
Resort holiday rentals near Chesapeake Bay
Find and book unique resort stays on Airbnb
Top-rated resort rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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

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.

Hilton Virginia Beach 3BR Penthouse with oceanview
Furnished 2 level condo, 3 BR Penthouse suite with ocean views. Each bedrooms have balcony, full kitchen with dishwasher and garbage disposal, a dining room balcony with table and seats for outdoor dining (which makes a total of 4 balconies), a washer and dryer in the room, a fireplace in the living room, a 2 story window in the living room, a beautiful spiral staircase, high speed internet, DVD player, and TV's in each bedroom and living room. Comes with two free parking spaces.

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.

Beach front resort in beautiful Virginia Beach
Hotel details This casual, beachfront hotel with airy rooms feature free Wi-Fi, flat-screen TVs and DVD players, plus kitchenettes and balconies. Suites add living rooms with pull-out sofas and full kitchens. In addition to a seasonal cafe, tiki bar, amenities include 3 oceanfront pools and 1 kids' pool, an adults-only infinity pool), laundry facilities, a business center and conference rooms, and there's also a 17th-floor fitness center with ocean views.

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.

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.

Estate-Style Stay with Plush King Bed & Tub
Experience a perfect getaway with family-friendly luxury accommodations just minutes from thrilling Busch Gardens and historic Colonial Williamsburg. Enjoy activities like tennis, miniature golf, and relaxing in saunas. A short drive from Newport News/Williamsburg Airport, this gem offers easy access to Water Country USA and captivating Historic Jamestowne. Ideal for families, history buffs, and adventure seekers.
Popular amenities for resort rentals near Chesapeake Bay
Family-Friendly Resort Stays

The Historic Powhatan Resort - 1 Bedroom Upstairs

Wyndham National Harbor | 3BR/2BA King Bed Suite

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor | 2BR/2BA King Bed Suite

Charming 1BR Colonial Condo at Wyndham Kingsgate

Historic Williamsburg: Do all the things! & Enjoy

Wyndham Kingsgate - 1 Bedroom Suite

Charming 3BR Colonial Condo at Wyndham Kingsgate
Resort rentals with a pool

Wyndham National Harbor | 2BR/2BA King Bed Suite

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Beautiful Bayview 2-Room Master Suite @ Sandy Cove

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor | 2BR/2BA King Bed Suite

Historic Powhatan Resort- 4 bedrooms

Charming 2BR Colonial Condo at Wyndham Kingsgate

Breathtaking Beauty | Deluxe Room @ Sandy Cove
Resort rentals with a gym

Wyndham Governor's Green - 2 Bedroom Deluxe

Wyndham Governor's Green - 2 Bedroom Deluxe

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham Governor's Green - 2 Bedroom Deluxe

Wyndham Governor's Green - 2 Bedroom Deluxe

Club Wyndham Governor’s Green Three-Bedroom Suite

Wyndham Kingsgate Resort | 1BR/1BA King Bed Suite

Wyndham Governor's Green - 2 Bedroom Deluxe
Other resort holiday rentals

Sun, Sand, and Surf! Kitchen, Onsite Pool

St. Michaels Harbour Inn - 2 Queen WF Suite

Kings Creek Plantation Resort 4 1/2 Star Rating

St. Michaels Harbour Inn - 2 Queen WF Suite

St. Michaels Harbour Inn - Premium King WF Suite

Wyndham Kingsgate - 2 Bedroom Deluxe

National Harbor Resort - 1 Bedroom Deluxe

Hilton Virginia Beach 2BR Suite city view
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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- Resort rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- First Landing Beach
- Hampton University
- Old Dominion University
- Chrysler Hall
- Virginia Living History Museum
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park




