
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.

Fairway View King Room.
Enjoy this stylish room furnished with a King bed and small sleep sofa. 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.

Historic Williamsburg: Do all the things! & Enjoy
*PLEASE READ *check-in ONLY on Fri, Sat or Sun *The stays are groups of 7 days ; early chk out is ok, but for late chk-in up to 48 hrs, you HAVE to let the resort know in advance!! My vaca pkg gives me access to most resorts in the Williamsburg area. Availability, and resort options change frequently, so pls message, I will look for you. My vaca pkg gives access to many other places across the USA, the rest of the world, cruises, etc REQUIRED:*refundable deposit *resort fee

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.

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.

Club Wyndham National Harbor Three-Bedroom Deluxe
Welcome to Club Wyndham National Harbor - located along the banks of the Potomac and just minutes from Washington, D.C. This resort offers a three-bedroom resort suite that features a full kitchen and separate living/dining areas. Select suites include a whirlpool tub and private balcony. Enjoy the amenities, including the indoor/outdoor pools, children's pool, hot tub, fitness center, game room and laundry facilities onsite.

2 Family-Friendly Units Near Trails & Museums
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.

*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.

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.

The Historic Powhatan Resort 1 bdrm
Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony. You will check in at a building that was originally built circa 1735, this restored manor house.

Historic Powhatan Resort- 4 bedrooms
Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

1BR-2BA Oceanview Condo with 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
Family-Friendly Resort Stays

St. Michaels Harbour Inn - 2 Queen WF Suite

Wyndham Patriots Place | King Bed Studio

The Historic Powhatan Resort - 1 Bedroom Upstairs

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate

Kings Creek Plantation Resort 4 1/2 Star Rating

Charming 1BR Colonial Condo at Wyndham Kingsgate

Ocean Beach - Studio
Resort rentals with a pool

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham Patriots Place | 1BR/1BA King Bed Suite

Charming 1BR Colonial Condo at Wyndham Kingsgate

Wyndham National Harbor|4BR/4BA King Pres Suite

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

Wyndham Patriots Place | 2BR/2BA King Bed Suite

Wyndham Patriots Place | King Bed Studio

Wyndham Patriots Place | King Bed Studio
Resort rentals with a gym

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

Charming 1BR Colonial Condo at Wyndham Kingsgate

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

Charming 2BR Colonial Condo at Wyndham Kingsgate

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

Charming 3BR Colonial Condo at Wyndham Kingsgate

Charming 2BR Colonial Condo at Wyndham Kingsgate

Charming 2BR Colonial Condo at Wyndham Kingsgate
Other resort holiday rentals

Beach Quarters Resort - Ocean Front Studio

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

*Historic Powhatan Resort- 4 bedroom sleeps 12

Wyndham Patriots Place | 2BR/2BA King Bed Suite

Beautiful Bayview 2-Room Master Suite @ Sandy Cove

Stunning Bayview, 2-Room Deluxe Suite @ Sandy Cove

Wyndham Patriots Place | 2BR/2BA King Bed Suite

*Historic Powhatan Resort- 2 Bedroom Sleeps 6
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 $345 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, Wi-Fi 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
Destinations to explore
- Bed and breakfasts Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Condo rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Resort rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




