Resort vacation rentals near Chesapeake Bay

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Top-rated resort rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A well-appointed room features a spacious King bed, paired with a small sleeper sofa. Natural light enters through sliding glass doors leading to the private porch, which overlooks lush greenery. A wooden dresser and seating area add to the comfort of the space.
Resort in James City County
4.91 out of 5 average rating, 56 reviews

Fairway View King Room.

Enjoy this stylish room furnished with a King bed and small sleep sofa. Amenities include a private bath, mini fridge and Keurig coffee. Relax sipping coffee on the private porch overlooking the 9th Fairway of the famous River Course. A swimming pool on-site is available in season. Our unit is not enrolled in the Kingsmill Resort Program. The private club amenities such as golf & sports center are not available. You will have access to "The Mill" Coffee shop , The SPA and Marina/Beach areas.

Aerial view of the Ocean Beach Club property, showcasing its modern architecture with green roofs. The blue Atlantic Ocean and sandy beach are visible in the background, with beach umbrellas dotting the shore and a lively street lined with palm trees in the foreground.
Resort in Virginia Beach
5 out of 5 average rating, 3 reviews

Ocean Beach Club during Neptune Festival!

Available Sept 30-Oct 7, 2022. Experience Virginia Beach from an Ocean Beach Club high-end 2 Bedroom Oceanfront Suite. Enjoy 4 oceanfront pools, poolside dining, and the 17th-fl. fitness center overlooking the Atlantic. Guests also enjoy amenities at sister property Oceanaire Resort Hotel. • Wi-Fi • Game Rm & Arcade • Business Ctr • Valet Parking • Laundry onsite Oceanaire: • Ultra Craft Cocktails • Aqua 21-oceanfront, adult-only indoor infinity pool with bar service • sun deck & lounge

Guest favorite
The resort exterior is showcased with charming architecture and well-maintained landscaping. The building features multiple levels, balconies, and walking paths surrounded by trees and shrubs, all bathed in the warm hues of dusk.
Resort in Williamsburg
4.83 out of 5 average rating, 12 reviews

Club Wyndham Governor’s Green One-Bedroom Suite

This conveniently located resort is the perfect place to access the best attractions and activities in Williamsburg. Unwind in your quaint one-bedroom resort suite that offers a private bedroom, fully equipped kitchen, living/dining area and a washer/dryer that will enhance your stay. Take the children to play at one of two playgrounds and enjoy three swimming pools, three hot tubs, a day spa, miniature golf, a billiards room, fitness center, massage, a tour desk and activities program.

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, 266 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

A wide view of the Virginia Beach shoreline displays golden sand meeting the ocean's shimmering waters. Colorful beach umbrellas are arranged on a patio, surrounded by lush landscaping, while a pedestrian walkway runs parallel to the beach, inviting leisurely strolls. The nearby pier extends into the ocean.
Hotel room in Virginia Beach
4.83 out of 5 average rating, 6 reviews

Sun, Sand, and Surf! Kitchen, Onsite Pool

In the heart of the boardwalk area of Virginia Beach, this property offers an ideal location for your beach getaway. Step outside and explore miles of shops and restaurants along the boardwalk. Head to the nearby pier for some fishing. Rent a kayak or or soar over the beach in a parasail. Check out a local museum. Or just spend your day relaxing on the sand, beachside. There’s so much to see and do, and it’s all right outside your door!

Superhost
The exterior of the resort building is showcased, featuring a modern design with rounded architectural elements. The Beach Quarters sign is prominently displayed. Lush greenery and colorful flower beds enhance the entrance, while a spacious parking structure is visible in the background.
Resort in Virginia Beach
4.5 out of 5 average rating, 4 reviews

1 Bedroom Suite Oceanfront with ocean view

"Stay for the whole week and receive 15% discount" (covers more than Airbnb fee). The timeshare I own is week 24 (Sat-Sat) a 1 bedroom suite oceanfront ocean view from the balcony, free parking attached to the resort building (overflow & Large vehicles parking across the street). Free in room WiFi, game room, tennis court, daily activities, boardwalk. Walk out the door straight to the beach. You need room key to access the building.

