Hotels in Hillsmere Shores

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.

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.

Soak in the charm of this waterfront getaway near Higgins Yacht Yard and Marina. Enjoy complimentary breakfast before exploring Muskrat Park. After sightseeing, unwind with drinks at the bar or grab a bite at the on-site café.

Immerse yourself in small-town charm at this cozy B&B featuring a lovely garden and terrace. Enjoy complimentary full breakfast daily before exploring nearby hiking trails or Perry Cabin Park. Free WiFi and parking complete your Eastern Shore retreat.

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.

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.

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.

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.

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.

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.

Set on the bay, this Tilghman hotel offers waterfront relaxation with complimentary breakfast and free parking. Explore by kayak or bicycle with onsite rentals, or unwind at the marina. Each room includes convenient refrigerators and microwaves for added comfort.

This waterfront inn on Tilghman Island features a seasonal outdoor pool and welcoming restaurant with bar. Near local marinas, it offers free breakfast, WiFi, and parking. Guests can relax on the terrace or stroll through the garden while experiencing exceptional staff service.

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.

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.

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.

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.