Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Holiday Rentals in Chesterfield

Interior
Walk to Trails: Artsy Mtn-view Getaway in Vernon!

Walk to Trails: Artsy Mtn-view Getaway in Vernon!

3.0 star property
Vernon
10.0 out of 10, Exceptional, (1)
"Nice place out of the way but not too far from main roads, quiet and cozy"
United States
Julian
Walk to Trails: Artsy Mtn-view Getaway in Vernon!
Interior
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
Royalston
10.0 out of 10, Exceptional, (2)
"Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors."
United States
Melissa
Historic Home w/ Modern Updates on < 4 Acres
Interior
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Wilmington
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Interior
Quaint Massachusetts Home w/ Yard & Grill!

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Gill
Quaint Massachusetts Home w/ Yard & Grill!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"Very professional people good service good staff "
George 1-night trip
Posted 5 days ago
Days Inn by Wyndham Keene NH

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its shopping and restaurants.

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like Spofford Lake. While here, Asbury United Methodist Church and Pisgah State Park are other places worth a visit.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for families.