
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.

[Oceanfront] 1-bedroom (sleeps 6) /Virginia Beach/
Oceanfront 6th Floor Balcony One Bedroom Sleeps 6 Size 455 ft Free WiFi, cable & flat screen TV, sitting area and pullout sofa bed. Private kitchen: Refrig, Microwave, Stovetop, Oven, Kitchenware, Dishwasher. Private bathroom: Bathtub, Free toiletries, toilet, Shower. Facilities: Linens, Alarm clock, Tea/Coffee maker, safe, Air conditioning, Free public parking. Loaded with Resort amenities. Outdoor/Indoor pools. Bar, Tennis, Exercise facility, programs and activities for all ages. Trolley

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 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.

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.

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 SA-4T
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.

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!

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.

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.

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.

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
Family-friendly resort rentals

The Historic Powhatan Resort - 1 Bedroom Upstairs

Discount/Oceanaire/BeachFront/DoubleSuite (Cape 7)

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

Historic Williamsburg: Do all the things! & Enjoy

Charming 3BR Colonial Condo at Wyndham Kingsgate
Resort rentals with a pool

Beautiful Bayview 2-Room Master Suite @ Sandy Cove

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Charming 2BR Colonial Condo at Wyndham Kingsgate

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

Historic Powhatan Resort- 4 bedrooms

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 2BR Colonial Condo at Wyndham Kingsgate

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

Wyndham Governor's Green - 2 Bedroom Deluxe

Wyndham Governor's Green - 2 Bedroom Deluxe

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham Governor's Green - 2 Bedroom Deluxe

Wyndham Governor's Green - 2 Bedroom Deluxe

Charming 1BR Colonial Condo at Wyndham Kingsgate

Governor's Green Resort - 2 Bedroom Deluxe

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

Wyndham Kingsgate - 2 Bedroom Deluxe

Wyndham Kingsgate - 1 Bedroom Suite

St. Michaels Harbour Inn - Premium King WF Suite

Estate-Style Stay with Plush King Bed & Tub

Wyndham Kingsgate - 1 Bedroom Suite

Wyndham Kingsgate - 2 Bedroom Deluxe

Club Wyndham Governor’s Green Three-Bedroom Suite

Breathtaking Beauty | Deluxe Room @ 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 £163 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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- Resort rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- First Landing Beach
- Hampton University
- Town Point Park
- Old Dominion University
- Chrysler Hall
- Virginia Living History Museum
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park




