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Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chesterfield holiday rentals

Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,017 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is S$219
includes taxes & fees
10 Aug - 11 Aug
Berkshire Mountain Lodge
Front of property

Steps to Holyoke Medical Center! Remote-work Hub

Steps to Holyoke Medical Center! Remote-work Hub
3.0 star property
Holyoke
The price is S$684
includes taxes & fees
26 Jul - 27 Jul
Steps to Holyoke Medical Center! Remote-work Hub
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

The Ellery

The Ellery

10/10 Excellent
"Very cozy bed in a large, airconditioned room and super convenient location. Would definitely stay here again -- the staff are lovely!"
Lisa 1-night trip
Posted 4 hours ago
The Ellery

Frequently asked questions

Can I find holiday rentals 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 restaurants and shopping. Make sure you have time to check out the parks while you're in the area.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Chesterfield Town Hall are other places to visit while you're in town.

What’s a holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family getaway.