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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Top guest favorite
Resort in James City County
4.93 out of 5 average rating, 75 reviews

Fairway View King Room.

Enjoy this stylish room furnished with a comfortable King bed . Located in a peaceful area within a gated community but very close to Busch Gardens. Also, the historic Colonial Williamsburg is just a quick 2 minute drive away. Amenities include a bath/shower 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. This unit is NOT enrolled in the Kingsmill Resort Program.

Resort in Williamsburg
4.68 out of 5 average rating, 77 reviews

Club Wyndham Governor’s Green Three-Bedroom Suite

This conveniently located resort is the perfect place to access the best attractions and activities in Williamsburg. Unwind in your quaint three-bedroom resort suite that offers private bedrooms, 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.

An aerial view captures the resort's waterfront location, featuring a pristine pool surrounded by lounge chairs. The marina is visible, lined with boats docked along wooden piers, while the resort building presents a modern architectural design.
Resort in Saint Michaels
4.85 out of 5 average rating, 27 reviews

St. Michaels Harbour Inn - Waterfront King Room

Indulge in history by staying at St. Michaels Harbour Inn- a full-service resort in downtown St. Michaels, MD. Amenities include a restaurant & bar, day spa, car service, bicycles & unbeatable views. Our Waterfront Spa Tub Rooms provide comfort & relaxation amidst the historic backdrop of the St. Michaels harbor featuring a king bed, jacuzzi tub & floor-to-ceiling windows overlooking the harbor. *Please note that occupancy tax (4%) will be collected in addition to your nightly rate.

Guest favorite
An outdoor pool area is depicted with a vibrant tile design and several lounge chairs arranged along the side. Umbrellas provide shade, while the sunset casts soft light over the water, offering a tranquil setting for relaxation.
Resort in Ocean City
4.96 out of 5 average rating, 49 reviews

Amazing Bayside Views @Sunset309

Incredible Bayside sunset views in this 4 person, 1 bedroom, 1 bath beautifully decorated unit at the Coconut Malorie! NEWLY REMODELED FOR 2023! This fun and well-appointed condo features: - Private bedroom with queen bed, newly remodeled large kitchenette with everything you need to serve family and friends, 65-inch smart TV's, beach chairs, beach umbrella, large tile bathroom with shower and jetted spa tub, rainfall shower head, hair dryer, and large vanity mirror and outdoor pool!

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, 304 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 surrounded by large windows, allowing natural light to fill the space. Comfortable lounge chairs are arranged along the pool's edge, with a light blue and yellow color scheme enhancing the inviting environment.
Resort in Williamsburg
4.82 out of 5 average rating, 38 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.

The outdoor swimming pool is framed by a spacious deck with lounge chairs. A large, well-designed building features high ceilings and multiple windows, providing a welcoming hub for guests. Surrounding greenery adds a touch of nature to the serene setting.
Resort in Williamsburg
4.86 out of 5 average rating, 7 reviews

Kings Creek Plantation Resort - 4 1/2 Star SA-T2

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 & Entertainment Venues. 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.

Hotel room in Virginia Beach
4.49 out of 5 average rating, 35 reviews

Great Unit, Ocean Front, 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
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
4.85 out of 5 average rating, 33 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.

Hotel room in Williamsburg
4.5 out of 5 average rating, 6 reviews

2BR Deluxe Stay w/ Whirlpool Tub & Private Deck

Experience a perfect getaway with family-friendly luxury accommodations just minutes from thrilling Busch Gardens and historic Colonial Williamsburg. Enjoy activities like tennis, miniature golf, and relaxing in saunas. A short drive from Newport News/Williamsburg Airport, this gem offers easy access to Water Country USA and captivating Historic Jamestowne. Ideal for families, history buffs, and adventure seekers.

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
4.88 out of 5 average rating, 193 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 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.

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$46,036 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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