Chesterfield holiday rentals

We found 127 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Chesterfield to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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Why visit Chesterfield

  • Picturesque landscapes: Experience the stunning natural beauty of Chesterfield’s lush forests and tranquil rural settings, ideal for relaxation and exploration.
  • Outdoor activities: Engage in various outdoor adventures such as hiking, biking, and bird-watching along scenic trails.
  • Historical charm: Discover the rich heritage of Chesterfield through its historical landmarks that reflect the city’s unique culture.
  • Family-friendly atmosphere: Enjoy a welcoming environment perfect for families, offering activities suitable for all ages.
  • Inviting accommodations: Relax in cosy holiday homes, charming condos, or rustic cabins surrounded by picturesque New Hampshire vistas.

Popular types of accommodation in Chesterfield

Discover Chesterfield, New Hampshire, where cosy holiday homes, charming condos, and rustic cabins await. Enjoy a lovely stay amidst local attractions and landmarks, with attentive staff ensuring a select stay experience. Perfect for travellers seeking transparency, savings and reassurance, our accommodations offer a truly inviting retreat in the heart of Chesterfield.

  • Private Holiday Homes: The top choice in Chesterfield, these residences offer the utmost privacy and comfort for a quintessential retreat.
  • Condos: Highly favoured, these modern flats provide stylish living with all essential amenities for a delightful stay.
  • Cabins: Nestled in nature, these cosy lodgings offer a rustic escape with a touch of charm.
  • Apartments: Urban and convenient, these well-appointed dwellings ensure a comfortable base for your holiday.
  • Cottages: Quaint and inviting, these traditional abodes deliver a homely atmosphere for a relaxing break.**

Top attractions near Chesterfield

Chesterfield, New Hampshire is a charming city ideal for outdoor enthusiasts, couples, and culture seekers alike. Within this delightful locale, travellers can explore lush forests, nature reserves, and farms that offer a blend of adventure and scenic beauty. Whether venturing through expansive woodlands or enjoying tranquil rural settings, visitors are sure to experience a perfect mix of nature and heritage during their stay.

  • Spofford Lake: A serene lake located 3km from Chesterfield, offering a picturesque beach, enchanting scenery and a touch of romance. A perfect spot for outdoor enthusiasts.
  • Stonewall Farm: A welcoming farm, 11km from Chesterfield, boasting the charm of friendly people and rustic countryside experiences.
  • Walpole Artisans Cooperative: An arts centre with cultural delights, situated 21km from Chesterfield, perfect for those seeking creative inspiration.

Things to do recommended for couples

Embark on a romantic journey in Chesterfield, New Hampshire, where you can explore scenic trails and cosy dining spots, perfect for a couple's retreat.

Things to do recommended for families

Families visiting Chesterfield, New Hampshire can indulge in local adventures, including scenic nature walks and interactive museums that captivate both young and old.

Things to do recommended for groups

Groups visiting Chesterfield can savour local charm, exploring historical sites and engaging in scenic countryside walks, while relishing traditional New England cuisine and lively local gatherings for an authentic experience.

*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 Chesterfield

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking pointers for you.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and much more on Stayz.
  • Traveling to Chesterfield with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Chesterfield: For many, a family holiday isn't truly complete without their four-legged companion by their side. If this resonates with you, be sure to explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Chesterfield: If you’re seeking holiday lets offering discounts for extended stays of a month or more, you’ve come to the right place. With the correct filter, you can effortlessly discover and save on monthly rentals. Consider including a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chesterfield

Chesterfield, New Hampshire offers a quaint retreat with scenic trails, historical landmarks, and a family-friendly atmosphere. Enjoy outdoor adventures and romantic settings in the heart of Cheshire County. Discover the charm of West Chesterfield and unwind amidst picturesque New Hampshire vistas, making it an ideal destination for those seeking a relaxing and adventurous holiday.

  • Brattleboro: Only 8km from Chesterfield, Brattleboro is a vibrant city where natural beauty meets thrilling adventures. Visitors here are drawn to the excellent ski opportunities, with nearby ski fields and resorts providing a perfect blend of winter sport and scenic mountain views. The area is enriched by its proximity to a picturesque lake and a majestic mountain, as well as a renowned national state park, making it an ideal destination for those seeking both excitement and tranquillity.
  • Keene: Situated 16km from Chesterfield, Keene offers an enticing mix of outdoor adventure and striking scenery. It is celebrated for its ski fields and resorts that promise an exhilarating winter experience. Beyond the slopes, travellers can explore the serene lake, appreciate the modern collegiate atmosphere of a local university, and take in the vast expanses of a national state park. Keene’s blend of natural and cultural attractions provides a well-rounded retreat for the curious visitor.
  • Spofford: A mere 6km from Chesterfield, Spofford is a charming city ideal for those seeking an outdoor, scenic, and romantic escape. With its accessible ski fields and recreational areas offering delightful winter sports experiences, Spofford charms its visitors with a serene lake, scenic mountain backdrops, and the allure of a national state park. Its inviting atmosphere and diverse natural landscapes ensure a memorable journey for all who visit.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.5°F (-5.3°C)Light RainMostly SunnySlightly LowModerately High
February24.4°F (-4.2°C)Light RainMostly CloudyAverageModerately High
March32.2°F (0.1°C)Light RainMostly SunnyAverageAverage
April44.4°F (6.9°C)Light RainMostly SunnyAverageModerately Low
May56.8°F (13.8°C)Light RainMostly SunnyAverageModerately Low
June64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
July70.7°F (21.5°C)Light RainMostly SunnySlightly HighAverage
August68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
September61.5°F (16.4°C)Light RainMostly SunnySlightly HighModerately Low
October50.0°F (10.0°C)Light RainMostly SunnyAverageAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.1°F (-1.6°C)Light RainMostly SunnySlightly LowModerately High

