
Hotel vacation rentals near Chesapeake Bay
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Top-rated hotel rentals near Chesapeake Bay
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Deluxe King Suite in Boutique Hotel
SCH is Fredericksburg’s newest luxury boutique hotel offering the comfort of a First Class hotel with the ease of a fully automated check-in experience. Perfect for those guests needing an Extended Stay in the Fredericksburg area as every guest suite is a welcoming residential style retreat featuring a spacious living room - a separate well appointed bedroom - full kitchen equipped with Whirlpool appliances including a full size refrigerator - range - dishwasher - microwave - as well as a washer and dryer. At SCH our guests have exclusive access to our 16000 square foot Clubhouse offering complimentary daily continental breakfast and shared coworking spaces equipped with all the essentials you will need for on-the-road productivity. Our Clubhouse access includes state-of-the-art fitness center - resort style pool - game room - spa area with steam and sauna as well as a massage room. Amenity offerings can change due to the COVID19- pandemic.

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.

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!

“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.

Blue Heron Room - Pool, Hot Tub, Sauna
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!

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.

King Studio Accessible | 2500 Penn by Placemakr
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.
Popular amenities for hotel rentals near Chesapeake Bay
Family-friendly hotel rentals

Easy access to DC & just 10 mins from the airport

Suite 2C at Maison Dupont, a Dupont Circle Inn

Bridal Suite

Bayfront oasis for every season

Spanish farmhouse vibes at Arrels restaurant

Beach Quarters Resort - Ocean Front Studio

Governor's Green Resort - 2 Bedroom Deluxe

Boutique Double Room Near Colonial Williamsburg
Hotel rentals with a pool

Luxury 1 Bedroom 1 Bath Kingsmill Resort

Studio with breakfast near APG

The Homestead B&B - Sunflower Room

Wyndham Patriots Place | King Bed Studio

Fairway View King Room.

Club Wyndham Governor’s Green One-Bedroom Suite

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

*Historic Powhatan Resort- 2 Bedroom Sleeps 6
Hotel rentals with a patio

Lux 2BR PH, Private Terrace, 24/7 Onsite Team

Cozy Santorini Room at Grandiflora Wine Garden!

Armistead House - Room 203 (2nd Floor)

The Bangor D.C., Cozy Basement Apartment w/Kitchen

Renovated Hotel By Historic Park

2BR Getaway near Busch Gardens!

The Charlesworth Hotel and Restaurant on the Bay

Historic Powhatan Resort- 4 BR
Other hotel vacation rentals

Boutique Inn in the heart of scenic Deltaville, VA

Third Floor Hotel Room with Private Bath

Hotel room 1 street off beach!

Single Capsule in 18 Pod with Balcony Female only

★Historic Harrison Room -The George of Old Town★

Classic Room #7

Buttonwood Boutique Hotel - Cottage Suite A

Cozy and Independent Suite.
Quick stats about hotel rentals near Chesapeake Bay
Total rentals
160 properties
Nightly prices starting at
R173 ZAR before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
50 properties have a pool
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