Hotel holiday rentals near Chesapeake Bay

The Laughing King Retreat, Honeymoon Island Suite

The Laughing King Retreat is an adults only, organic waterfront farm situated directly on the peaceful waters of the Chesapeake Bay. Your private guest suite will enjoy breathtaking sunrises and sunsets, private waterfront pool, private beach, hiking trails, miles of soft sugar sand sandbars to explore and enjoy. Private Chesapeake Bay water access for boating, swimming, paddle boarding, fishing or just soaking. For a complete list of all the retreat rooms click the photo of me and Suzanne.

Palm Tree Room - Pool, Hot Tub, Sauna

No kids, no pets. The Palm Tree Room is a spacious luxury bedroom in british colonial style with an ensuite bathroom. The bedroom has a king size bed and seating area with comfy chairs and a desk. Enjoy the large in-ground pool, huge jetted spa/hot tub and Himalayan salt sauna. 10 minutes to the Rehoboth Beach boardwalk, just minutes from a wide array of great dining and 130 outlet stores, a short hop to Cape Henlopen State Park, Lewes, Dewey beach and much more. It's time to hit the beach!

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!

“Pretty In Pink” at the Terry House !

This stylish and unique place sets the stage for a memorable trip. We purchased The Terry House, in January of 2023 and have been renovating the home for the last two years. This room is on the 2nd floor inspired by Jackie Kennedy featuring antique and historic art work. This private room is spacious, with a queen bed as well as private baths and a mini fridge in the room. There is a common area space called the parlor room on the first floor with a Keurig and microwave for you to use.

Kingsmill Resort Hotel room with 2 queen beds

Hotel room with queen bed and queen sofa bed on the 9th green of the river course. No smoking unit and property . Walkable to the convention center, fitness center and pools . Only 3 mile drive to William and Mary College and next door to Bush Gardens . The mill is a short walk for coffee and sandwiches. . The Kingsmill resort pools, courses, the resort Health Club, Lazy River, and the full-service restaurants are restricted to Kingsmill Members only. Inquire access from host

Maurice Inn and Fusion Bistrot Yellow Room

Beautiful Boutique Inn in beautiful Onancock. Close to everything with a fine dining fusion restaurant on premises offering fresh local produce prepared with international flair. Nearby is Onancock Wharf where you can kayak, paddle board or take a trip to unique Tangier Island in the middle of The Chesapeake Bay. A short drive away is international tourist destination Assateague National Wildlife Refuge with its beautiful beach and wild ponies. Come unwind for a day or a week!!

“Out to Sea” at the Terry House !

The Terry House, a Federal Townhouse circa 1860, is located in historic New Castle, Delaware. This room is on the 2nd floor, featuring a historical nautical theme in one room and historical classic cars in the other room. This suite features, a queen and a full beds as well as private baths and a mini fridge in each room. There is a common area space called the parlor room on the first floor to work, hangout, or play games. ** Not serving breakfast at the moment.

Spanish farmhouse vibes at Arrels restaurant

The hotel may require a credit card or deposit for incidentals. Resort fee of USD 40.58 per night, per room is collected by the hotel. Immerse yourself in the energy of the city with our City View King room. This room features a comfortable king-sized bed and offers captivating views of Washington, DC, providing a stylish and relaxing space for your stay. Enjoy the essence of the city from the comfort of your room in our City View King accommodation.

2 Queen Apt Suite | 2500 Penn Placemakr Experience

Once an established hotel, this building has been reimagined as residential apartment living. These are hospitality-infused homes, with amenities such as complimentary wi-fi & cable, a la carte cleaning services, and on-site support all at your disposal. You'll get a professionally managed, dynamic space, in an interesting neighborhood that feels part-residential, part-hotel - the best of both. You've never lived in a space like this.

Walk to U.S. Capitol | Rooftop Bar. Gym + Dining

Stay steps from the U.S. Capitol and Navy Yard at AC Hotel Washington DC Capitol Hill. Enjoy rooftop views at Smoke & Mirrors Bar, modern rooms with Smart HDTVs and free Wi-Fi, and European-inspired breakfast at AC Kitchen. Walk to Nationals Park or explore nearby Smithsonian museums via Metro. On-site perks include a fitness center, 2 restaurants, curated retail, hydration stations, and sleek guest rooms designed for productivity.

Deluxe Studio Apt | Dupont Circle | Placemakr

Welcome to Placemakr Dupont Circle, a beautifully restored 1903 mansion that blends history with sophistication. It’s the perfect retreat, featuring queen beds, modern kitchenettes, and stylish bathrooms. Consider it an ideal home base after exploring Washington, D.C.’s many highlights — from boutique shops and galleries to countless museums and iconic landmarks like the White House, National Mall, and other must-see sights.