Boutique 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.

Luxury 1 Bedroom 1 Bath Kingsmill Resort

Welcome to your serene stay in the heart of Kingsmill, a private, gated community nestled along the James River. This one-bedroom guest room offers a peaceful escape. Please note, this listing does not include a kitchen or living room. Inside, you'll find a luxury king-size mattress for the ultimate night’s sleep, a remodeled bathroom with a spacious walk-in shower, HD TV and cable for unwinding after a day out, and your own private porch with Adirondack chairs overlooking the ninth fairway.

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.

Blue Heron Room - Pool, Hot Tub, Sauna, Spa

No kids, no pets. The Blue Heron Room is a spacious luxury bedroom with a vaulted ceiling, king-size bed, private ensuite bathroom and private garden patio. Enjoy the large in-ground pool, the huge jetted spa/hot tub and Himalayan salt sauna, hammocks, fire pits and more. 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!

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!!

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 Hotel at Classified Moto - Schnickschnack Room

We’re stoked you’ve discovered The El Mayor Room at Classified Moto! Our new custom designed hotel near downtown Richmond has five artfully crafted guest rooms to choose from and an array of great common areas to relax and work. If you love a good vibe and want something beyond the typical chain hotel experience, you’re in luck. Some like bright and breezy — some prefer moody and vibe-y. If you’re the latter, The Schnickschnack Room is your huckleberry.

Sandaway Suites & Beach Boutique Hotel, Water View

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

The Tydings Room at the Vandiver Inn

Premium Room | Second Floor, Vandiver Mansion The Tydings Room is a spacious retreat featuring calming sage and white décor, an elegant four-poster king bed, French poster art, a beautiful white brick mantel with a clean-burning eco-fireplace, a mini refrigerator, and a charming vintage pink bathroom with a tub/shower. Connect to the adjoining Fair Room through a private hallway to create a spacious two-bedroom, two-bath Grand Suite.

★Historic Harrison Room -The George of Old Town★

The William Harrison room is a great place to call home while you're visiting Old Town. On the third floor of the George, this room can accommodate up to 2 guests with its lush velvet headboard on king bed with small balcony and exterior circular staircase. The en suite bathroom has a large walk-in shower and white subway tile and plush towels. Views of the back patio area and surrounding buildings.

The Hearth Room - Strawberry Hill Petersburg

Walled by the original granite foundation dating to 1792, The Hearth Room is Strawberry Hill’s cozy and inviting basement room. Accessible by a private entrance on the west side of the building, this is the only pet-friendly room at Strawberry Hill. Featuring a full-sized brass bed, a 50” smart TV, and antique furnishings, your stay promises to be comfy and memorable.

Pinewood 102 Inn at Old Beach

A luxurious stay awaits you at The Inn at Old Beach. A renovated personalized Inn that is just steps away the ocean. Complimentary breakfast is served weekend mornings. Parking is first come first served, limited and not guaranteed. You may only park one vehicle at the Inn per reservation. Please contact us if further accommodations are needed.