Hotel vacation rentals near Chesapeake Bay

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Top-rated hotel rentals near Chesapeake Bay

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A well-appointed bedroom features a spacious bed with a blue accent pillow. Light blue wall designs create a soothing atmosphere, while a large mirror reflects the bed. Nightstands with lamps are positioned on either side, adding functionality to the inviting space.
Hotel room in Fredericksburg
4.83 out of 5 average rating, 178 reviews

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.

Top guest favorite
A spacious game room is showcased, featuring a black pool table in the center. Comfortable gray sofas are positioned along the walls. A large screen is mounted above the bar area, complemented by several high-top stools, creating an inviting space for socializing and entertainment.
Casa particular in Gloucester Township
5 out of 5 average rating, 33 reviews

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.

Top guest favorite
A watercolor painting depicts a serene waterfront scene with boats on the water. A historic yellow building is visible, surrounded by trees and additional structures. The tranquil atmosphere is enhanced by the clear skies and gentle ripples reflecting light on the surface.
Hotel room in Oxford
4.97 out of 5 average rating, 150 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.

Top guest favorite
A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.
Casa particular in Chestertown
4.93 out of 5 average rating, 167 reviews

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!

Top guest favorite
An aerial view captures a vibrant blue pool surrounded by lounge chairs and umbrellas. Several guests enjoy the water, with expansive outdoor seating areas visible on the patio. A sunny environment enhances the inviting atmosphere of the property, framed by lush greenery.
Hotel room in Rehoboth Beach
4.91 out of 5 average rating, 141 reviews

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!

Guest favorite
Hotel room in New Castle
4.89 out of 5 average rating, 115 reviews

“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.

Top guest favorite
A private deck features a vibrant red tray with two white plates, surrounded by lush green plants and colorful flowers. A striped cushion adds a pop of color to a nearby chair, while a scenic view of the golf course is visible beyond the railing.
Resort in Williamsburg
4.94 out of 5 average rating, 264 reviews

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

Top guest favorite
A classic multi-story retreat is framed by lush greenery and neatly landscaped grounds. The spacious front porch, furnished with rocking chairs, welcomes guests. A circular garden bed, adorned with colorful flowers, enhances the inviting exterior under a clear blue sky.
Hotel room in Cape Charles
4.97 out of 5 average rating, 199 reviews

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 favorite
A charming boutique inn is depicted, featuring a classic white exterior with dark shutters and a welcoming sign. Lush gardens with colorful flowers border the property, while large windows allow natural light into the building. The inviting front porch is visible, enhancing the overall aesthetic.
Hotel room in Onancock
4.85 out of 5 average rating, 143 reviews

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!!

Top guest favorite
The entrance to The Terry House is framed by a sturdy black door adorned with intricate carvings. A welcoming sign hangs beside the door, and the steps are flanked by neatly trimmed shrubs in black planters, adding an inviting touch to the historic brick façade.
Hotel room in New Castle
4.95 out of 5 average rating, 169 reviews

“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.

Guest favorite
A collection of boats is docked along the marina, with a variety of boat sizes and styles visible. Lush green trees are seen in the background, complementing the tranquil water. A large covered area provides protection for additional vessels.
Private room in Richmond
4.9 out of 5 average rating, 268 reviews

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.

A spacious room is furnished with a large bed, a comfortable armchair, and a stylish sofa. Natural light enters through large windows with light-filtering curtains. A coffee table sits in the center, accompanied by a decorative lamp. A television is positioned on a low cabinet.
Hotel room in Washington
4.77 out of 5 average rating, 83 reviews

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.

Popular amenities for hotel rentals near Chesapeake Bay

Quick stats about hotel rentals near Chesapeake Bay

  • Total rentals

    160 properties

  • Nightly prices starting at

    ﺩ.ﺇ37 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

Destinations to explore