Hotels in Chester

Embrace coastal charm at this hotel in Grasonville, where superior rooms frame magical sunset vistas over the water. After exploring nearby walking trails, unwind in the indoor pool, hot tub, or sauna. Free breakfast fuels adventures to local restaurants.

Wake up to tranquil Chesapeake Bay vistas at this quiet waterfront retreat. Steps from the scenic bike trail with an inviting seasonal pool for afternoon dips. Complimentary breakfast fuels adventures to nearby Environmental Center and Queenstown Harbor Golf Club.

Experience coastal luxury at this modern Kent Narrows hotel with marina access. A 24-hour fitness center, bar, and café await after exploring nearby Chesapeake Bay Environmental Center. The helpful staff and convenient location make for an exceptional stay.

Overlooking the bay in Grasonville, this hotel offers a refreshing indoor pool, restaurant, and bar. Unwind on the terrace after exploring nearby Chesapeake Bay Environmental Center, with convenient room service and in-room microwaves for added comfort.

Escape to this serene Chesapeake retreat featuring an outdoor pool and indulgent spa treatments. Just minutes from Northern Chesapeake Bay and Paul Reed Smith Guitars, the hotel offers a cafe, 24-hour fitness center, and attentive staff that guests consistently praise.

Discover quiet comfort at this Grasonville hotel with complimentary buffet breakfast, WiFi, and parking. Take a refreshing swim in the seasonal outdoor pool after exploring nearby Chesapeake Bay Environmental Center. Friendly staff and clean rooms await just 50 minutes from BWI Airport.

Surrounded by garden landscapes, this waterfront B&B features in-room refrigerators and laundry amenities. After enjoying the complimentary breakfast, relax by the outdoor pool or book a massage at the spa, just minutes from Rock Hall Harbor.

Warm B&B located steps from the Naval Academy with free breakfast featuring local cuisine. Enjoy free WiFi while exploring nearby attractions like John Smith House and Annapolis City Dock. Valet parking is also available.

Nestled in the heart of Annapolis, this historic hotel offers easy access to the Naval Academy. Unwind in comfortable beds after exploring nearby attractions, or enjoy a drink at the bar. The helpful staff and clean rooms earn high praise from travelers.

Immerse yourself in Annapolis at this luxury boutique hotel near the City Dock and John Smith House. Enjoy free breakfast featuring local cuisine each morning and complimentary WiFi throughout your stay while exploring Maryland's picturesque capital.

Wake up to shimmering harbor vistas at this waterfront gem steps from U.S. Naval Academy. After breakfast at Pussers Caribbean Grille, explore nearby Ego Alley or work out in the 24-hour fitness center while luxury yachts drift by.

Experience tranquility at this Annapolis hotel with a full-service spa offering massages and facials. Swim in the indoor pool, work out at the 24-hour fitness center, and enjoy cocktails at the bar. Near Maryland Hall for Creative Arts.

This Annapolis hotel offers easy access to Navy-Marine Corps Memorial Stadium and Civil Rights Plaque. Unwind at the bar after a workout, enjoy complimentary WiFi, and start your day with free breakfast. Just a 5-minute drive from the Naval Academy.

Discover comfort at this Annapolis hotel, just 5 minutes from the U.S. Naval Academy. Start your day with a complimentary buffet breakfast before exploring nearby attractions like Navy-Marine Corps Memorial Stadium. Unwind with a drink at the bar after your adventures.

This quiet Annapolis hotel offers a peaceful atmosphere near shopping and dining options. Enjoy the 24-hour fitness center, comfortable beds, and friendly bar/lounge. Borrow free bicycles to explore nearby attractions while the helpful staff ensures a comfortable stay.

Explore downtown Annapolis from this stylish Art Deco hotel with Kitchen on West St serving regional cuisine. The 24-hour fitness center, in-room refrigerators, and microwaves enhance your stay near Annapolis Civil Rights Plaque.

Surrounded by coastal beauty, this Victorian B&B offers a refreshing outdoor pool and free breakfast in St. Michaels. Explore nearby Perry Cabin Park or hike local trails, then unwind in the garden or terrace after your adventures.

Set along Maryland's Eastern Shore, this luxurious retreat features a marina, golf course, and serene spa treatments. Enjoy cocktails at the poolside bar before savoring locally-inspired cuisine at Stars restaurant. The helpful staff ensures a peaceful waterfront getaway.