Chester, MD
Travel Guide
Visit Chester
Waterfront Sunset Bayview: sleeps 6
Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (26 reviews)
We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ...
Reviewed on Apr 21, 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ...
10/10 Exceptional! (126 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on Sep 14, 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
$167 nightly
The price is $190 total per night from May 31 to Jun 1
$190 total
May 31 - Jun 1
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 ...
9/10 Wonderful! (1,846 reviews)
Awesome as usual
Reviewed on May 6, 2026
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.
Waterfront Sunset Bayview: sleeps 6
Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (26 reviews)
We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ...
Reviewed on Apr 21, 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ...
10/10 Exceptional! (126 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on Sep 14, 2025
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
10/10 Exceptional! (53 reviews)
Absolutely Lovely, Julia was very sweet and the home had everything you could have thought of or forgotten to bring.
Reviewed on Apr 13, 2026
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.
Popular places to visit
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.
Things to do
2 Hour Chesapeake Day Sail on Catamaran Epiphany
$245
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
$160
per adult
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- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay
- Chesapeake Bay Bridge
- Annapolis City Dock
- Sandy Point State Park
- Annapolis Mall Shopping Center
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- Navy-Marine Corps Memorial Stadium
- Northern Chesapeake Bay
- Maryland State House
- Chesapeake Bay Maritime Museum
- Annapolis Harbor Center Shopping Center
- Maryland Quiet Waters Park
- St. Michaels Winery
- William Paca House
- Annapolis Maritime Museum
- Queenstown Harbor Golf
- Rock Hall Harbor
- Queenstown Premium Outlets
- Avalon Theatre
- Chesapeake Bay Environmental Center
- Annapolis Landing Marina
- Maryland Hall for Creative Arts
- Fort Smallwood Park
- Ego Alley
