Cheshire Vacation Rentals

Welcome to Cheshire. Scroll down this page to find your favorite travel destination in Cheshire and browse our extensve inventory of accommodations in Cheshire. Leisure travelers planning their family vacations can get offers directly from owners of Cheshire vacation homes or houses in Cheshire. Sometimes these single rental units are referred to as Cheshire cabins or Cheshire villas. Other popular lodging options include vacation rentals in Cheshire, Cheshire apartments and condos in Cheshire. For business travelers we offer several convenient hotels in Cheshire or small boutique hotels in Cheshire area, many with the ability to book online. If you are planning a romantic getaway in Cheshire, we highy recommend our unique inventory of bed and breakfasts in Cheshire. B&Bs can also referred as small country inns in Cheshire.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at we make it easy for travelers to find best Cheshire vacation rentals using our free inquiry service or Cheshire lodging locator service. Save time searching for Cheshire rental vacations and Cheshire accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Cheshire vacation home rentals owners as well as from Cheshire resorts, Cheshire cabin rentals, and Cheshire vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Massachusetts area. Our engine will match your specific inquiry criteria with each Cheshire vacation rental listing, Cheshire vacation house or Cheshire villa in our Cheshire rental vacations inventory. Finding Cheshire vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Cheshire accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Cheshire lodging in Massachusetts.

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

  1. Inquire on ALL Vacation Rentals in Cheshire. Click "Inquire Now" (Fastest Option - Receive the most Offers)
  2. Inquire on Selected Vacation Rentals in Cheshire. Click "Check to inquire", then click "Inquire Now" (Time-Saving Option - Receive Offers from Selected Properties)
  3. Inquire only on a Specific Cheshire Vacation Rental (Take the time to review each property - Receive an offer on the Property you like)
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

ID: 323383
The Harbour House Inn Bed and Breakfast - Bed and Breakfast in Cheshire
7 Bedrooms
Sleeps 14
The harbour house inn bed and breakfast is a beautiful and historic 18th century georgian colonial. Nestled in the heart of the picturesque berkshire hills in western massachusetts, harbour house is c ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

Smart Search

*Traveling Dates:

Flexible Dates
1+ (1)
3+ (1)
6+ (1)
11+ (1)

(vacation rentals only)
4+ (1)

Lodging Types:
Bed and Breakfasts (1)

Special Features:
Children Welcome (1)
Smoking Permitted (1)
Pet friendly (1)
Handicap accesibility (1)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Williamstown (3)
Lanesboro (1)
Hancock (3)
Pittsfield (7)
North Adams (2)
Plainfield (1)
Charlemont (2)
Lenox (14)

Max Budget per Night: