28+ Private Villas and Holiday Rentals in Chesterfield |
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Chesterfield Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesterfield

Discover more than 28 vacation rentals available in Chesterfield. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesterfield.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesterfield, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesterfield. On average, places to stay near Chesterfield offer 979.07 ft², with nightly prices averaging US $469.

With Casai, finding and comparing holiday rentals in Chesterfield is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Chesterfield

Type Count
Vacation Homes 11
Cottages 4
Holiday Apartments 1

Use these Quick Filters to Find a Holiday Rental in Chesterfield

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation 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

Top Attractions Around Chesterfield, MA

Casai offers a large selection of top attractions around Chesterfield . Research things to do on your vacation before you visit Chesterfield.


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

Other Places to Stay in Chesterfield, MA


Chesterfield Gorge 101 Properties

Frequently Asked Questions About Chesterfield?

What are the top holiday rentals in Chesterfield?

With numerous options available in Chesterfield, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesterfield:

Which holiday homes in Chesterfield are best for families?

If you're searching for a family-friendly holiday home in Chesterfield, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesterfield:

How many Casai.nz holiday rentals are available in Chesterfield?

As of 2025, Casai boasts over 28 properties listed in the Chesterfield area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesterfield.


People Also Ask

There are 28 Chesterfield, MA Holiday Rentals

Recently Booked Holiday Rentals in Chesterfield