Resort holiday rentals near Chesapeake Bay

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.

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!

1 BR Suite Oceanfront on 4th of July week

Note: Available on the 4th of July week (Sat- Sat) on the 10th floor at Beach Quarters Resort, oceanfront, full ocean view property. 1 bedroom and studio suite with full ocean view from the bedroom and living room balconies. Free parking attached to the resort building (overflow & large vehicle parking across the street). Walk out the door straight to the beach. You can watch the firework from the private balcony.

*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.

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.

6/27-7/4/25 Ocean Penthouse Suite 3B/3B - reduced

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 27- July 4, 2025 (7 nights)

Patriot's Place Resort - 1 Bedroom Suite

Guests will discover all the convenient vacation amenities and recreation activities that ensure your travels are unforgettable and stress-free. Stay fit while enjoying recreational sports like swimming, and basketball. Choosing Club Wyndham Patriots' Place will give memories that last a lifetime.