Hotels in Chester

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.

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.

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.

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.

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.

Escape to this quiet retreat with hiking trails and a garden terrace. Just minutes from Saint Michaels Village and Classic Motor Museum, this hotel offers free breakfast, WiFi and parking. Guests consistently praise the helpful staff and clean accommodations.

Positioned near Westfield Annapolis Mall, this hotel offers a peaceful retreat with an indoor pool and 24-hour fitness center. Grab meals at Annapolis Bar & Grill or unwind at the lounge while enjoying free WiFi and parking during your stay.

Wake up to a complimentary buffet breakfast at this conveniently located hotel near U.S. Naval Academy. Enjoy free WiFi and parking while exploring nearby restaurants and shops. The 24-hour fitness center keeps your routine intact during your stay.

A serene escape with 24-hour fitness center and seasonal outdoor pool near Annapolis Harbor Center. Close to shopping and restaurants with highway convenience, these suites offer free breakfast and WiFi for both business and leisure travelers.

Located just a short drive from the U.S. Naval Academy, this family-friendly hotel offers a seasonal outdoor pool and fitness center. Guests love the helpful staff and free breakfast. Annapolis Harbor Center Shopping Center is nearby for convenient retail therapy.

Just a 5-minute drive from U.S. Naval Academy, this hotel offers a 24-hour fitness center and Ports of Call restaurant. Annapolis Harbor Center and Westfield Mall are nearby, with free WiFi and parking for your convenience.

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.

Just 10 minutes from U.S. Naval Academy, this quiet hotel offers free WiFi and parking for easy exploration. After a day of nearby kayaking or hiking trails, unwind in the 24-hour fitness center. Travelers consistently praise the helpful staff and convenient location.

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.

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.