105+ Vacation Home Rentals in Cheshire |
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  3. New Haven
  4. Cheshire

Cheshire Vacation Rentals & Ski-in/Ski-out Homes

About Cheshire Vacation Rentals

Explore over 105 vacation rentals in Cheshire with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Cheshire for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Cheshire. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Cheshire tailored to your preferences. On average, these rentals offer 595.17 ft² of space, and are priced at an average of US $276 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Cheshire at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Cheshire

Type Count
Vacation Homes 46
Holiday Apartments 45
Cottages 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Cheshire

★ Pro Tip: Discover Your Ideal Vacation Rental in Cheshire with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Cheshire, CT

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

Top Attractions Around Cheshire, CT

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


Cheshire Golf Course
Quinnipiac Recreation Area
Cheshire Hollow Farm
Roaring Brook Park
Barker Museum
Drazen Orchards
Maplecroft Plaza Shopping Center
Bartlem Park
Yale University
XL Center
Yale-New Haven Hospital
Xfinity Theatre
University of Hartford
Toyota Presents Oakdale Theatre
Connecticut Convention Center
Quinnipiac University
Trinity College
Wesleyan University
Shubert Theater
Palace Theatre

Other Places to Stay in Cheshire, CT


Quinnipiac Recreation Area 143 Properties
Cheshire Golf Course 134 Properties
Barker Museum 114 Properties
Maplecroft Plaza Shopping Center 101 Properties
Cheshire Historic District 98 Properties
Drazen Orchards 93 Properties
Bartlem Park 90 Properties
Roaring Brook Park 90 Properties
Cheshire Hollow Farm 26 Properties

Frequently Asked Questions About Cheshire?

What are the top vacation rentals in Cheshire?

When organizing your trip to Cheshire, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Cheshire. Peruse our collection of highly-rated properties and secure your reservation today.

Which vacation homes or resorts in Cheshire are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Cheshire. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Cheshire?

Discover the ideal vacation rental in Cheshire with SunSki Resorts™. We provide an extensive selection of over 105 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Cheshire.

Nearby Neighborhood (1) 
Neighborhood Property Count
Milldale Vacation Rentals in New Haven, Connecticut 38

People Also Ask

There are 105 Cheshire, CT Vacation Rentals

Recently Booked Vacation Rentals in Cheshire