28+ Hotel & Resort Deals in Chesterfield |
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Chesterfield Hotels, Resorts, and Rentals

About Chesterfield Vacation Rentals

There are more than 28 places to stay in Chesterfield that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chesterfield.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chesterfield, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chesterfield. Places to stay near Chesterfield are 979.07 ft² on average, with prices averaging ZA R8,085 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chesterfield with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chesterfield

Type Count
Vacation Homes 11
Cabin Rentals 8
Cottages 4
Others 4
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Chesterfield

★ Pro Tip: Hotala.co.za has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chesterfield.

Weather in Chesterfield, MA

View the weather forecast for Chesterfield before booking your Chesterfield Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Chesterfield's Top Attractions

Hotala.co.za can help you find hotels, resorts, and rentals near many of Chesterfield's top attractions, neighborhoods, and points of interest.


Chesterfield Gorge
University of Massachusetts-Amherst
Amherst College
Big E
Berkshire East Ski Resort
Holyoke Mall
Smith College
Mount Holyoke College
Mohawk Trail State Forest
Lee Prime Outlets
Deerfield Academy
Greenfield Community College
Jacob's Pillow
Calvin Theater
Berkshire Museum
Bridge of Flowers
Magic Wings Butterfly Conservatory
Otis Ridge
October Mountain State Forest
Blandford Ski Area

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Chesterfield Gorge 101 Properties

Frequently Asked Questions About Chesterfield?

What are the top hotels or resorts in Chesterfield?

You have a lot of choices in or near Chesterfield. If you need a hotel in the Chesterfield area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chesterfield:

How many hotels, resorts, or rentals are available in Chesterfield?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 28 in the Chesterfield area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chesterfield.


People Also Ask

Hotels in Chesterfield and 20 rentals

Recently Booked Hotels, Resorts, or Rentals in Chesterfield