Chester, MD

Travel Guide

A boat docked at a pier during twilight with a city skyline in the background.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$83 nightly
The price is $95 total per night from Sep 27 to Sep 28
$95 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$147 nightly
The price is $168 total per night from Sep 27 to Sep 28
$168 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Sep 27 to Sep 28
$125 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,005 reviews)
"Very nice property, toilet needs upgrade."

Reviewed on Sep 19, 2026

Crowne Plaza Annapolis by IHG
See all 1,214 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Crab Alley | Waterfront Home + Hot Tub + Game Room

Crab Alley | Waterfront Home + Hot Tub + Game Room

Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (4 reviews)
"Overall property was great and as listed. Views onto the water was awesome, but getting in and out of the water would have been difficult if we wanted to, as we didn’t see a functioning ladder."

Reviewed on Aug 20, 2026

Crab Alley | Waterfront Home + Hot Tub + Game Room
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."

Reviewed on Aug 3, 2026

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"

Reviewed on Aug 24, 2026

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
See all properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
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Things to do

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

$159
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

$270
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
See all activities in Chester

Frequently asked questions

When is the best time to visit Chester?
The best time to visit Chester is from May through September, when the climate is generally most pleasant for exploring. For fewer crowds and better value, the quieter months of November through February offer a cooler experience and fewer travelers.
What cuisines can you find in Chester?
In Chester you can find Mexican cuisine, with popular dishes like tacos, burritos, and enchiladas. Travelers also have options for Italian, North American (including Southern soul food and New American), and Asian (such as Chinese, Japanese, and Thai) dishes. You can also find Latin American and Mediterranean choices.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chester

A large suspension bridge spanning a wide river with a clear sky above.

Grasonville

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

Stevensville

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