Photo by Elizabeth Massa Peroulakis

Chester holiday lettings

We found 117 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

August 2025

September 2025

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.

Holiday rentals with weekly discounts - Chester

Showing deals for:14 Nov - 21 Nov

Exceptional

(195 reviews)

The Clearing - Quiet - Close To Nature

Cummington, MA

13% off

£123 per night

includes taxes & fees

Exceptional

(171 reviews)

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

Peru, MA

12% off

£190 per night

includes taxes & fees

View from deck looking over our dock on a still day in last days of October.

Exceptional

(154 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

Otis, MA

16% off

£234 per night

includes taxes & fees

Exceptional

(24 reviews)

Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond

Becket, MA

7% off

£243 per night

includes taxes & fees

Coming down the driveway of our Berkshire Getaway!

Exceptional

(93 reviews)

Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!

Becket, MA

14% off

£261 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Chester

Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

Cozy Berkshires Vacation Rental Near Hiking!

Sleeps 6 · 2 bedrooms · 1 bathroom

Top rated rentals - Chester

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

Find out more about Chester

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:

Blandford Ski Area (6.6 mi / 10.6 km)
Otis Ridge (8.5 mi / 13.7 km)
Maple Corner Farm Cross Country Ski Area (10.7 mi / 17.1 km)
Wood's Pond (14.4 mi / 23.2 km)
Wyndhurst Golf & Club (15.4 mi / 24.7 km)
The Bookstore (16.5 mi / 26.6 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:

Glendale Falls (4.9 mi / 7.9 km)
Pyramid Lake (6.1 mi / 9.8 km)
Skyline Trail (6.6 mi / 10.6 km)
Otis Reservoir (9.4 mi / 15.1 km)
Tolland State Forest (9.8 mi / 15.8 km)
Goose Pond Reservation (10.7 mi / 17.2 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

What is the best area to stay in Chester when booking a holiday rental?

When considering a holiday rental in Chester, Massachusetts, a great area to stay in is the vicinity of the town centre. This charming area not only offers a quaint atmosphere but also places you within easy reach of local attractions. One great point of interest is the Chester Railway Station, which serves as a reminder of the town's rich history and is a lovely spot to explore. Additionally, the nearby Chester-Blandford State Forest provides excellent opportunities for hiking and enjoying the stunning natural scenery, making it great for outdoor enthusiasts.

How much does it cost to rent a holiday home in Chester?

Prices for holiday rentals in Chester 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 Chester 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 Chester holiday house rentals?

You can find great discounts on house rentals in Chester 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.

Can I find long-stay holiday rentals in Chester?

A long-stay holiday rental in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there any Chester holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Chester with parking available—perfect for families or travellers 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.

When is the best time to visit Chester for a holiday rental?

The best time to book a holiday rental in Chester is during the peak season from June to August, particularly in July. This vibrant period attracts nature enthusiasts and families looking to enjoy the warm summer weather, superb for outdoor activities such as hiking and exploring the scenic beauty of the nearby Berkshire Mountains.

During these summer months, you can expect temperatures in the mid to high 20s Celsius, providing an ideal climate for leisurely walks, picnics by the river, and enjoying the local parks. Chester's charming town centre also comes alive with various events and festivals, adding to the lively atmosphere that many visitors cherish.

For those seeking a more tranquil experience, consider visiting in November. This month offers a unique opportunity to witness the stunning autumn foliage as the leaves transition into vibrant shades of orange and red. The cooler temperatures create a crisp, refreshing environment for hiking and outdoor exploration, allowing you to appreciate Chester's natural beauty without the crowds.

How early should I book a Chester holiday rental?

Book your Chester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Chester home rental booking on Vrbo?

To find Chester holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Chester holiday 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.