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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Top Guest favourite
Resort in James City County
4.93 out of 5 average rating, 76 reviews

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.

Resort in Williamsburg
4.67 out of 5 average rating, 78 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.

An aerial view captures the resort's waterfront location, featuring a pristine pool surrounded by lounge chairs. The marina is visible, lined with boats docked along wooden piers, while the resort building presents a modern architectural design.
Resort in Saint Michaels
4.85 out of 5 average rating, 27 reviews

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.

Guest favourite
A vibrant sunset paints the sky in shades of pink, orange, and purple, with the sun descending towards the horizon over the bay. Silhouettes of nearby buildings and trees frame the scene, enhancing the serene waterfront view.
Resort in Ocean City
4.96 out of 5 average rating, 49 reviews

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!

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
4.94 out of 5 average rating, 307 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 large windows, allowing natural light to fill the space. Comfortable lounge chairs are arranged along the pool's edge, with a light blue and yellow color scheme enhancing the inviting environment.
Resort in Williamsburg
4.83 out of 5 average rating, 40 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
4.92 out of 5 average rating, 12 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!

Guest favourite
A row of charming two-story condos is visible in a well-maintained landscape. Lush green shrubs and neatly trimmed hedges line the pathway, while vibrant trees add bursts of color against a clear blue sky.
Resort in Williamsburg
4.89 out of 5 average rating, 178 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
An aerial view showcases the serene waterfront property at dusk, with a picturesque sky reflecting purples and oranges over calm waters. The building layout is outlined against lush greenery, while a pier extends into the bay, adding to the tranquil ambiance.
Resort in North East
5 out of 5 average rating, 3 reviews

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.

Resort in Oxon Hill
4.92 out of 5 average rating, 12 reviews

National Harbor • Pool + Dc Waterfront Stay

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.

Superhost
Resort in Williamsburg
5 out of 5 average rating, 3 reviews

Wyndham Governor's Green - 3 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 $388 NZD 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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