Chester holiday rentals

We found 97 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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Why visit Chester

  • Scenic Outdoor Spaces: Chester boasts beautiful parks and lakes, perfect for leisurely strolls and outdoor activities.
  • Family-Friendly Atmosphere: The town is ideal for families, featuring a local skatepark and various community events.
  • Charming Neighbourhoods: Visitors can explore quaint streets that reflect the town's relaxed and romantic vibe.
  • Affordability: Chester offers a range of affordable options for visitors, making it accessible for all.
  • Community Spirit: Seasonal events foster a sense of community and provide rich cultural experiences.

Popular types of accommodation in Chester

Nestled in the scenic landscapes of New Hampshire, Chester offers a charming retreat for travellers seeking tranquility and adventure. From private holiday homes to cosy cottages, the variety of holiday rentals ensures a perfect stay. Explore the natural beauty of local parks, enjoy leisurely walks through quaint streets, and immerse yourself in the community spirit at seasonal events. Discover the ideal rental location in Chester for an unforgettable getaway.

  • Private Holiday Homes: The top choice for visitors, these spacious and fully equipped residences provide a home-like atmosphere, perfect for families or groups.
  • Condos: A close second, these modern dwellings offer a blend of convenience and comfort, typically featuring shared amenities like pools and fitness centres.
  • Cottages: Quaint and charming, these cosy retreats often provide a serene escape, ideal for a peaceful getaway in nature.
  • Apartments: A practical option for solo travellers or couples, these self-contained units offer flexibility and easy access to local attractions.
  • Cabins: For those seeking rustic charm, these wooden structures nestled in the woods provide an authentic outdoor experience.**

Top attractions near Chester

Chester, New Hampshire offers a delightful mix of urban parks, lakes, and state parks perfect for outdoor, scenic, and romantic holidays. Visitors can enjoy family-friendly and cultural experiences, including the local skatepark, making it an ideal destination for an active break. The city's charm and natural beauty provide a superb backdrop for leisurely strolls and outdoor adventures, ensuring a memorable holiday in this quaint New England town.

  • Bear Brook State Park: A vast expanse of natural beauty, this park offers a perfect blend of outdoor adventure and serene landscapes. Enjoy hiking, biking, and exploring its picturesque trails and pristine waters.
  • Windham Town Beach: A delightful spot for relaxation, this beach features soft sand and calm waters, ideal for swimming, sunbathing, and picnicking with family and friends.
  • Benson Park: This urban park combines city charm with outdoor fun, featuring walking paths, playgrounds, and picnic areas, making it a perfect family-friendly destination.

Things to do recommended for couples

Discover a romantic escape in Chester, New Hampshire, where you can stroll through charming streets and enjoy intimate dining experiences. Embrace local culture, and savour every moment in this delightful town.

Things to do recommended for families

Families visiting Chester can enjoy a delightful day exploring local nature trails and engaging in interactive museum exhibits, offering a perfect blend of education and outdoor fun for all ages.

Things to do recommended for groups

Groups visiting Chester can experience the thrill of motor racing at New England Dragway, situated 19km away, and embrace the sports and adventure vibe of this local attraction.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chester

If you're travelling with a group, as a family, bringing your pets along, or seeking extended stays, be sure to filter according to your specific preferences. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Chester with a group: Think about how many bedrooms you require, along with additional features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily refine your search for all these options and more on Stayz.
  • Traveling to Chester with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Chester: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels completely at home.
  • Planning for a long term stay visiting Chester: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Chester

Chester, New Hampshire offers a delightful blend of outdoor charm and rural tranquillity. Visitors can wander through scenic streets, enjoy the relaxed family-friendly environment, and explore neighbourhoods that exude a business-friendly yet romantic atmosphere. The city's affordable prices and picturesque settings make it an ideal destination for those seeking a blend of romantic escapes and genuine New England experiences.

  • Manchester: Manchester is a bustling city situated 16km from Chester and offers a blend of family-friendly and outdoor adventure experiences. Visitors can enjoy a variety of attractions including an arena entertainment facility, educational venues and a shopping mall centre. The city’s close proximity to prominent landmarks such as a sports facility stadium, another notable stadium and a beach makes it a versatile destination for both urban exploration and leisure activities.
  • Sandown: Sandown is a charming city located 6km from Chester, ideal for those seeking outdoor, romantic and scenic experiences. The area offers a range of activities from exploring a recreational area to enjoying the thrills of an arcade adventure zone and the conveniences of a shopping mall centre. Local attractions include a serene lake, a picturesque beach and a family beach, making it a delightful escape for nature lovers and couples alike.
  • Merrimack Valley: Merrimack Valley, naturally defined by its valley landscape and situated 10km from Chester, is a haven for outdoor, scenic and romantic pursuits. The region boasts a mix of cultural and leisure activities, including educational venues, theatre performances and golf. Notable attractions such as a lake, a cape and a beach provide visitors with a diverse range of experiences, making it an ideal area for both relaxation and adventure.

Best time to go to Chester

If you're planning a trip to Chester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June, August and December, while off-peak times, like January, March and October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.0°F (-3.9°C)Light RainMostly SunnySlightly LowSlightly Low
February26.8°F (-2.9°C)Light RainMostly SunnyAverageAverage
March34.3°F (1.3°C)Light RainMostly SunnySlightly LowSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
May57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
June65.8°F (18.8°C)Light RainMostly SunnySlightly HighSlightly High
July72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
August70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
September63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnySlightly LowAverage
November40.5°F (4.7°C)Light RainMostly SunnyAverageAverage
December31.3°F (-0.4°C)Light RainMostly SunnySlightly HighAverage

Booking with Stayz is simple

Are you aiming to save on your upcoming journey? Being flexible with your travel dates can lead to significant savings, as prices tend to vary. Additionally, opting for a longer stay often results in considerable discounts. To discover the ideal Stayz property that fits your budget, make use of our filters to organise options by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's Trip Board provides a dedicated area where you can initiate new journeys, continue planning your trips, or review and organise your bookings. Properties you've bookmarked or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • Atkinson Country Golf Course (10.1 mi / 16.3 km)
  • Canobie Lake Park (11.3 mi / 18.2 km)
  • Cowabunga's (11.5 mi / 18.6 km)
  • The Christmas Country Gallery Barn (11.6 mi / 18.7 km)
  • Mel's Funway Park (12 mi / 19.3 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)
  • Exeter Recreation Park (11.5 mi / 18.6 km)
  • Windham Town Beach (12 mi / 19.3 km)
  • Bear Brook State Park (12.7 mi / 20.4 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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Chester holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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