Holiday resort rentals near Chesapeake Bay

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.

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.

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!

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.

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.

*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.

6/26-7/3/26 Ocean Penthouse 3B/3B-$100 off/night

Our 3B/3B penthouse at the Ocean Beach Club has all rooms directly facing the Ocean with two balconies overlooking the ocean. Sleeps 8, full kitchen and living room. Outdoor adult pool & hot tub, kids pool, indoor pool, restaurant on site. Great location - short walk to all the E Street events. Only available June 26 - July 3, 2026 (7 nights). Price has been reduced by $100 per night.

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.