
Resort holiday 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.

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.

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.

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!

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.

*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.

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.

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.

Historic Powhatan Resort- 4 bedrooms
Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony. Originally built circa 1735, this restored manor house offers a serene getaway during any season.
Popular amenities for resort rentals near Chesapeake Bay
Family-Friendly Resort Stays

St. Michaels Harbour Inn - Premium King WF Suite

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

Historic Williamsburg: Do all the things! & Enjoy

Charming 2BR Colonial Condo at Wyndham Kingsgate

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate
Resort rentals with a pool

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

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

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

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

Charming 3BR Colonial Condo at Wyndham Kingsgate

Wyndham Kingsgate Resort | 1BR/1BA King Bed Suite
Resort rentals with a gym

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

Kingsgate Resort- 1 bedroom

*Historic Powhatan Resort- 4 bedroom sleeps 12

The Historic Powhatan Resort 1 bdrm

Governor's Green Resort - 2 Bedroom Deluxe

Governor's Green Resort - 3 Bedroom Deluxe

The Historic Powhatan Resort- 2 bdrm

Governor's Green Resort - 2 Bedroom Deluxe
Other resort holiday rentals

Governor's Green Resort - 2 Bedroom Mobility

Governor's Green Resort - 3 Bedroom Deluxe

Governor's Green Resort - 2 Bedroom Deluxe

Governor's Green Resort - 3 Bedroom Deluxe

Kingsgate Resort - 1 Bedroom Suite

Governor's Green Resort - 3 Bedroom Deluxe

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Beautiful Bayview 2-Room Master Suite @ Sandy Cove
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 $387 NZD 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

Wi-Fi availability
30 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Resort rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
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- Buckroe Beach
- Outlook Beach
- Norfolk Botanical Garden
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