Superhost
Resort in Williamsburg
4.65 out of 5 average rating, 17 reviews

The Historic Powhatan Resort 2 bdrm

Turn back the pages of time and become immersed in the Colonial spirit of Williamsburg, a historic city steeped in tradition and forever preserved as part of our nation’s history. Discover this 170-acre Early American town featuring 18th-century English architecture restored to its original condition, historic museums, monuments and fascinating battlefields which tell the dramatic story of our country’s birth.

Guest favorite
A row of well-maintained two-story condos is presented, featuring light-colored exteriors and distinct rooflines. Lush green landscaping with manicured shrubs and small trees adds a vibrant touch. A clear blue sky and soft clouds enhance the welcoming atmosphere of the property.
Resort in Williamsburg
4.89 out of 5 average rating, 181 reviews

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

Turn back the pages of time and become immersed in the Colonial spirit of Williamsburg, a historic city steeped in tradition and forever preserved as part of our nation’s history. Discover this 170-acre Early American town featuring 18th-century English architecture restored to its original condition, historic museums, monuments and fascinating battlefields which tell the dramatic story of our country’s birth.

An outdoor swimming pool is surrounded by a spacious deck with numerous lounge chairs. Umbrellas provide shade, and tall pine trees create a natural backdrop, enhancing the serene environment of the resort.
Resort in Williamsburg
4.67 out of 5 average rating, 15 reviews

Wyndham Patriots Place | King Bed Studio

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. Wyndham Patriots Place | King Bed Studio • Size: 380 - 380 • Kitchen: Mini • Baths: 1 • Accommodates: 2 Guests • Beds: King Bed - 1

Superhost
A serene aerial view captures the retreat center situated along the bay at sunset, with soft hues of purple and pink reflected on the calm water. A wooden pier extends into the bay, complementing the lush greenery and manicured lawns surrounding the buildings.
Resort in North East
4.85 out of 5 average rating, 13 reviews

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Guests refer to Sandy Cove's 220 acres as the most peaceful, relaxing, breathtaking place on the headwaters of the Chesapeake Bay. Leave your cares behind as each night includes deluxe lodging & fun activities. Recipient of TripAdvisor's Certificate of Excellence, we offer a unique blend of Christian hospitality & amazing lodging with endless opportunity to meet your vacation needs.

An outdoor swimming pool is framed by lounge chairs and features a wheelchair-accessible lift. The surrounding area is paved and includes several light posts. A multi-story building is visible in the background, showcasing a combination of balconies and large windows.
Resort in Oxon Hill
4.88 out of 5 average rating, 59 reviews

National Harbor Resort - 1 Bedroom Deluxe

Waterfront Escape at National Harbor | Rooftop Terrace + Marina Enjoy vibrant waterfront living just minutes from downtown Washington, D.C. After a day of sightseeing, unwind in the indoor pool, take in skyline views from the rooftop terrace, or stroll the marina filled with shops and restaurantes.

A welcoming sign for Patriots' Place is prominently displayed among landscaped greenery. Surrounding the sign, white flowers bloom in a neatly maintained flower bed, set against a backdrop of trees and a clear sky.
Resort in Williamsburg
4.96 out of 5 average rating, 52 reviews

Patriot's Place Resort - 2 Bedroom Lockoff

Historic Williamsburg Near Busch Gardens | Golf + Fire Pit Step back in time with modern comforts at this colonial-style retreat. Surrounded by tall trees, it’s minutes from Colonial Williamsburg, Busch Gardens, and top golf. After exploring, unwind by the fire pit or relax on your private patio.

Popular amenities for resort rentals near Chesapeake Bay

Quick stats about resort rentals near Chesapeake Bay

  • Total rentals

    30 properties

  • Nightly prices starting at

    € 198 before taxes and fees

  • Total number of reviews

    130 reviews

  • Rentals with a pool

    30 properties have a pool

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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