48+ Rental Villas and Private Getaways in Chester |
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Chester Vacation Rentals & One Degree Stays Homes

About Chester Vacation Rentals

There are more than 48 vacation rentals that are available in Chester. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Chester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Chester. Places to stay near Chester are 1282.41 ftยฒ on average, with prices averaging $318 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Chester

Type Count
Vacation Homes 31
Cottages 6
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Chester

โ˜… Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.

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 60ยฐF       Low 26ยฐF
March - May
High 77ยฐF       Low 40ยฐF
June - August
High 91ยฐF       Low 64ยฐF
September - November
High 84ยฐF       Low 38ยฐF

Top Attractions Around Chester, MA

OneDegreeStays 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 59 Properties

Frequently Asked Questions About Chester?

What are the top vacation rentals in Chester?

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

Which vacation homes in Chester are best for families?

If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:

How many onedegreestays vacation rentals are available in Chester?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 48 in the Chester area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Chester.โ€ฏ


People Also Ask

There are 48 Chester, MA Vacation Rentals

Recently Booked Vacation Rentals in Chester