Chester holiday rentals, Massachusetts: holiday houses & more

Scroll through and select from holiday rentals in Chester to find one that's perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, including Wi-Fi and parking. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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

House

Condo/Apartment

Top rated rentals - Chester

Premier Host

Always Perfect

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

Theatrical Chester will entice you

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

Activities and attractions in Chester

Are you hoping to find attractions to see while you're in town? Venture out of your holiday home and experience everything that Chester has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

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 an adventurous traveller or just want to appreciate the scenery, Chester is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

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)

Transport to and around Chester

The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 15.4 mi (24.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 holiday rental in Chester?

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

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

We recommend you check with the Chester holiday 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 holiday rental in Chester for?

The amount of time you can stay in a Chester holiday 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 holiday more enjoyable and comfortable, like kitchens and backyards. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.