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Holiday resort 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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A spacious balcony overlooks a sandy beach and the ocean, where colorful umbrellas and beachgoers are visible. The expansive sky is bright with soft clouds, creating a serene coastal view.
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
Resort in James City County
4.93 out of 5 average rating, 69 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.

The resort exterior is showcased with charming architecture and well-maintained landscaping. The building features multiple levels, balconies, and walking paths surrounded by trees and shrubs, all bathed in the warm hues of dusk.
Resort in Williamsburg
4.89 out of 5 average rating, 18 reviews

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.

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.

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, 293 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

Guest favourite
An indoor swimming pool is surrounded by large arched windows that allow natural light to fill the space. Comfortable lounge chairs are positioned along the pool's edge, offering a relaxing area to unwind.
Resort in Williamsburg
4.93 out of 5 average rating, 69 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 swimming pool is surrounded by lounge chairs, set against a backdrop of a spacious white building with large windows. Lush greenery and colorful foliage enhance the relaxing environment, while bright blue skies provide a serene atmosphere.
Resort in Williamsburg
4.8 out of 5 average rating, 5 reviews

Kings Creek Plantation Resort 4 1/2 Star SA-4T

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 & Entertainment Venues. 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
4.9 out of 5 average rating, 10 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.

Superhost
Three multi-story buildings are situated beside a calm pond, with a fountain creating gentle ripples on the water's surface. The buildings feature balconies and symmetrical architecture, all reflecting against the water, set against a clear blue sky.
Resort in Williamsburg
4.84 out of 5 average rating, 32 reviews

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.

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.

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
4.56 out of 5 average rating, 18 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.

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 £163 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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