Resort vacation rentals near Chesapeake Bay

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Top-rated resort rentals near Chesapeake Bay

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Top guest favorite
Resort in James City County
4.92 out of 5 average rating, 62 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
4.86 out of 5 average rating, 14 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
4.95 out of 5 average rating, 280 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

Superhost
An indoor swimming pool is featured with clear, blue water reflecting the vaulted ceiling. Lounge chairs line the poolside, and large windows provide ample natural light while offering views of the exterior.
Resort in Williamsburg
4.76 out of 5 average rating, 21 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 inviting outdoor swimming pool is surrounded by a spacious deck and lounge chairs. A multi-story building with large windows serves as a backdrop, enhanced by trees and shrubs. The clear blue sky reflects a serene atmosphere, completing this recreational setting.
Resort in Williamsburg
4.63 out of 5 average rating, 8 reviews

Kings Creek Plantation Resort 4 1/2 Star Rating

Williamsburg with surrounding Jamestown and Yorktown is rich in Historical sites. Enjoy the entertainment and fun at "Busch Gardens" and "Water Country USA". Receive Discounted golf at three spectacular Championship Golf Courses Choose from hundreds of Restaurants, Lounges, Shopping VenuesEntertainment Take the short ride to Virginia Beach for a dip in the Ocean or just take a stroll on the Boardwalk. Note: Check-in Saturday to Saturday Only=7 night minimum stay Only.

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
4.52 out of 5 average rating, 54 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
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
Three multi-story buildings are situated beside a calm pond, with a fountain creating gentle ripples on the water's surface. The buildings feature balconies and symmetrical architecture, all reflecting against the water, set against a clear blue sky.
Resort in Williamsburg
4.84 out of 5 average rating, 31 reviews

Kingsgate Resort- 1 bedroom

You'll want to be as close as possible to the living history that is Colonial Williamsburg®, and Kingsgate is just 2 miles from the historic city. Walk among the shopkeepers, farmers and tradespeople who populated a town on the verge of revolution. Enter their homes and taverns and immerse yourself in their way of life. Whether you choose a guided or self-guided tour, a carriage or a Segway, you'll discover a precious past.

Guest favorite
A serene lake reflects a row of white, multi-story buildings surrounded by lush green trees. The calm water creates a peaceful setting, complemented by the clear blue sky above.
Resort in Williamsburg
4.9 out of 5 average rating, 10 reviews

The Historic Powhatan 3 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 charming two-story condominiums is set against a clear blue sky. Lush green lawns and neatly trimmed shrubs surround the buildings, while flowering trees add vibrant color to the landscape, creating a welcoming atmosphere in a well-kept environment.
Resort in Williamsburg
4.87 out of 5 average rating, 144 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.

A private balcony is visible, featuring two woven chairs and a table, overlooking a sandy beach and the ocean. The expansive view is complemented by a clear blue sky and distant ocean waves, creating a serene atmosphere.
Resort in Virginia Beach
4.53 out of 5 average rating, 17 reviews

One Bed Two Bath Apt - King w/ Sofa bed - Balcony

This fully-equipped one-bedroom condo sleeps up to four guests and features a Queen bed, Queen sofa bed, two bathrooms, and a private balcony, perfect for enjoying fresh ocean breezes. Just steps from the beach, this retreat is ideal for families, couples, or solo travelers seeking comfort and convenience.

Popular amenities for resort rentals near Chesapeake Bay

Quick stats about resort rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 30 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at G$48,094 GYD per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Vacation rentals with a pool

    30 properties feature pools

  • Wi-Fi availability

    30 of Chesapeake Bay vacation rentals include wi-fi 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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