West Stockbridge holiday lettings

We found 390 holiday 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 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.

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

  • 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 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?

One of the more desired areas to find a West Stockbridge holiday home is Alford. When you lock in your holiday 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 favourite people.

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

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

How much does it cost to rent a holiday 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 holiday home. Simply enter your travel dates to find your ideal fit. From cosy cabins to sprawling luxury villas, all Vrbo holiday 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 holiday rentals in West Stockbridge?

With 28 properties that welcome four-legged guests, your furry friend can join in on your West Stockbridge holiday. Use the filter tool to search our pet-friendly holiday 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 holiday 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 holiday rentals include the best amenities for beginning new traditions with your loved ones.

Are there large group holiday rentals in West Stockbridge?

West Stockbridge has five holiday 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 holiday rentals in West Stockbridge that welcome kids?

With 28 family-friendly holiday 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 holidaying 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 holiday rentals in West Stockbridge?

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

Are there holiday rentals with WiFi in West Stockbridge?

You can choose from 11 holiday rentals with WiFi in West Stockbridge. If you'd like to disconnect from daily life on your holiday, 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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