Hotel holiday rentals in Maryland

The Cove - 9 Rooms and Conference center

Breathtaking summer, sunset view from the deck, overlooking Somers Cove Marina and the Little Annemessex River. Relax and enjoy the beauty of a small rustic town. In the heart of Crisfield MD - “The Crab Capital of the World” the Tyler family has owned and operated this property since 1980. This six bed, six bath whole house rental property is great for Family Reunions, Friends Get Together, Small Weddings, Business Meetings, etc. First floor is social area and bedrooms are on the second floor.

The Wolbert Room at the Vandiver Inn

Experience the style of a downtown boutique hotel, with the comfort of a country inn. Stay and play in a beautiful waterfront town at the award-winning Vandiver Inn, located just blocks from the Chesapeake Bay in historic Havre de Grace, Maryland. Surrounded by historic homes, museums, close to golf, shopping, antique stores, marinas and water-oriented activities, the Vandiver consists of the Historic Vandiver Mansion, the adjacent Kent & Murphy Houses, the year-round Pavilion and our Gardens.

The Avalon at the Cooper House

Gorgeous 1 bed/1 bath suite offering incredible waterfront views of the North East River. King size bed, a convertible single bed, seating and tv area, outdoor seating with unmatched water front views and private entrance. Walk to marinas, fishing, restaurants, parks, tennis, and kayak launch, excellent porch sitting, and picture perfect sunrises. The Avalon is one of three suites available at The Cooper House and can be combined to accommodate larger groups, or kept separated, if desired.

Water View with Beach, Walk to restaurants & shops

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning waterfront views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored water view rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Guest Quarters At The Inn - 205

The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and charming town of North Beach MD. The Guest Quarters are partnered with The Westlawn Inn, an award-winning fine dining restaurant with early-evening live music on the weekends. The five-unit building is in the Arts and Crafts style of the 1920s and boasts special hand-crafted detailed trim work that fits the historic charm of days gone by in the coastal town.

Iconic Bethesda Stay | Zoo. Fitness Center

Access the vibrant sights, sounds and tastes of downtown Bethesda. Perfectly located minutes from downtown D.C, Hyatt Regency Bethesda Hotel is the ideal destination for business travelers and vacationers alike. Attractions await you: ✔Bethesda Row, one-stop shop for dining, spas, shopping ✔2,000 different animals at the National Zoo ✔Amazing shows at the the Strathmore ✔Downtown Washington DC ✔Waverly Street Gallery, one of the oldest such galleries in the DC area

Cove Creek Lodge: 220 Lakeside 2-Queen w/Fireplace

Unwind & Relax in this log cabin styled spacious vaulted peak ceiling room with two Queen beds and an electric fireplace for everyone to enjoy. Equipped with a luxurious bathroom with a walk-in shower, quality bath products, Kitchenette, and Smart TV. Enjoy the fresh mountain air and your morning coffee by walking right out your door to the deck, where you have two chairs that immediately showcase a beautiful lakeview sunrise.

Walk to Bethesda Metro Station + Restaurant & Gym

Stay steps from downtown Bethesda’s buzz—local cafes, indie shops, and the Red Line Metro to D.C. all within reach. Grab a latte downstairs, hit the fitness center, or unwind in your spacious room after exploring the trails or museums. With an on-site restaurant, 24/7 market, and pet-friendly vibes, this stay blends hotel perks with the ease of Airbnb. Perfect for city hoppers, NIH visitors, or weekend adventurers.

Cozy city view room w balcony at Beach Bum Inn

Not a cookie- cutter hotel room experience- enjoy a clean, new simple room just steps away from the beach and the Boardwalk. Small indoor heated pool. Featuring private balconies facing Baltimore Ave, mini fridge, microwave and hair dryer in each guest room. Sit your beach chairs right outside your door. Light continental breakfast included for each registered guest. Kick back and relax... you're on beach time!

Wyndham National Harbor | 2BR/2BA King Bed Suite

Along the banks of the Potomac is the innovative National Harbor, a perfect springboard to experience the best of U.S. capital. This resort puts you right at the center of Maryland’s thriving waterfront district. Wyndham National Harbor | 2BR/2BA King Bed Suite • Size: 1052 - 1108 • Kitchen: Full • Baths: 2 • Accommodates: 8 Guests • Beds: Double Bed - 2 King Bed - 1 Queen Sleeper Sofa - 1

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Guests refer to Sandy Cove's 220 acres as the most peaceful, relaxing, breathtaking place on the headwaters of the Chesapeake Bay. Leave your cares behind as each night includes deluxe lodging & fun activities. Recipient of TripAdvisor's Certificate of Excellence, we offer a unique blend of Christian hospitality & amazing lodging with endless opportunity to meet your vacation needs.