Boutique hotel vacation rentals in Delmarva Peninsula

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.

Charming bedroom in historic Chalfonte Hotel

Private Bedroom in the Historic Chalfonte Hotel. This third floor room sleeps two people max in a full sized bed. The bathroom is shared on the hall; there are 2 bathrooms shared by 4 rooms. Free on street parking surrounds the hotel and you will enjoy easy access to the beach, popular shops and restaurants from our location in the heart of the historic district. The Chalfonte offers the Magnolia Room Restaurant and King Edward Bar onsite, featuring southern style cuisine and live music.

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.

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!

Barksdale Suite - Strawberry Hill Petersburg

Stay a short walk away from Petersburg's urban amenities in Strawberry Hill, a one-of-a-kind, lovingly restored home built in 1792. Once you arrive you will feel like you stepped into the 18th century. Named for Strawberry Hill’s first owner and inhabitant, the Barksdale suite impresses in black and gold splendor. Complete with a king bed, attached sitting room, and private bathroom, this room is Strawberry Hill’s most accessible room, just steps from the front door on the first floor.

“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.

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!!

Buttonwood Boutique Hotel - Cottage Suite A

The Buttonwood Boutique Hotel is a wonderful destination for visitors to Cape May! Its convenient location with a short 10 minute walk to the beaches, restaurants, & shopping, coupled with the historic charm & private suites, make it an enticing choice for travelers seeking a memorable experience. The communal spaces provide opportunities for guests to relax & socialize, enhancing the overall atmosphere of hospitality and warmth. You will feel right at home during your stay!

“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.