Hotel holiday rentals near Chesapeake Bay

All In One!

This stylish and spacious place to stay is perfect for a home away from home! Private entry! Everything you need is here! There’s a tv in the bedroom and living room. There’s a pool table if you want to play a fun game! If you need space to study or do some work, there’s a desk area. Personal washer & dryer is also available in the unit. Unit has neighbors above so you may hear noise/children occasionally during daytime hours. We do not accept inquiries with no complete profiles & no reviews.

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!

New, Luxe 2BD/1BA, <15mins to most of DC, +parking

Luxury 2BD/1BA. Perfect for traveling professionals or tourist-ing couples. High-end furnishings, full kitchen w/new appliances, washer+dryer, & office/workspace. Clean, comfortable, great light. NoMa, the best neighborhood in DC: ‣ Several bustling hubs w/ food, art, events, & shopping nearby, homes tucked between on quiet streets ‣ Transportation paradise, walk score 95%, bike score 98%, walk to 2 metros & MBT, DCA airport 15-min taxi ‣ Central location, ~15-20 minutes to see most of DC

Sea Grass Room - Pool, Hot Tub, Sauna

No kids, no pets. The Sea Grass Room is a luxury bedroom decorated in coastal style with a queen-size bed, and ensuite bathroom. Includes mini-fridge, 4k UHD smart TV, Mar Bella robes and more. 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!

“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.

The Laughing King Retreat, Parramore Island Suite

The Laughing King Retreat is an adults-only, organic waterfront farm situated directly on the peaceful waters of 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. Dig for clams, collect wild oysters, or just sit and marvel at the beauty.

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

Welcome to our charming 1BR/1BA condo close to Williamsburg! Located just minutes from historic Williamsburg, you can explore the area or stay on property and relax by the pool and enjoy the many family friendly amenities on site. Experience all that Williamsburg has to offer from historic landmarks along one of Williamsburg's many walking and biking trails like Powhatan Creek Trail, Historic Jamestown Bike Trail, and Freedom Park, historic downtown Williamsburg, and Busch Gardens.

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.

The "Cookie B", Private, Cozy and One of a Kind

The "Cookie B" is easily accessible from our adjacent parking lot via our newly lighted stairs and ramp and her position in the marina offers maximum indoor and outdoor privacy. Her bow deck is huge so catch some rays by day and star gaze by night. Then enjoy morning coffee on a covered aft deck. And the view!!!The "Cookie B" enjoys one of the most beautiful, unobstructed and unique sights to be found at any place along the James River.