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.

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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.

An outdoor pool reflects the vibrant colors of a sunset, surrounded by lounge chairs and shaded seating areas. A nearby building with a patio features umbrellas, offering a relaxing atmosphere. The horizon shows a warm glow as the day transitions to evening.
Resort in Virginia Beach
5 out of 5 average rating, 3 reviews

[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

Top Guest favourite
The exterior of a two-story house is visible, featuring gray shingles and multiple windows. Well-maintained landscaping includes bushes and a grassy area. A large tree in the foreground provides shade, enhancing the inviting appearance of the property.
Resort in James City County
4.92 out of 5 average rating, 63 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
4.57 out of 5 average rating, 49 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
Resort in Williamsburg
4.95 out of 5 average rating, 280 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
Resort in Williamsburg
5 out of 5 average rating, 8 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.

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
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 spacious outdoor pool area is illuminated in soft lighting, featuring lanes marked by blue tiles. Surrounding the pool are lounge chairs and shaded seating areas, with a nearby building offering additional amenities. Lush greenery frames the scene under a twilight sky.
Resort in Williamsburg
4.9 out of 5 average rating, 10 reviews

The Historic Powhatan 3 bdrm

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.

Guest favourite
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
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.

Resort in Oxon Hill
4.88 out of 5 average rating, 60 reviews

National Harbor Resort - 1 Bedroom Deluxe

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.

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 $325 AUD 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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