48+ Vacation Rentals & Holiday Homes in Chester |
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Chester Accommodations - Hotels & Rentals

About Chester Vacation Rentals

Discover More than 48 Incredible Getaway Rentals Available in Chester. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chester.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chester, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chester. The Average Size of Places to Stay Near Chester is 1344.64 ft², with Prices Averaging US $353 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chester. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Chester

Type Count
Vacation Homes 32
Cottages 5
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Chester

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chester with Online Reservations.

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

Activities ChesterGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World ChesterGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Chester Town Hall 59 Properties

Frequently Asked Questions About Chester?

What are the top hotels, lake houses & vacation rentals in Chester?

We provide an array of great vacation destinations in Chester. If you are looking to stay in or around the Chester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chester:

Which hotel, lake house, or vacation rental in Chester is best for families?

Searching for a family-friendly getaway in Chester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chester?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 48 in the Chester area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chester.


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