West Stockbridge vacation rentals

We found 390 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 23 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.

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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 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:

  • 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)
  • Furnace Brook Winery at Hilltop Orchards (4.3 mi / 6.9 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:

  • Naumkeag Museum (4 mi / 6.5 km)
  • The Mount (4.3 mi / 7 km)
  • Housatonic River Walk (9.4 mi / 15.2 km)
  • October Mountain State Forest (10.5 mi / 17 km)
  • Pittsfield State Forest (10.7 mi / 17.2 km)
  • Bash Bish Falls State Park (16.7 mi / 26.9 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 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?

One of the more desired areas to find a West Stockbridge vacation home is Alford. When you lock in your vacation property with Vrbo, you'll enjoy having the entire place to yourself. This means you won't have to share it with anybody other than your favorite people.

What is the most popular type of vacation rental accommodation in West Stockbridge?

Houses are the most popular type of vacation rental in West Stockbridge, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in many shapes and sizes. Browse our options to find your perfect pad.

How much does it cost to rent a vacation rental in West Stockbridge?

Property type, length of stay and time of year are some of the conditions that can influence the price of a vacation home. Simply enter your travel dates to find your ideal fit. From cozy cabins to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.

How much does it cost to rent a beach house in West Stockbridge?

When you travel and the style and size of the property will influence the cost of your beachside escape. Put in your West Stockbridge travel dates to see all your options on Vrbo. Can't live without a private pool? Use the filters to pick the features and amenities you need.

Are there pet-friendly vacation rentals in West Stockbridge?

With 28 properties that welcome four-legged guests, your furry friend can join in on your West Stockbridge vacation. Use the filter tool to search our pet-friendly vacation rentals and find the pawfect pad on Vrbo.

Can I rent a house with a pool in West Stockbridge?

Check the "pool" box in our filter tool and select from four houses with private pools in West Stockbridge on Vrbo. Gentle soak, ball games or noodle joust? Downtime is up to you when your Vrbo vacation property comes with its own swimming pool.

What are popular rental amenities in West Stockbridge?

Some of the most popular rental amenities people look for in West Stockbridge include a sauna, a nearby river and a firepit. Whether you're taking a trip with buddies, family or even pets, Vrbo vacation rentals include the best amenities for beginning new traditions with your loved ones.

Are there large group vacation rentals in West Stockbridge?

West Stockbridge has five vacation properties that can host 10 or more guests. These stays come with the privacy and space you need to share good times with loved ones.

Are there vacation rentals in West Stockbridge that welcome kids?

With 28 family-friendly vacation properties to pick from in West Stockbridge, now is a fantastic time to introduce the kiddos to the excitement of travel. Just check our "Properties good for families" filter box to locate stays that feature conveniences ideal for vacationing families, such as extra bedrooms, pools, entertainment units and bunk beds.

What are the top attractions for families in West Stockbridge?

Keeping the kiddos entertained during your stay in West Stockbridge is a snap with these family-friendly attractions:

  • Berkshire Scenic Railway Museum
  • Arrowhead Museum
  • Norman Rockwell Museum

Can I find two-bedroom vacation rentals in West Stockbridge?

Gather your nearest and dearest and enjoy a relaxing escape in one of the four two-bedroom vacation rentals West Stockbridge has to offer.

Are there vacation rentals with WiFi in West Stockbridge?

You can choose from 11 vacation rentals with WiFi in West Stockbridge. If you'd like to disconnect from daily life on your vacation, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

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