48+ Vacation Home Rentals in Chester |
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Chester Vacation Rentals & Ski-in/Ski-out Homes

About Chester Vacation Rentals

Explore over 48 vacation rentals in Chester 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 Chester 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 Chester. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chester tailored to your preferences. On average, these rentals offer 1383.23 ft² of space, and are priced at an average of US $349 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Chester 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 Chester

Type Count
Vacation Homes 33
Cabin Rentals 5
Cottages 5
Holiday Apartments 2
Others 2

Use these Quick Filters to Find a Vacation Rental in Chester

★ Pro Tip: Discover Your Ideal Vacation Rental in Chester 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 Chester, MA

View the weather forecast for Chester before booking your Chester 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 Chester, MA

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


Chester Town Hall
Tanglewood Music Center
Ski Butternut
Eastern States Exposition
Big E
Holyoke Mall
Smith College
Norman Rockwell Museum
Mount Holyoke College
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Cranwell Golf Club
Jacob's Pillow
Calvin Theater
Berkshire Museum
Otis Ridge
Pittsfield State Forest
October Mountain State Forest
Blandford Ski Area

Other Places to Stay in Chester, MA


Chester Town Hall 72 Properties

Frequently Asked Questions About Chester?

What are the top vacation rentals in Chester?

When organizing your trip to Chester, 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 Chester. Peruse our collection of highly-rated properties and secure your reservation today.

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

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

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

Discover the ideal vacation rental in Chester with SunSki Resorts™. We provide an extensive selection of over 48 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Chester.


People Also Ask

There are 48 Chester, MA Vacation Rentals

Recently Booked Vacation Rentals in Chester