Hotels Near Chester, Maryland

The little town of Chester, with its 4,000 residents, straddles Maryland's ocean gateway, Route 50, on Kent Island. Visitors to Chester can stay in the larger neighbor towns of Stevensville and Graysonville and explore the Chesapeake Bay and the Eastern Shore. You can stroll around Matapeake State Park for a view of the Chesapeake Bay Bridge or hike the nature trail at Terrapin Beach Nature Park. For a good stroll, take the Cross County Hike 3 miles east to Kent Narrows, watching the commercial and recreational boats and perhaps visiting the Chesapeake Exploration Center. Sport-fishing charters depart from area marinas. Keep your eye on the abundant waterfowl that inspire local decoy carvers to create their accurate mallard and merganser replicas.

Kent Manor Inn and Restaurant

The historic Kent Manor Inn and Restaurant, with its oldest wing dating to 1820, features 24 rooms on its 224 acres of farmland. Rooms on the first and second floors of an 1860 addition have original Italian marble fireplace mantels. Kent Manor Inn offers conference rooms, a Garden House with seating for 150 guests and a four-star restaurant in a Victorian setting offering New American cuisine with an Eastern Shore influence on the crab, duck and venison entrees. The inn hosts yoga conferences and fitness retreats. Active guests can check out free bicycles and paddle boats. Fish from the inn's pier or launch your boat. Guide dogs are the only pets accepted.  

Kent Manor Inn and Restaurant
500 Kent Manor Drive
Stevensville, MD 21666
(800) 820-4511
kentmanor.com

Hilton Garden Inn Kent Island

The Hilton Garden Inn features conference facilities, a heated indoor pool, whirlpool and fitness center and waterfront dining. All 90 guest rooms provide balconies with water views. Walk to other waterfront seafood restaurants along Kent Narrows. The adjacent Wells Cove Marina provides boat slips if you want to sail or motor right up.

Hilton Garden Inn Kent Island
3206 Main St.
Grasonville, MD 21638
(410) 827-3877
.hiltongardeninn.com

Holiday Inn Express Kent Island

Arrange a room on the water side of the property for a terrific view. The Holiday Inn Express features 76 rooms, a meeting room and an outdoor pool. You can get breakfast from 6 to 10 a.m. and walk for lunch or dinner to Annie's, the Red Eye Dock Bar, Fisherman Inn and The Narrows Restaurant. Get up early to look at waterfowl.

Holiday Inn Express Kent Island
1020 Kent Narrows Road
Grasonville, MD 21638
(410) 827-4454
hiexpress.com

Best Western Kent Narrows Inn

This 92-room hotel offers an indoor swimming pool, fitness center and hot tub. Small pets can stay for a fee. You're right on Kent Island's Cross Island Trail, so go west for the Chesapeake Bay or east to Kent Narrows.

Best Western Kent Narrows Inn
3101 Main St.
Grasonville, MD 21638
(800) 828-3361
bestwestern.com

Resources

Article Written By Jeannette Belliveau

Award-winning writer Jeannette Belliveau has written travel books and worked at the National Institutes of Health and "The Washington Post," as well as the business and sports desks of "The Baltimore Sun." She began writing professionally in 1975. Belliveau graduated summa cum laude from the University of Maryland, earning a Bachelor of Science in journalism.

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