Chester vacation rentals

We found 95 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Chester to find one that's perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll find the amenities you need and want, which might include cable TV and a washer and dryer. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Chester

Showing deals for:Feb 20 - Feb 27

Image gallery for Welcome to the gateway of New Hampshire

Terrace/patio
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

Welcome to the gateway of New Hampshire

Windham, NH

10% off
Price is CA $397
CA $3,935 total
includes taxes & fees
Welcome to the gateway of New Hampshire

Find spaces that suit your style

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chester

Book a vacation rental for your Chester getaway

Experience the unique character of Chester with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Chester

Do you want to find attractions to visit in the area? Venture out of your cozy vacation rental and experience everything that Chester has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Chester. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Bedrock Gardens (14.3 mi / 23 km)
  • Benson Park (15.1 mi / 24.2 km)
  • Baboosic Lake Town Beach (17.2 mi / 27.7 km)

Transportation to and around Chester

Fly into Manchester-Boston Regional Airport (MHT), the closest airport, located 9.4 mi (15.1 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Nashua, NH (ASH-Nashua Municipal), which is 17.8 mi (28.6 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a vacation rental?
When considering a vacation rental in Chester, New Hampshire, the most appealing area to stay in would be close to the charming town centre. This area not only provides a picturesque backdrop with its New England architecture but also offers convenient access to local amenities. The town centre is great for leisurely strolls, where you can explore quaint shops and enjoy delightful dining options.

Another great option is the vicinity around Chester's beautiful parks, such as the Chester Town Forest. This area is ideal for outdoor enthusiasts, offering a variety of trails for hiking and nature walks, which are particularly lovely during the autumn months when the foliage puts on a spectacular display.
How much does it cost to rent a vacation home in Chester?
Prices for vacation 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 travelling 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.
Are there any discounts for Chester vacation 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 vacation rentals in Chester?
A long-stay vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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, vacation 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 vacation rental?
December is the most popular time to visit Chester, New Hampshire, as the town transforms into a winter wonderland, great for festive vacation celebrations. This charming New England locale offers a cozy atmosphere during the winter months, with opportunities for snowshoeing, cross-country skiing, and enjoying the scenic beauty of the surrounding snowy landscapes.

The peak season in Chester runs from June to August, when visitors flock to enjoy outdoor activities such as hiking and exploring the picturesque trails in the area. The warm summer weather, typically ranging from 20 to 30 degrees Celsius, creates ideal conditions for engaging in various recreational pursuits, from boating on nearby lakes to attending local fairs and festivals.

For those seeking good value, October presents a wonderful option. The fall foliage is at its peak, painting the landscape in vibrant hues of red, orange, and yellow. This quieter time allows for peaceful strolls through the autumn leaves and an opportunity to appreciate the stunning natural beauty without the summer crowds.
How early should I book a Chester vacation rental?
Book your Chester vacation 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 vacation 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 vacation 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 vacation 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.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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