Chester holiday homes

We found 101 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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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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)
  • The Christmas Country Gallery Barn (11.6 mi / 18.7 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:

  • Onway Lake (6 mi / 9.7 km)
  • Lake Massabesic (6.2 mi / 10 km)
  • Pawtuckaway Lake (10.7 mi / 17.3 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)

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

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, great for those seeking a festive atmosphere. With the holiday season in full swing, visitors can enjoy charming decorations and local events that capture the spirit of winter. The crisp air, with temperatures ranging from -5 to 5 degrees Celsius, adds to the seasonal charm, making it a lovely time for outdoor activities such as snowshoeing or simply taking a scenic stroll through the picturesque streets.The peak tourist season in Chester runs from June to August, when families flock to the area to enjoy the warm summer weather and local attractions. This vibrant period is ideal for those looking for outdoor adventures, including hiking and swimming in nearby lakes, as well as attending community events that showcase local culture and cuisine.For those looking to travel on a budget, consider visiting in October. This month offers a quieter experience, with the stunning fall foliage providing a breathtaking backdrop for leisurely drives and hikes. The cooler temperatures and fewer crowds can make for a more intimate exploration of Chester's natural beauty.Ultimately, your choice of travel time to Chester will depend on whether you prefer the festive atmosphere of December or the lively summer months filled with activity, or if you seek the peaceful serenity of autumn.
What are the top attractions in Chester?
In Chester, New Hampshire, visitors can enjoy a range of attractions that showcase the area's natural beauty and local charm. The town is located in picturesque surroundings, with opportunities for outdoor activities such as hiking and fishing. One of the main attractions is the scenic Chester Town Forest, which features trails superb for walking or biking, allowing visitors to immerse themselves in the serene woodland environment.The historic Chester Village is also noteworthy, where you can explore quaint shops, local eateries, and the charming architecture that reflects the town's rich history. For those interested in community events, the Chester Library often hosts various programmes and activities that engage residents and visitors alike.Additionally, the nearby Derryfield Park offers recreational facilities and lovely picnic spots for families looking to enjoy a day outdoors.
Are all fees included in the Chester holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Chester holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Chester holiday homes?
You can find great discounts on holiday homes in Chester on Bookabach, 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 change or cancel my Chester holiday home booking on Bookabach?
To find Chester holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Chester holiday home?
Book your Chester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.