Boutique hotel vacation rentals near Chesapeake Bay

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.

GLEN ROCK MILL INN Suite #10-King Bed

CONTINENTAL BREAKFAST INCLUDED. Each of the rooms in the historic mill, turned full service restaurant & hotel, offers old world feel, with clean modern amenities. 200 year old brick, hand-hewn beams and uneven plank floors blend with well dressed beds, tile showers, pedestal sinks and new fixtures. Dine with us, explore nearby gift & antique shops, enjoy historic tours and wineries all within a 30 minute radius. Located directly on the York County Heritage Rail Trail, we are bicycle friendly.

Starfish Room - Pool, Hot Tub, Sauna

No kids, no pets. The Starfish Room is a coastal-themed, split-level luxury bedroom with a private ensuite bathroom. The bedroom has a king-size bed and there's a seating area with comfy chairs. Enjoy the large in-ground pool, the 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!

Armistead House - Room 203 (2nd Floor)

This listing is for The Darwin Room at the historic Armistead House, which offers a total of 5 separate bedrooms. It is conveniently located within a short two block walk to the Colonial Williamsburg Historic District and its iconic Duke of Gloucester Street, museums, shopping and restaurants. It's also a short walk to The College of William & Mary and the Williamsburg Train Station. Leave your car in our free private parking lot and enjoy the short stroll to the heart of Williamsburg.

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.

The Laughing King Retreat, Cobb 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.

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.

The Garden Bedroom at Grandiflora Wine Garden

Welcome to the Garden bedroom on the second story of Grandiflora! We are a vegetarian natural wine bar and 2-bedroom inn located in the heart of Chelsea. Your spacious room overlooks the patio and vegetable garden with a view of the sunset and an intriguing view of the nearby shipyard. In your TV-free room you will have your own full bathroom (with a tub), as well as a desk for laptop work and two comfortable chairs for lounging and enjoying a glass of wine!

Classified Moto - The El Mayor Room

Since 2009, Classified Moto has been building unexpected custom bikes for people all over the world. And now, we’ve outfitted our new secret headquarters with six guest rooms that are just as fun and surprising as our bikes. Keep reading for more about Classified, but first, the EL MAYOR ROOM has caught your eye. Let’s talk about it. Named for and inspired by El Mayor Tequila, this big cozy cave is deliciously refined and thoughtfully crafted.