Chesterfield holiday lettings

We found 93 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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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:

  • Scott Farm Orchard (5.1 mi / 8.2 km)
  • Harris Hill Ski Jump (5.3 mi / 8.5 km)
  • Brattleboro Country Club (5.7 mi / 9.2 km)
  • Brentwood Golf Course (10.6 mi / 17 km)
  • Walpole Mountain View Winery (13.7 mi / 22 km)
  • Pete's Stand Vegetables (13.1 mi / 21.1 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)
  • Chesterfield Gorge Natural Area (3.8 mi / 6.2 km)
  • Brattleboro Common (4.9 mi / 8 km)
  • Swanzey Lake (9 mi / 14.4 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 rental accommodation in Chesterfield?
The most popular types of holiday rentals in Chesterfield are houses. Ready for more choices? Vrbo 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 rental 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 Vrbo holiday rentals 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 rental. Type in your Chesterfield travel dates to view your available options on Vrbo. Can’t live without a private pool? Use our filters to select the amenities and features you want.
Are there pet-friendly holiday rentals 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 rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
What are popular rental amenities in Chesterfield?
Some of the most popular rental 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, Vrbo holiday rentals include the best amenities for making epic memories with the people closest to you.
Are there large group holiday rentals 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 rentals 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 rentals 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 rentals with air conditioning in Chesterfield?
Select your travel dates and then use the filter tool to see holiday rentals with ac in Chesterfield on Vrbo. 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 rental in Chesterfield?
The age limit can differ between properties on Vrbo, 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 rental 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 Vrbo’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.

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