Chester holiday rentals

We found 103 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:

  • Candia Woods Golf Links (6.8 mi / 10.9 km)
  • Liquid Planet Water Park (7.1 mi / 11.4 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:

  • Onway Lake (6 mi / 9.7 km)
  • Lake Massabesic (6.2 mi / 10 km)
  • Arlington Mill Reservoir (9.5 mi / 15.3 km)
  • Beaver Pond (11.2 mi / 18 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

What is the most popular type of holiday home accommodation in Chester?
According to our data, farmhouses are the most popular holiday home type in Chester. But of course, everyone's idea of an awesome stay isn't going to be the same. Stayz has holiday homes with every size, shape and budget in mind, and we'll help you discover your ideal match.
How much does it cost to rent a holiday home in Chester?
Length of stay, property type and time of year are some of the things that can determine the price of a holiday home. Simply enter your travel dates to find your ideal fit. From comfy cabins to plush villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Chester?
The average price for a holiday home near the beach in Chester depends on when you're travelling and the type and size of property you're searching for. You can quickly and easily find prices on Stayz by entering your destination and preferred travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in Chester?
Happily, yes. You'll have your pick of two stays that roll out the welcome mat in Chester on Stayz. Our furry best friends also deserve a little time out, so simply use our search function for pet-friendly holiday homes to find a perfect pad where your pup can join in the fun.
What are popular home amenities in Chester?
Some of the most popular home amenities people are looking for in Chester include a barbecue grill, a nearby river and an electric car charging station. Whether you're travelling with friends, family or even pets, Stayz holiday properties provide the best amenities for fun and relaxation with the people you love.
Are there holiday homes in Chester that welcome kids?
Chester has two family-friendly holiday homes. And finding a stay that welcomes kiddos is a cinch with Stayz's "Properties good for families" filter. On top of having the whole place to yourselves, you'll get access to conveniences and perks like bunk beds, yards and private pools.
What are the top attractions for families in Chester?
Keeping the kids entertained during your stay in Chester is a breeze with these top family-friendly attractions:

  • New Hampshire Aviation Historical Society
  • Liquid Planet Water Park
  • Lake Massabesic

Are there holiday homes with WiFi in Chester?
Chester has two holiday homes with WiFi, so you'll be able to stay connected during your trip. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to sending emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Chester?
Chester has two holiday homes where you can chill out in air-conditioned comfort. To locate a stay on Stayz featuring this amenity, enter your desired travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chester?
The minimum age permitted can differ across properties on Stayz, so double-check the rules of the holiday home in Chester you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Chester for?
The amount of time you can book a Chester holiday home for varies depending on the property. Just put in your dates of travel to browse options that offer extended stays. They feature all you require to make your extended trip more convenient and enjoyable, such as kitchens and air conditioning. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.