Booking with Stayz is simple

Are you hoping to save on your next holiday? Being flexible with your travel dates can make a significant difference, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz's Trip Board provides a dedicated space for you to plan new journeys, manage your existing arrangements, or review your bookings. The properties you've saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Head to the historical city of Chesterfield

Enjoy the history and other features of Chesterfield. This city is well-known for its shopping and restaurants. 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.

Sightseeing in and around Chesterfield

Do you want to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Chesterfield has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Winchester Speedpark (7.5 mi / 12 km)
  • Brentwood Golf Course (10.6 mi / 17 km)
  • Scott Farm Orchard (5.1 mi / 8.2 km)
  • Granite Gorge (14.2 mi / 22.9 km)
  • Honora Winery (17.1 mi / 27.6 km)
  • Pine Grove Springs Golf Course (2.4 mi / 3.8 km)

Exploring the natural features in Chesterfield

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chesterfield. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Spofford Lake (2.1 mi / 3.4 km)
  • Madame Sherri Forest (2.8 mi / 4.6 km)
  • Madame Sherris Castle Ruins (2.9 mi / 4.7 km)
  • Brattleboro Common (4.9 mi / 8 km)
  • Swanzey Lake (9 mi / 14.4 km)
  • Hogback Mountain Conservation Area (16.5 mi / 26.5 km)

Transport to and around Chesterfield

The nearest airport is in Springfield, VT (VSF-Hartness State), located 31.6 mi (50.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Manchester, NH (MHT-Manchester-Boston Regional), which is 52.3 mi (84.2 km) away.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, New Hampshire, the West Chesterfield area stands out as an excellent choice. This charming neighbourhood offers a serene environment surrounded by nature, making it great for relaxation and outdoor activities. The proximity to the beautiful Connecticut River provides opportunities for kayaking and fishing, while the nearby Monadnock State Park is ideal for hiking and enjoying stunning views of the landscape.Another appealing option is the area around Chesterfield Village, which boasts a quaint, small-town atmosphere. Visitors can explore the historical sites and take leisurely strolls through the picturesque streets. The village is also close to several local farms, where you can enjoy fresh produce and artisanal goods.There are a variety of properties available in these areas, suiting different tastes and budgets. Whether you're seeking a cosy cabin or a spacious family home, you're likely to find something that suits your needs.
When is the best time to visit Chesterfield for a holiday rental?
July is the most popular time to visit Chesterfield, as summer brings an abundance of outdoor activities and a vibrant community spirit. This peak season, which runs from July to September, attracts travellers, all eager to enjoy the stunning natural beauty of the area. With comfortable temperatures averaging between 20 to 30 degrees Celsius, visitors can partake in hiking, swimming, and exploring the lush landscapes.During this lively period, the charming town of Chesterfield offers plenty of opportunities for sightseeing, including visits to local farms and the picturesque scenery of the Monadnock region. The warm weather makes it superb for leisurely strolls through nature or picnicking by the lakes, ensuring that outdoor enthusiasts find plenty to enjoy.If you're looking for a more budget-friendly option, consider planning your visit in November. While this month may be quieter, it presents a wonderful opportunity to experience Chesterfield's serene beauty, with the stunning autumn foliage still lingering in the early part of the month. You can enjoy peaceful walks and scenic drives without the crowds, allowing for a more intimate connection to the area.Ultimately, the best time to visit Chesterfield for a holiday rental depends on your preference for either the bustling summer atmosphere filled with activities or the tranquil charm of the off-season.
What are the top attractions in Chesterfield?
In Chesterfield, New Hampshire, visitors can enjoy a serene blend of natural beauty and local charm. One of the main attractions is Lake Spofford, which offers opportunities for swimming, kayaking, and fishing, making it a popular spot during the warmer months. The surrounding area features picturesque hiking trails, providing scenic views and a chance to explore the lush forests.For those interested in history, the Chesterfield Historical Society hosts a number of events and exhibits that highlight the town's rich heritage. The nearby Monadnock State Park is also a fantastic destination for outdoor enthusiasts, offering trails that lead to the summit of Mount Monadnock, which provides breathtaking panoramic views.The quaint town centre features local shops and eateries, great for a leisurely afternoon.
Are all fees included in the Chesterfield 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 Chesterfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesterfield 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 Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield 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 Chesterfield holiday home booking on Stayz?
To find Chesterfield 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 Chesterfield?
A long-stay holiday home in Chesterfield 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 Chesterfield holiday home?
Book your Chesterfield 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 Chesterfield?
Prices for holiday homes in Chesterfield 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 Chesterfield 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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