60+ Vacation Rentals & Holiday Homes in Cheshire |
  1. USA
  2. Massachusetts
  3. Cheshire

Cheshire Accommodations - Hotels & Rentals

About Cheshire Vacation Rentals

Discover More than 60 Incredible Getaway Rentals Available in Cheshire. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Cheshire.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Cheshire, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Cheshire. The Average Size of Places to Stay Near Cheshire is 869.53 ft², with Prices Averaging US $342 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Cheshire. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Cheshire

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Cheshire

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Cheshire with Online Reservations.

Weather in Cheshire, MA

View the weather forecast for Cheshire before booking your Cheshire 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

Activities CheshireGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World CheshireGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


St Mary's of the Assumption Church
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Berkshire East Ski Resort
Norman Rockwell Museum
National Shrine of the Divine Mercy
Mohawk Trail State Forest
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Bridge of Flowers
Hancock Shaker Village
Pittsfield State Forest
October Mountain State Forest

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


St Mary's of the Assumption Church 54 Properties

Frequently Asked Questions About Cheshire?

What are the top hotels, lake houses & vacation rentals in Cheshire?

We provide an array of great vacation destinations in Cheshire. If you are looking to stay in or around the Cheshire area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Cheshire:

Which hotel, lake house, or vacation rental in Cheshire is best for families?

Searching for a family-friendly getaway in Cheshire? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

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

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 60 in the Cheshire area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Cheshire.


People Also Ask

Online Reservation in Cheshire

Recently Booked Hotels, Resorts, or Rentals in Cheshire