Chester Vacation Rentals, Massachusetts: house rentals & more

Scroll through and select from vacation rentals in Chester to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find the best place to stay - Chester

The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History

Sleeps 20 · 6 bedrooms · 5 bathrooms

Blue door - entrance to the front house. Walkway on left leads to back house.

In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing

Sleeps 24 · 12 bedrooms · 7+ bathrooms

Find spaces that suit your style

Top rated rentals - Chester

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Artsy Chester will entice you

The area's theater scene and monuments are just a few of the reasons to vacation in Chester. This city's hiking, camping and waterfalls draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Chester

Do you want to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Chester has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

Wyndhurst Golf & Club (15.4 mi / 24.7 km)
Bousquet Ski Area (18 mi / 29 km)
Otis Ridge (8.5 mi / 13.7 km)
Kennedy Park (16.7 mi / 26.9 km)
Blandford Ski Area (6.6 mi / 10.6 km)
Maple Corner Farm Cross Country Ski Area (10.7 mi / 17.1 km)

Exploring the natural landscape of Chester

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Chester. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

Otis Reservoir (9.4 mi / 15.1 km)
October Mountain State Forest (10.2 mi / 16.5 km)
Goose Pond Reservation (10.7 mi / 17.2 km)
Look Memorial Park (15.5 mi / 25 km)
The Mount (16 mi / 25.8 km)
Smith College Botanic Garden (17.5 mi / 28.2 km)

Transportation to and around Chester

The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 15.4 mi (24.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away.

Frequently asked questions

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

Property type, length of stay and time of year are among the factors that can affect the price of a vacation home. Simply click on your dates of travel to find your dream escape. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals provide incredible value.

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

Prices for beach houses in Chester vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your rental options and prices. From there you can use our filter tool to refine your search by amenities, nearby activities, ratings and more.

What are the top attractions for families in Chester?

Blandford Ski Area will keep the kids entertained during a trip to Chester. This family-friendly attraction is located near the center.

How old do you have to be to rent a vacation rental in Chester?

We recommend you check with the Chester vacation property you'd like on Vrbo as the minimum age differs. However, generally it's 16, 18 or 21.

How long can I rent a vacation rental in Chester for?

The amount of time you can stay in a Chester vacation rental for is up to each property. Simply enter your dates of travel to view options offering longer term stays. They feature all you require to make your extended vacation more enjoyable and comfortable, like kitchens and backyards. Some Vrbo vacation homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.