Holiday resort rentals near Chesapeake Bay

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Top-rated resort rentals near Chesapeake Bay

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The exterior of a multi-story beachfront building is shown, overlooking a sandy beach and the Atlantic Ocean. Bright blue skies and calm waters create a serene backdrop, while colorful umbrellas and beachgoers are visible along the shore.
Resort in Virginia Beach
5 out of 5 average rating, 3 reviews

Discount/Oceanaire/BeachFront/DoubleSuite (Cap 7)

OCEANAIRE - Direct view of Atlantic Ocean; Steps away from the Beach. Featuring 3 seaside pools and bar, this resort is located on Boardwalk, has 32" flat screen cableTV in each unit. State of the art gym with floor to ceiling windows. In heart of Virginia Beach's lively tourist district. Sleeps: 7- 8 people (1 or 2 families can share cost) 2 separate lockout units/bedroom 2 private oceanview balconies 2 kitchens (1 kichenette) 2 luxurious bathrooms $0 parking 1-block garage Highly discounted.

Top guest favourite
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
4.92 out of 5 average rating, 60 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.

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.

A dining area is shown with a long table set for six, featuring colorful chairs. The kitchen is visible in the background, displaying modern appliances and wooden cabinets. The hallway leads to a door, illuminated by natural light from the outside.
Resort in Williamsburg
5 out of 5 average rating, 3 reviews

Historic Williamsburg: Do all the things! & Enjoy

*PLEASE READ *check-in ONLY on Fri, Sat or Sun *The stays are groups of 7 days ; early chk out is ok, but for late chk-in up to 48 hrs, you HAVE to let the resort know in advance!! My vaca pkg gives me access to most resorts in the Williamsburg area. Availability, and resort options change frequently, so pls message, I will look for you. My vaca pkg gives access to many other places across the USA, the rest of the world, cruises, etc REQUIRED:*refundable deposit *resort fee

Top guest favourite
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
4.95 out of 5 average rating, 277 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

Guest favourite
An indoor swimming pool is surrounded by large arched windows that allow natural light to fill the space. Comfortable lounge chairs are positioned along the pool's edge, offering a relaxing area to unwind.
Resort in Williamsburg
4.92 out of 5 average rating, 60 reviews

Charming 1BR Colonial Condo at Wyndham Kingsgate

Welcome to our charming 1BR/1BA condo close to Williamsburg! Located just minutes from historic Williamsburg, you can explore the area or stay on property and relax by the pool and enjoy the many family friendly amenities on site. Experience all that Williamsburg has to offer from historic landmarks along one of Williamsburg's many walking and biking trails like Powhatan Creek Trail, Historic Jamestown Bike Trail, and Freedom Park, historic downtown Williamsburg, and Busch Gardens.

An indoor area features a circular hot tub surrounded by plants and simple seating. Large windows offer views of the outdoors, allowing natural light to brighten the space. The floor is tiled, and ventilation is provided by ceiling fans.
Hotel room in Virginia Beach
4.51 out of 5 average rating, 53 reviews

Near Virginia Beach Boardwalk! Free Parking!

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
Resort in Williamsburg
4.8 out of 5 average rating, 5 reviews

The Historic Powhatan Resort 4 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.

Superhost
A row of charming two-story condos is visible in a well-maintained landscape. Lush green shrubs and neatly trimmed hedges line the pathway, while vibrant trees add bursts of color against a clear blue sky.
Resort in Williamsburg
4.89 out of 5 average rating, 166 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.

Superhost
A private bedroom is furnished with three beds featuring memory foam toppers. A small chair sits near a window that showcases a sunset view over the water. Soft natural light fills the room, complemented by bedside lamps providing warm illumination.
Resort in North East
4.87 out of 5 average rating, 23 reviews

Breathtaking Beauty | Deluxe Room @ Sandy Cove

The private bedroom with 3 beds with comfortable 3-inch memory foam topper for a great night sleep. Leave your cares behind as each night includes standard 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.

Guest favourite
An outdoor swimming pool is framed by lounge chairs and umbrellas, inviting relaxation. A gentle slope is designed for accessibility, and the surrounding area is paved with textured tiles. Nearby, a multi-story building rises, featuring balconies overlooking the pool.
Resort in National Harbor
5 out of 5 average rating, 14 reviews

National Harbor Resort - 2 Bedroom Mobility

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 restaurants.

Guest favourite
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, 55 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 holiday rentals

    Explore 30 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $298 SGD per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Holiday rentals with a pool

    30 properties feature pools

  • Wifi availability

    30 of Chesapeake Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.7 Average rating

    Chesapeake Bay stays receive an average rating of 4.7 out of 5 from guests

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