Owner Direct Vacation
Rentals in Cheshire

The Best Owner Direct Vacation Rentals in Cheshire. Explore thousands of vacation home rentals, large cabins, and villas near Cheshire

  1. Owner Direct
  2.  USA
  3.  Massachusetts
  4.  Cheshire

Explore the Best Cheshire Vacation Homes

Looking for the perfect place to stay in Cheshire? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Cheshire character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos
10 (10 Reviews)
Bed & Breakfast
Harbour House Inn B&B
  • Air Conditioner
  • Parking
  • View
US
View Availability
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9.4 (53 Reviews)
Bed & Breakfast
Harbour House Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
|
9.4 (53 Reviews)
Bed & Breakfast
Harbour House Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
10 (10 Reviews)
Bed & Breakfast
Harbour House Inn B&B
  • Air Conditioner
  • Parking
  • View
US
View Availability
10 (10 Reviews)
Bed & Breakfast
Harbour House Inn B&B
  • Air Conditioner
  • Parking
  • View
US
View Availability
|
9.4 (53 Reviews)
Bed & Breakfast
Harbour House Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
10 (10 Reviews)
Bed & Breakfast
Harbour House Inn B&B
  • Air Conditioner
  • Parking
  • View
US
View Availability
|
9.4 (53 Reviews)
Bed & Breakfast
Harbour House Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability

Why Travelers Love Using
Owner Direct to
Find Cheshire Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Popular Neighborhoods for Cheshire Vacation Rentals

What are the best areas to stay in Cheshire

Discover the top neighborhoods in Cheshire and choose a place that suits your stay.

St Mary's of the Assumption Church

St Mary's of the Assumption Church VACATION RENTALS

Sunday Feb 8

Cheshire, Massachusetts

Sun
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-20.4°C
Mon
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-15.2°C
Tue
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-8.8°C
Wed
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-5.4°C
Thu
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-8.6°C
Fri
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-11.6°C
Sat
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-10.5°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Cheshire vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Cheshire Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

Check photos, reviews, and features for your top picks.

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Cheshire Vacation Rental FAQs

1. What are the top vacation rentals in Cheshire?

There are a lot of options in Cheshire. If you plan on staying in the Cheshire area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cheshire:

2. How many vacation rentals are available in Cheshire?

Currently, the total number of properties listed in 2026 is over 7 in the Cheshire area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cheshire.