Visit Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and ...
9.8/10 Exceptional! (92 reviews)
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."
Reviewed on Aug 8, 2025
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
$143 nightly
The price is $163 total per night from Aug 19 to Aug 20
$163 total
Aug 19 - Aug 20
Total includes 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 ...
8.8/10 Excellent! (1,829 reviews)
"Charming area and loved to hotel decor!"
Reviewed on Aug 11, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
$161 nightly
The price is $183 total per night from Sep 2 to Sep 3
$183 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,000 reviews)
"Beautiful hotel in a great location!"
Reviewed on Aug 10, 2025
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 Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and ...
9.8/10 Exceptional! (92 reviews)
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."
Reviewed on Aug 8, 2025
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf ...
10/10 Exceptional! (31 reviews)
"We had a great time overall! Pickleball courts and pool were the absolute highlights of the trip, with everyone getting in on the fun. The house was gorgeous with the sunroom being a bit hit every morning! Thanks!"
Reviewed on Jul 20, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
8/10 Very Good! (4 reviews)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby."
Reviewed on Jun 7, 2025
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.
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- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Sandy Point State Park
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- St. Michaels Winery
- Rock Hall Harbor
- Annapolis Harbor Center Shopping Center
- Annapolis Maritime Museum
- Maryland Quiet Waters Park
- Annapolis Mall Shopping Center
- Maryland State House
- Queenstown Premium Outlets
- Chesapeake Bay Maritime Museum
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- William Paca House
- Chesapeake Bay Environmental Center
- Annapolis Landing Marina
- Avalon Theatre
- Ego Alley
- Eastern Neck National Wildlife Refuge
- Queenstown Harbor Golf Links
- Rolphs Wharf Marina