Chester holiday lettings

We found 94 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 staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, such as parking and air conditioning. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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Book a holiday rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Chester

Are you hoping to find top things to see and do while you're in the area? 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:

  • Zorvino Vineyards (4.8 mi / 7.8 km)
  • Candia Vineyards (9.2 mi / 14.7 km)
  • Derryfield Golf Course (9.3 mi / 15 km)
  • Windham Country Club (10 mi / 16.2 km)
  • Atkinson Country Golf Course (10.1 mi / 16.3 km)
  • Canobie Lake Park (11.3 mi / 18.2 km)

Exploring the natural landscape of Chester

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chester. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Lake Massabesic (7.4 mi / 12 km)
  • Windham Town Beach (12 mi / 19.3 km)
  • Bear Brook State Park (12.7 mi / 20.4 km)
  • Benson Park (15.1 mi / 24.2 km)
  • Baboosic Lake Town Beach (17.2 mi / 27.7 km)
  • Mine Falls Park (18.8 mi / 30.3 km)

Transport to and around Chester

Fly into Manchester, NH (MHT-Manchester-Boston Regional), the closest airport, located 9.4 mi (15.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Nashua, NH (ASH-Nashua Municipal), which is 17.8 mi (28.6 km) away.

Frequently asked questions

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.
What are popular rental amenities in Chester?
In Chester, New Hampshire, holiday rentals tend to focus on providing a comfortable home-like experience, although there are no specific popular rental amenities noted. Visitors can generally expect basic conveniences such as kitchens for self-catering, living areas for relaxation, and outdoor spaces where guests can enjoy the natural surroundings. Some properties might also feature amenities like fireplaces for a cosy atmosphere during colder months.
When is the best time to visit Chester for a holiday rental?
December is the most popular time to visit Chester, New Hampshire, as the town transforms into a winter wonderland, attracting travellers eager to embrace the festive spirit. During this month, visitors can enjoy various holiday activities, including local festivals and charming winter markets, all set against the picturesque New England landscape.

The peak season in Chester runs from June through August, when warm temperatures and longer days entice outdoor enthusiasts to explore the area's parks and trails. This vibrant period is great for families seeking adventure, as it offers a wealth of recreational opportunities like hiking, cycling, and picnicking in the sun-drenched parks.

For those looking for a quieter experience, October presents a wonderful opportunity to witness the breathtaking fall foliage that New England is famous for. The weather is typically mild, with temperatures ranging from 10 to 15 degrees Celsius, making it ideal for scenic drives and leisurely strolls through colourful landscapes. This month not only allows for a peaceful retreat but also often comes with more affordable rental options.
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 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.

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