Photo by Chris Addams

Chester holiday lettings

We found 118 holiday rentals — enter your dates for availability

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 spaces that suit your style

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:

  • Otis Ridge (8.5 mi / 13.7 km)
  • Maple Corner Farm Cross Country Ski Area (10.7 mi / 17.1 km)
  • Wyndhurst Golf & Club (15.4 mi / 24.7 km)
  • Kennedy Park (16.7 mi / 26.9 km)
  • The Ranch Golf Club (16.9 mi / 27.2 km)
  • Bousquet Ski Area (18 mi / 29 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:

  • Pyramid Lake (6.1 mi / 9.8 km)
  • Chesterfield Gorge (9.4 mi / 15.1 km)
  • Otis Reservoir (9.4 mi / 15.1 km)
  • Goose Pond Reservation (10.7 mi / 17.2 km)
  • Swift River (13.9 mi / 22.3 km)
  • Look Memorial Park (15.5 mi / 25 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 the best area to stay in Chester, Massachusetts, a fantastic choice would be the vicinity around the town centre. This charming area offers a delightful blend of local character and access to beautiful natural surroundings. You'll find a selection of holiday rentals that cater to various tastes and budgets, making it convenient for visitors looking for a home away from home.

One of the highlights of staying in this area is the proximity to the stunning Chester-Blandford State Forest, where you can enjoy a wealth of outdoor activities, including hiking and birdwatching. The tranquil beauty of the forest provides a superb backdrop for relaxation and adventure alike. Additionally, the nearby historic sites and quaint local shops add to the area's appeal, allowing you to immerse yourself in the community's rich heritage.
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.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, apartments are the most popular type of holiday rental, with several available throughout the area. These rentals typically provide a comfortable and homely atmosphere, often featuring fully equipped kitchens, cosy living areas, and modern amenities for convenience. Many apartments also come with outdoor spaces, allowing guests to enjoy the picturesque surroundings.
Are there any family house rentals in Chester?
In Chester, Massachusetts, there are several family-friendly house rentals available, making it a lovely spot for families to unwind. Visitors can find homes located in scenic surroundings, offering spacious living areas and fully equipped kitchens, superb for preparing family meals. Many properties feature outdoor spaces where children can play, and some may even include amenities like fire pits or barbecue grills for evening gatherings.

The town is located near attractions such as the charming Chester Theatre Company and the beautiful hiking trails of the nearby Appalachian Trail, providing plenty of opportunities for outdoor adventures. Moreover, the picturesque landscapes and small-town atmosphere contribute to a relaxing getaway for families looking to escape the hustle and bustle.
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 pet-friendly house rentals in Chester?
In Chester, Massachusetts, there are several pet-friendly house rentals available, offering a delightful retreat in a scenic, rural setting. Many of these properties are equipped with amenities such as spacious backyards, fully equipped kitchens, and cosy living areas, making them ideal for families or groups travelling with pets.

The area is surrounded by beautiful landscapes, providing ample opportunities for outdoor activities with your furry companions. Nearby, the Chester-Blandford State Forest offers numerous hiking trails and picturesque spots to explore, ensuring both you and your pets can enjoy the natural beauty of the region.
Are there any remote work holiday rentals in Chester?
In Chester, Massachusetts, there are several remote work holiday rentals available, making it an excellent choice for those looking to combine work and leisure. Many of these properties are equipped with essential amenities such as reliable Wi-Fi and dedicated workspaces, including desks, ensuring a comfortable environment for remote working. The scenic beauty of the area, with its lush forests and tranquil surroundings, provides a peaceful backdrop for productivity.

Visitors can explore local attractions such as the nearby Chester-Blandford State Forest, which offers hiking trails and opportunities for outdoor recreation. The charming town centre features quaint shops and dining options, adding to the overall experience of staying in Chester. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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.
What are popular rental amenities in Chester?
In Chester, popular holiday rental amenities include features that cater to comfort and entertainment. Many properties offer a sofa bed, which provides flexibility for accommodating extra guests. Families or groups can enjoy an arcade game room, great for leisure activities after a day of exploring the area. Additionally, rentals typically come equipped with a blender and a coffee/tea maker, allowing guests to prepare their own meals and enjoy warm beverages at their convenience. A desk is also commonly found in these properties, providing a space for work or planning activities during their stay.
When is the best time to visit Chester for a holiday rental?
The peak season to visit Chester, Massachusetts, is during the summer months of June to August, with July being the most popular month. This vibrant period attracts travellers looking to enjoy the great outdoors, with plenty of opportunities for hiking, kayaking, and exploring the charming local scenery. The warm weather, typically ranging from 15 to 30 degrees Celsius, creates a friendly space for both relaxation and adventure.

In addition to outdoor activities, summer in Chester offers a lively community spirit, with events and festivals that highlight local culture and cuisine. Visitors can soak up the sun while wandering through picturesque landscapes, making it a superb time for family trips or romantic getaways.

For those looking for more budget-friendly options, November presents an excellent alternative. The crisp autumn air, coupled with the stunning foliage, creates a picturesque backdrop for leisurely hikes and scenic drives. This quieter season allows for a more intimate experience with nature, as well as the chance to enjoy Chester's charming small-town feel without the summer crowds.

Ultimately, your choice will depend on whether you prefer the bustling energy of summer adventures or the serene beauty of the fall season.
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.
What are the top attractions in Chester?
Chester, Massachusetts, offers a charming small-town atmosphere with a variety of attractions for visitors. One of the main highlights is the picturesque Chester Village, where you can enjoy the quaint architecture and local shops. The surrounding natural beauty is enhanced by the nearby Chester-Blandford State Forest, great for hiking and exploring the scenic trails.

Additionally, the area is known for its beautiful rivers, including the Westfield River, which is popular for fishing, kayaking, and enjoying peaceful waterfront views. For those interested in local history, the Chester Railway Station, a former passenger and freight station, provides a glimpse into the town's past.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas