Holiday resort rentals near Chesapeake Bay

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Top-rated resort rentals near Chesapeake Bay

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The exterior of a multi-story beachfront building is shown, overlooking a sandy beach and the Atlantic Ocean. Bright blue skies and calm waters create a serene backdrop, while colorful umbrellas and beachgoers are visible along the shore.
Resort in Virginia Beach
5 out of 5 average rating, 3 reviews

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.

Top guest favourite
Resort in James City County
4.92 out of 5 average rating, 64 reviews

Fairway View King Room.

Enjoy this stylish room furnished with a comfortable King bed . 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.

Resort in Williamsburg
4.61 out of 5 average rating, 56 reviews

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.

Top guest favourite
A private deck features a vibrant red tray with two white plates, surrounded by lush green plants and colorful flowers. A striped cushion adds a pop of color to a nearby chair, while a scenic view of the golf course is visible beyond the railing.
Resort in Williamsburg
4.95 out of 5 average rating, 281 reviews

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

Superhost
An indoor swimming pool is surrounded by tall windows that allow natural light to fill the space. Lounge chairs line the pool area, creating a relaxed atmosphere. The walls are painted in soft blue, enhancing the tranquil environment.
Resort in Williamsburg
4.68 out of 5 average rating, 19 reviews

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.

An inviting outdoor swimming pool is surrounded by a spacious deck and lounge chairs. A multi-story building with large windows serves as a backdrop, enhanced by trees and shrubs. The clear blue sky reflects a serene atmosphere, completing this recreational setting.
Resort in Williamsburg
4.63 out of 5 average rating, 8 reviews

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.

Hotel room in Virginia Beach
4.88 out of 5 average rating, 8 reviews

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!

Superhost
The exterior of the resort building is showcased, featuring a modern design with rounded architectural elements. The Beach Quarters sign is prominently displayed. Lush greenery and colorful flower beds enhance the entrance, while a spacious parking structure is visible in the background.
Resort in Virginia Beach
4.5 out of 5 average rating, 4 reviews

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.

Guest favourite
A row of charming two-story condominiums is set against a clear blue sky. Lush green lawns and neatly trimmed shrubs surround the buildings, while flowering trees add vibrant color to the landscape, creating a welcoming atmosphere in a well-kept environment.
Resort in Williamsburg
4.87 out of 5 average rating, 144 reviews

*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.

Superhost
A private bedroom is furnished with three beds featuring memory foam toppers. A small chair sits near a window that showcases a sunset view over the water. Soft natural light fills the room, complemented by bedside lamps providing warm illumination.
Resort in North East
4.87 out of 5 average rating, 23 reviews

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.

A private balcony is visible, featuring two woven chairs and a table, overlooking a sandy beach and the ocean. The expansive view is complemented by a clear blue sky and distant ocean waves, creating a serene atmosphere.
Resort in Virginia Beach
4.53 out of 5 average rating, 17 reviews

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.

Guest favourite
A spacious outdoor pool area is surrounded by a patterned stone deck. Lounge chairs are arranged around the pool, which reflects the soft overcast sky. The clubhouse is visible in the background, featuring light-colored siding and architectural details.
Resort in Williamsburg
4.92 out of 5 average rating, 12 reviews

Governor's Green Resort - 2 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

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 $293 SGD 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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