Photo by Carrie-Anne Bohn

Chester holiday rentals

We found 24 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. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a TV. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Travel to charming Chester

Enjoy the history and other features of Chester. Travellers to this romantic city praise the shopping, restaurants and parks. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Chester

Are you looking for top things to see and do during your stay? Venture out of your holiday home and experience everything that makes Chester a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wild West City (10.2 mi / 16.4 km)
  • Lake Hopatcong Golf Club (11.8 mi / 18.9 km)
  • Round Valley Recreation Area (14.1 mi / 22.6 km)
  • Tomahawk Lake Water Park (14.8 mi / 23.9 km)
  • Land of Make Believe Amusement Park (16 mi / 25.8 km)
  • Florham Park Roller Rink (16 mi / 25.8 km)

Exploring the natural features in Chester

Whether you're looking for adventure or just want to take in the scenery, Chester is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Schooley's Mountain County Park (4.9 mi / 7.8 km)
  • Natirar Park (6.5 mi / 10.5 km)
  • Morristown National Historical Park (8.5 mi / 13.7 km)
  • Roxbury Township Open Space (10.5 mi / 16.9 km)
  • Morristown Green (11.3 mi / 18.1 km)
  • Lake Lackawanna (11.4 mi / 18.4 km)

How to get to and around Chester

Fly into Morristown, NJ (MMU-Morristown Municipal), the closest airport, located 14.4 mi (23.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Manville, NJ (JVI-Central Jersey Regional), which is 18.6 mi (29.9 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, New Jersey, the charming area of downtown Chester is an excellent choice. This quaint neighbourhood offers a delightful blend of historic charm and modern conveniences, making it ideal for visitors looking to experience the local culture. Here, you can enjoy a stroll along Main Street, lined with unique boutiques, cafes, and restaurants, great for sampling local cuisine.Additionally, just a stone's throw away is the picturesque Hacklebarney State Park, renowned for its stunning natural beauty and hiking trails. This park provides an excellent opportunity for outdoor enthusiasts to explore the scenic landscapes and enjoy a picnic amidst nature. The area boasts a variety of properties, suiting diverse preferences, from charming cottages to more spacious family homes.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with several options available throughout the area. These homes typically provide spacious living arrangements, featuring multiple bedrooms and fully equipped kitchens, making them suitable for families or larger groups. Many of these properties are situated in quiet, suburban neighbourhoods, offering a peaceful escape while still being conveniently located for exploring local attractions such as the charming downtown area and nearby parks.
Are there any family house rentals in Chester?
In Chester, New Jersey, there are some family-friendly house rentals available, making it a great choice for those travelling with children. The area is known for its charming suburban feel and proximity to various outdoor activities. Many of these homes feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where kids can enjoy themselves.Nearby, visitors can explore the scenic Hacklebarney State Park, which offers hiking trails and picnic spots, great for family outings. Additionally, the local community often hosts family-friendly events, adding to the welcoming atmosphere.
Are there pet-friendly house rentals in Chester?
In Chester, New Jersey, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. The area is known for its charming suburban atmosphere and proximity to beautiful outdoor spaces. Many of the holiday homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, providing guests with a home-like experience during their stay.Additionally, Chester is near several parks and nature reserves that are great for pet owners. For instance, the nearby Hacklebarney State Park offers scenic trails and picturesque settings for walks with pets, while the expansive Chester Township Park features open fields and wooded areas ideal for outdoor activities. These features enhance the appeal of the holiday rentals, allowing visitors to enjoy both the comfort of their accommodations and the beauty of nature with their pets.
Are there any remote work holiday rentals in Chester?
In Chester, New Jersey, there are several remote work-friendly 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 high-speed internet, free Wi-Fi, and dedicated workspaces, including desks and printers, ensuring a productive environment.The area is known for its picturesque charm, with attractions like the historic Chester Village and local parks offering opportunities for relaxation during breaks. Additionally, the scenic countryside and nearby hiking trails provide a lovely backdrop for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chester?
In Chester, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and fireplaces, adding a cozy touch to the accommodations. Many rentals also offer onsite parking for convenience, along with accessible parking options to cater to all guests. The presence of coffee and tea makers enhances the comfort of the stay, enabling travellers to enjoy a warm beverage at their leisure.
When is the best time to visit Chester for a holiday rental?
September is the most popular time to visit Chester, New Jersey, as the summer crowds begin to wane and the vibrant autumn foliage starts to emerge. This transition period offers a great blend of comfortable temperatures and beautiful scenery, making it an ideal time for outdoor activities and leisurely strolls through the charming downtown area.During the peak season from July to September, Chester welcomes numerous visitors who come to enjoy its picturesque parks and participate in local festivals. The weather is typically warm, with average temperatures ranging from the mid-teens to low 20s Celsius, great for sightseeing and enjoying the outdoors.For those seeking a more budget-friendly option, December presents a quieter time to explore Chester. While it's cooler, with temperatures often dipping to around 0 to 5 degrees Celsius, the holiday decorations and cosy atmosphere create a unique charm. Visitors can enjoy the local shops and festive events without the hustle and bustle of peak season.
What are the top attractions in Chester?
In Chester, New Jersey, visitors can enjoy a range of attractions that showcase the area's charm and natural beauty. The historic downtown area is filled with quaint shops and eateries, offering a delightful experience for those looking to explore local culture. The picturesque Chester Village Green is a great spot for picnics and community events, providing a lovely backdrop for relaxation.For nature enthusiasts, the nearby Hacklebarney State Park is a must-visit, featuring scenic hiking trails, tranquil streams, and opportunities for fishing. The park's lush landscapes are great for outdoor activities and enjoying a peaceful day in nature. Additionally, the historic Red Mill Museum Village, located a short drive away, offers insight into the region's history and features beautifully preserved buildings and exhibits.Chester is also close to the scenic Round Valley Recreation Area, known for its reservoir and extensive trails, ideal for hiking, biking, and fishing.
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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