Chesterfield holiday rentals

We found 123 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:

  • Brattleboro Country Club (5.7 mi / 9.2 km)
  • Brentwood Golf Course (10.6 mi / 17 km)
  • Granite Gorge (14.2 mi / 22.9 km)
  • Scott Farm Orchard (5.1 mi / 8.2 km)
  • Harris Hill Ski Jump (5.3 mi / 8.5 km)
  • Hidden Springs Maple (7.3 mi / 11.8 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)
  • Bear Mountain State Forest (3.5 mi / 5.6 km)
  • Chesterfield Gorge Natural Area (3.8 mi / 6.2 km)
  • Wantastiquet Mountain (3.8 mi / 6.2 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 most popular type of holiday home accommodation in Chesterfield?
The most popular types of holiday homes in Chesterfield are houses. Ready for more choices? Stayz has plenty of options to match our guests' requirements, so you'll see holiday homes in all sizes and shapes. The perfect home away from home is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Chesterfield?
Property type, length of stay and season are some things that can determine the price of a holiday home. Simply enter your travel dates to find your perfect fit. From cosy chalets to sprawling luxury villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Chesterfield?
When you travel and the style and size of the property will determine the cost of your beachside holiday home. Type in your Chesterfield travel dates to view your available options on Stayz. Can't live without a private pool? Use our filters to select the amenities and features you want.
Are there pet-friendly holiday homes in Chesterfield?
Pack a travel bag for your pup because Chesterfield has seven stays that put out the welcome mat to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
What are popular home amenities in Chesterfield?
Some of the most popular home amenities people look for in Chesterfield include a lake view, a garden and a barbecue grill. Whether you're travelling with buddies, family or even pets, Stayz holiday homes include the best amenities for making epic memories with the people closest to you.
Are there large group holiday homes in Chesterfield?
With six Chesterfield properties that can host five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal gathering or a special event, we'll help you book a comfortable space to fit the occasion.
Are there holiday homes in Chesterfield that welcome kids?
Chesterfield has seven family-friendly holiday homes. And tracking down a stay that welcomes kids is a cinch with our "Properties good for families" filter. Besides having the entire place to yourselves, you'll also enjoy access to amenities and perks such as bunk beds, full kitchens and private pools.
What are the top attractions for families in Chesterfield?
There are lots of cool things to see and do with the family in Chesterfield, such as:

  • Spofford Lake
  • Stonewall Farm
  • Wantastiquet Mountain

Can I find two-bedroom holiday homes in Chesterfield?
Take your pick of two two-bedroom properties in Chesterfield. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's lucky enough to be coming along for the ride.
How can I find holiday homes with air conditioning in Chesterfield?
Select your travel dates and then use the filter tool to see holiday homes with ac in Chesterfield on Stayz. With five air-conditioned properties on offer here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Chesterfield?
The age limit can differ between properties on Stayz, so check the rules of the holiday home in Chesterfield you're considering. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Chesterfield for?
It really depends on the Chesterfield property. To see all available options offering extended stays, simply enter your dates and number of people into Stayz's search page. You can look forward to having the property to yourself, along with home comforts like a kitchen, air conditioning and a yard where the kids can burn off energy. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.