50+ Rental Villas and Private Getaways in Chester |
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Chester Villa Rentals

About Chester Vacation Rentals

There are more than 50 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 897.27 ft² on average, with prices averaging $519 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.

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Top Private Villas, Resorts, and Rentals in Chester

Type Count
Vacation Homes 27
Cottages 3
Holiday Apartments 2
Unique Vacation Rentals 2
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Chester

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chester with BedroomVillas.

Weather in Chester, MD

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

Stay Near Chester's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Chester's Research Top Attractions For Your Vacation


Chesapeake Exploration Center
U.S. Naval Academy
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Queenstown Premium Outlets
Annapolis Maritime Museum
Chesapeake Bay Maritime Museum
Oxford Museum
Queenstown Harbor Golf Club
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club

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


Chesapeake Exploration Center 46 Properties

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:

Which hotel or resort 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?

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 2025 is over 50 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. 


People Also Ask

There are 12 hotels in Chester 1 resorts, and 30 rentals

Recently Booked Hotels, Resorts, or Rentals in Chester