience.
What is the most popular type of vacation rental accomodation in West Stockbridge?
In West Stockbridge, vacation houses are the most popular type of accommodation, with around 14 available in the area. These houses typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a cozy feel. Additionally, there are several cabins and cottages scattered throughout the picturesque countryside, providing a rustic charm and a closer connection to nature. These properties often feature outdoor spaces for relaxation, such as decks or patios, great for enjoying the serene surroundings. Some condos are also available, typically offering modern amenities and convenient access to local attractions.
Are there any family house rentals in West Stockbridge?
In West Stockbridge, Massachusetts, there are numerous family-friendly house rentals available—around 22 in total. This charming town offers a serene setting with easy access to both outdoor activities and cultural attractions. Many of these homes provide spacious living areas, fully equipped kitchens for family meals, and outdoor spaces ideal for children to play. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.

Nearby, families can explore the picturesque landscapes of the Berkshires, with opportunities for hiking, biking, and enjoying the natural beauty of the area. Additionally, cultural highlights such as the Norman Rockwell Museum and Tanglewood, the summer home of the Boston Symphony Orchestra, are just a short drive away.
Can I rent a vacation home with a pool or hot tub in West Stockbridge?
In West Stockbridge, there are several vacation homes available for rent that feature pools and hot tubs, making it an inviting destination for travelers seeking relaxation and leisure. This charming town, located in the scenic Berkshires, provides a tranquil setting with easy access to outdoor activities and cultural attractions. Many properties come equipped with private pools, spacious outdoor decks, and hot tubs, superb for unwinding after a day of exploring the area.

Travelers can also expect amenities such as fully equipped kitchens, cozy living spaces, and sometimes fire pits or barbecue grills for outdoor gatherings. The picturesque surroundings offer opportunities for hiking, visiting local art galleries, and enjoying the vibrant dining scene nearby.
Can I find long-stay vacation rentals in West Stockbridge?
A long-stay vacation rental in West Stockbridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in West Stockbridge?
In West Stockbridge, there are several pet-friendly house rentals available, providing a cozy and welcoming atmosphere for travelers with pets. Many of these rentals feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. The area offers a peaceful, rural setting with stunning views of the surrounding hills and easy access to outdoor activities.

Additionally, West Stockbridge is near several parks and outdoor spaces where pets are welcome. The nearby Berkshire Botanical Garden and the scenic trails of the Appalachian Trail offer a great opportunity for walks and exploration with your furry companions.
Are there any remote work vacation rentals in West Stockbridge?
In West Stockbridge, there are numerous vacation rentals suitable for remote work, with around 24 options available. This charming town, located in the Berkshires, offers a peaceful environment ideal for productivity. Many of these properties come equipped with dedicated workspaces, including desks and comfortable chairs, alongside essential amenities such as Wi-Fi and computer monitors, ensuring a conducive atmosphere for working remotely.

Travelers can enjoy the scenic beauty of the area, with nearby attractions such as the Norman Rockwell Museum and the picturesque landscapes of the surrounding mountains. Additionally, the town's quaint shops and local dining options provide convenient breaks during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any West Stockbridge vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in West Stockbridge with parking available—perfect for families or travelers 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 WiFi, kitchens, patios, coffee and tea makers, and blenders. These features enhance the comfort and convenience of stays, allowing travelers to stay connected, prepare meals, and enjoy outdoor spaces.
When is the best time to visit West Stockbridge for a vacation rental?
The best time to visit West Stockbridge for a vacation rental is during the peak season from July to September. This vibrant period attracts travelers seeking a mix of outdoor activities, cultural events, and the stunning natural beauty of the Berkshires. July, in particular, is a highlight, as the warm weather (typically ranging from the mid-60s to mid-80s Fahrenheit) invites visitors to enjoy hiking, art festivals, and local markets.

During these summer months, the area buzzes with tourists, offering a lively atmosphere great for those who thrive in social settings and appreciate community events. West Stockbridge is known for its charming downtown, where you can explore unique shops, indulge in delicious local cuisine, and attend outdoor concerts.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is less crowded, it provides a wonderful opportunity to experience the tranquil beauty of the Berkshires in winter. Enjoy cozy stays and the chance to partake in winter activities like cross-country skiing and holiday festivities.

Ultimately, your ideal time to visit West Stockbridge will depend on whether you prefer the lively summer scene filled with activity or the peaceful charm of the winter months.
How early should I book a West Stockbridge vacation rental?
Book your West Stockbridge vacation 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 vacation 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 enjoy a charming mix of natural beauty and cultural attractions. The town is known for its picturesque landscapes and access to outdoor activities. Nearby, the historic Norman Rockwell Museum in Stockbridge showcases the artist's work and is a must-visit for art enthusiasts. For nature lovers, the nearby Berkshire Botanical Garden offers beautiful gardens and trails for leisurely walks.

West Stockbridge itself features quaint shops and local dining options, providing an authentic small-town experience.
Can I change or cancel my West Stockbridge home rental booking on Vrbo?
To find West Stockbridge vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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