Chester, MD
Travel Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
$133 nightly
The price is $151 total per night from Jul 7 to Jul 8
$151 total
Jul 7 - Jul 8
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! (1,856 reviews)
"Maryland Inn is an absolutely fantastic location, but that’s about the only positive I have for it. There’s quite a stench to the place from the time you walk in the front door. We had room 1301. It looks very nice in pictures, but it has the same odor as in the hallways, and the floor was insane ..."
Reviewed on Jun 19, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night from Jul 5 to Jul 6
$127 total
Jul 5 - Jul 6
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 ...
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$246 nightly
The price is $280 total per night from Jul 1 to Jul 2
$280 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (938 reviews)
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. ..."
Reviewed on Jun 17, 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.
Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.
Annapolis MD
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Annapolis City Dock and Sandy Point State Park are located ...
10/10 Exceptional! (110 reviews)
"We had a wonderful three-night stay and couldn’t have been more pleased with both the property and the host. The cottage was exceptionally comfortable, relaxing, spotless, and very dog-friendly. It provided the perfect place to unwind while visiting family.We did experience a power outage during ..."
Reviewed on Jun 14, 2026
Grace Cottage, St Michaels Walk to everything!
Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (6 reviews)
"We had such a wonderful time staying at Grace Cottage. Lisa, the hostes, was very responsive and very, very kind. The cottage was right in the middle of all shopping and restaurants. It is beautifully decorated and is totally stocked with everything you would need. Thank you so much Lisa for making ..."
Reviewed on May 8, 2026
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! (59 reviews)
"Beautiful home on the water! Everything was very clean and Julia was amazing! She answered my questions instantly and made the whole experience easy. We walked to the local spot on the water and had a great time hanging out with the locals, great food and water views. Julia offered a ton of options ..."
Reviewed on Jun 19, 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
Explore a world of travel with Expedia
- Stevensville Hotels
- Hotel Wedding Venues Hotels in Stevensville
- Marriott Hotels & Resorts in Stevensville
- Extended Stay America Hotels in Stevensville
- Romantic Hotels in Stevensville
- 5 Star Hotels in Stevensville
- Houseboats in Stevensville
- 3 Star Hotels in Stevensville
- Extended Stay Hotels in Stevensville
- Apartments in Stevensville
- Best Western Hotels in Stevensville
- Historic Hotels in Stevensville
- B&B in Stevensville
- Hotels & Resorts for Couples in Stevensville
- Villas in Stevensville
- Condo Rentals in Stevensville
- Hotels with a Pool in Stevensville
- Beach Hotels in Stevensville
- 4 Star Hotels in Stevensville
- Resorts & Hotels with Spas in Stevensville
- Motels in Stevensville
- Family Hotels in Stevensville
- Vacation Homes in Stevensville
- Hotels with an Outdoor Pool in Stevensville
- Hotels with Free Parking in Stevensville
- Kent Narrows Hotels
- Oceanfront Hotels in Kent Narrows
- 3 Star Hotels in Kent Narrows
- Kent Island Hotels
- Best Western Hotels in Kent Island
- Luxury Hotels in Kent Island
- Hotels & Resorts for Couples in Kent Island
- Red Roof Inn Hotels in Kent Island
- Hotels with Restaurants in Kent Island
- Motels in Kent Island
- Houseboats in Kent Island
- Vacation Homes in Kent Island
- Condo Rentals in Kent Island
- Hotels with Room Service in Kent Island
- Golf Hotels in Kent Island
- Hotels near Chesapeake Bay Environmental Center
- Northern Chesapeake Bay Hotels
- Marriott Hotels & Resorts Hotels
- Hostels in Northern Chesapeake Bay
- Resorts in Northern Chesapeake Bay
- 5 stars
- Condo Rentals in Northern Chesapeake Bay
- Houseboats in Northern Chesapeake Bay
- Grasonville Hotels
- Cheap Hotels in Grasonville
- Hotels with Hot Tubs in Grasonville
- B&B in Grasonville
- Hotels & Resorts for Couples in Grasonville
- Hotels with Balconies in Grasonville
- Oceanfront Hotels in Grasonville
- Hotels with an Outdoor Pool in Grasonville
- Beach Hotels in Grasonville
- Hotels with an Indoor Pool in Grasonville
- Resorts & Hotels with Spas in Grasonville
- 5 Star Hotels in Grasonville
- Hotels with Connecting Rooms in Grasonville
- Hotel Wedding Venues Hotels in Grasonville
- Hotels with Restaurants in Grasonville
- Vacation Homes in Grasonville
- Motels in Grasonville
- Romantic Hotels in Grasonville
- Luxury Hotels in Grasonville
- Houseboats in Grasonville
- 3 Star Hotels in Grasonville
- Hotels near Eastern Neck National Wildlife Refuge
- Hotels near Chesapeake Bay Bridge
- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- Maryland State House
- Navy-Marine Corps Memorial Stadium
- Queenstown Harbor Golf
- Northern Chesapeake Bay
- Annapolis Harbor Center Shopping Center
- Annapolis Mall Shopping Center
- Rock Hall Harbor
- Queenstown Premium Outlets
- Maryland Quiet Waters Park
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- Chesapeake Bay Environmental Center
- St. Michaels Winery
- Thanksgiving Farm Wines
- Annapolis Maritime Museum
- Annapolis Landing Marina
