
Holiday resort 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.

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.

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.

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.

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

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

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.

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!

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.

*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.

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.

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.

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
Family-friendly resort rentals

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

Wyndham Patriots Place | King Bed Studio

Charming 1BR Colonial Condo at Wyndham Kingsgate

St. Michaels Harbour Inn - Premium King WF Suite

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor|4BR/4BA King Pres Suite

Wyndham Kingsgate Resort | 1BR/1BA King Bed Suite

Ocean Beach - Studio
Resort rentals with a pool

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham Patriots Place | 1BR/1BA King Bed Suite

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor | 2BR/2BA King Bed Suite

Charming 3BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham Patriots Place | King Bed Studio
Resort rentals with a gym

Wyndham National Harbor | 3BR/2BA King Bed Suite

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor | 2BR/2BA King Bed Suite

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

Charming 2BR Colonial Condo at Wyndham Kingsgate

1 Bedroom Suite Oceanfront with ocean view

Wyndham National Harbor | 2BR/2BA King Bed Suite

*Historic Powhatan Resort- 2 Bedroom Sleeps 6
Other resort holiday rentals

Governor's Green Resort - 3 Bedroom Deluxe

Beach Quarters Resort - Ocean Front Studio

Beautiful Bayview 2-Room Master Suite @ Sandy Cove

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Governor's Green Resort - 3 Bedroom Deluxe

Governor's Green Resort - 2 Bedroom Deluxe

Comfy 1-Room Suite @ Sandy Cove

Wyndham Patriots Place | 2BR/2BA King Bed Suite
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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