Chester Villa Rentals

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Compare Villas, Resorts, & Rentals in Chester

60 villas and rentals
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Luxury Places to Stay in Chester

Over 51+ Luxury Places to Stay in or Near Chester
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Top-Rated Villas with a Pool in Chester

Over 1+ Top-Rated Private Villas with a Pool in or Near Chester

Pet-Friendly Villas in Chester

Over 20+ Pet-Friendly Private Villas in or Near Chester
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Large Private Villas in Chester

Over 3+ Large Villas in or Near Chester for Groups and Families
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Chester Villas, Airbnb and Holiday Homes Under $200

Over 3+ Chester Private Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Chester

Over 15+ Instantly Bookable Private Villas in or Near Chester
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Book a Last Minute Place to Stay in Chester

About Chester Vacation Rentals

There are more than 60 incredible getaway rentals that are available in Chester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chester.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chester. Places to stay near Chester are 1111.1 ft² on average, with prices averaging US $505 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Chester, CT


Chester Creek Marina 66 Properties
Chester Center 60 Properties
Norma Terris Theater 57 Properties

There are 3 hotels in Chester and 45 rentals

Recently Booked Hotels, Resorts, or Rentals in Chester

Frequently Asked Questions About Chester?

What are the top hotels or resorts 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:

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

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 60 in the Chester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chester. 

Nearby Neighborhood (2)

NeighborhoodProperty Count
Deep River Center Rental Villas and Private Getaways in Old Saybrook, Connecticut 65
Chester Center Rental Villas and Private Getaways in Old Saybrook, Connecticut 60