
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.

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.

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.

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.

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!

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.

Sun, Sand, and Surf! Kitchen, Onsite Pool
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!

*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.

Comfy 1-Room 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.

National Harbor • Pool + Dc Waterfront Stay
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 restaurantes.

Wyndham Governor's Green - 3 Bedroom Deluxe
Resort by Colonial Williamsburg | Pool + Fire Pit Enjoy peaceful surroundings and modern comforts at this charming resort just minutes from Colonial Williamsburg and historic sites. After a day of exploring, relax by the pool, stroll the landscaped grounds, or gather around the fire pit.
Popular amenities for resort rentals near Chesapeake Bay
Family-Friendly Resort Stays

The Historic Powhatan Resort - 1 Bedroom Upstairs

Discount/Oceanaire/BeachFront/DoubleSuite (Cap 7)

Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

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

Historic Williamsburg: Do all the things! & Enjoy

Charming 3BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor|4BR/4BA King Pres Suite
Resort rentals with a pool

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

Charming 2BR Colonial Condo at Wyndham Kingsgate

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

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
Resort rentals with a gym

Wyndham Governor's Green - 2 Bedroom Deluxe

Wyndham Governor's Green - 2 Bedroom Deluxe

Kingsgate Resort- 1 bedroom

Wyndham Governor's Green - 2 Bedroom Deluxe

*Historic Powhatan Resort- 4 bedroom sleeps 12

Charming 2BR Colonial Condo at Wyndham Kingsgate

Historic Powhatan Resort- 4 bedrooms

Charming 2BR Colonial Condo at Wyndham Kingsgate
Other resort holiday rentals

Great Unit, Ocean Front, Free Parking!

Club Wyndham Governor’s Green One-Bedroom Suite

Beautiful Bayview 2-Room Master Suite @ Sandy Cove

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Estate-Style Stay with Plush King Bed & Tub

The Mayflower

The Santa Maria

USS Lawson
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 $388 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, 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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- Resort rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
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