Search Best Resorts in Chesapeake Bay

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Resort in Chesapeake Bay

Hilton Vacation Club The Historic Powhatan Williamsburg
Relax by the pool surrounded by a deck and lounge chairs, with a covered pavilion nearby.

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 star property
9.0 out of 10, Wonderful, (2886)
"We loved this property and how convenient it was to all the attractions! "
The price is AU$193
includes taxes & fees
12 Aug - 13 Aug
Hilton Vacation Club The Historic Powhatan Williamsburg
Gaylord National Resort & Convention Center
Experience the serene ambiance of our hotel, surrounded by a beautifully maintained garden with a central water feature.

Gaylord National Resort & Convention Center

4.0 star property
8.8 out of 10, Excellent, (1006)
" Great hotel "
The price is AU$446
includes taxes & fees
1 Sept - 2 Sept
Gaylord National Resort & Convention Center
Great Wolf Lodge Williamsburg
Relax by the rectangular pool surrounded by hotel buildings with balconies.

Great Wolf Lodge Williamsburg

3.5 star property
8.6 out of 10, Excellent, (1003)
"Great place to enjoy with childrens"
The price is AU$315
includes taxes & fees
24 Aug - 25 Aug
Great Wolf Lodge Williamsburg
Hyatt Regency Chesapeake Bay
Relax by the resort's circular pool surrounded by lounge chairs and a covered seating area, with a dock and boats nearby.

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1000)
"Excellent place only missing the club room !!!"
The price is AU$440
includes taxes & fees
25 Aug - 26 Aug
Hyatt Regency Chesapeake Bay
Hilton Vacation Club Greensprings Williamsburg
Stunning two-story home with a brick and siding facade, featuring a central entrance and beautifully manicured lawn.

Hilton Vacation Club Greensprings Williamsburg

3.0 star property
8.4 out of 10, Very good, (1001)
"everything was great from check in to check out. "
The price is AU$215
includes taxes & fees
5 Aug - 6 Aug
Hilton Vacation Club Greensprings Williamsburg
MGM National Harbor Resort & Casino
Experience the sleek, curved design of this high-rise building, offering scenic views of the surrounding area.

MGM National Harbor Resort & Casino

4.5 star property
8.8 out of 10, Excellent, (1001)
"Quick and easy stay for a show. Everything you need is available within the resort. "
The price is AU$520
includes taxes & fees
25 Aug - 26 Aug
MGM National Harbor Resort & Casino
Club Wyndham Kingsgate
Relax by the pool surrounded by a pergola and enjoy a refreshing drink at the bar.

Club Wyndham Kingsgate

3.0 star property
8.8 out of 10, Excellent, (1001)
"Very nice spot to visit "
Club Wyndham Kingsgate
Holiday Inn Club Vacations Williamsburg Resort by IHG
Stately brick building with a central entrance and columns, situated near a serene water feature.

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 star property
9.0 out of 10, Wonderful, (478)
"Very well put together was very impressed with all they had me and my family will definitely be back."
The price is AU$199
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Club Vacations Williamsburg Resort by IHG
Discover the Perfect Family Getaway at Wyndham National Harbor – 2 Bedroom Dlx
Experience the grandeur of this hotel's central atrium, featuring a spacious open area with a clear view of the surrounding street.

Discover the Perfect Family Getaway at Wyndham National Harbor – 2 Bedroom Dlx

9.8 out of 10, Exceptional, (49)
"I loved the central location. The area around the property was great for dining, shopping, and is very walkable. "
Discover the Perfect Family Getaway at Wyndham National Harbor – 2 Bedroom Dlx
Spacious 3 Bedroom Lockoff, Full Kitchen, Near CW and W&M -Wyndham Kingsgate
Relax by the pool with a clear view of the adjacent gym area.

Spacious 3 Bedroom Lockoff, Full Kitchen, Near CW and W&M -Wyndham Kingsgate

2.0 star property
9.4 out of 10, Exceptional, (280)
"Amazing place great price too..we will return "
Spacious 3 Bedroom Lockoff, Full Kitchen, Near CW and W&M -Wyndham Kingsgate
Discover Family Fun and History at Wyndham Kingsgate-1 Bedroom Suite
Relax by the pool, surrounded by a spacious seating area and a view of the adjacent gym.

Discover Family Fun and History at Wyndham Kingsgate-1 Bedroom Suite

2.0 star property
9.2 out of 10, Wonderful, (62)
"A good place to stay to enjoy Williamsburg attractions."
Discover Family Fun and History at Wyndham Kingsgate-1 Bedroom Suite
Wyndham National Harbor 2-Bedroom Dlx with Balcony – Your Ultimate Family Escape
Experience the sleek, modern design of this hotel, featuring a symmetrical facade with balconies and a central entrance with poolside seating.

Wyndham National Harbor 2-Bedroom Dlx with Balcony – Your Ultimate Family Escape

Wyndham National Harbor 2-Bedroom Dlx with Balcony – Your Ultimate Family Escape
Family Friendly Countryside Resort Condos close to Colonial Williamsburg
Relax by the clear blue pool surrounded by lounge chairs and umbrellas.

Family Friendly Countryside Resort Condos close to Colonial Williamsburg

9.6 out of 10, Exceptional, (108)
"Clean, kid friendly, and accessible facility"
Family Friendly Countryside Resort Condos close to Colonial Williamsburg
Located Near Colonial Williamsburg, Busch Gardens, Jamestown-Wyn Kingsgate 2 Bd.
Relax by the pool surrounded by lounge chairs and tables, with a clear view through large windows.

Located Near Colonial Williamsburg, Busch Gardens, Jamestown-Wyn Kingsgate 2 Bd.

2.0 star property
9.4 out of 10, Exceptional, (199)
"A great place for families. Plenty to do onsite when not touring the historical areas. Clean, safe, and friendly staff. "
Located Near Colonial Williamsburg, Busch Gardens, Jamestown-Wyn Kingsgate 2 Bd.
Historic Charm Meets Modern Comfort at Wyndham Governor's Green Resort -2 Bd Dlx
Relax by the pool surrounded by lounge chairs and umbrellas.

Historic Charm Meets Modern Comfort at Wyndham Governor's Green Resort -2 Bd Dlx

2.0 star property
9.6 out of 10, Exceptional, (82)
"Quiet location, beautiful grounds and property was very clean"
Historic Charm Meets Modern Comfort at Wyndham Governor's Green Resort -2 Bd Dlx
Club Wyndham Patriots Place
Sports facility

Club Wyndham Patriots Place

2.5 star property
8.8 out of 10, Excellent, (3)
"I would recommend everyone go ahead and stay "
Club Wyndham Patriots Place
Greensprings Resort
Relax by the pool at this tranquil retreat, surrounded by lush greenery and a picturesque patio area.

Greensprings Resort

9.6 out of 10, Exceptional, (14)
"Nice place, great location. We would definitely stay again."
Greensprings Resort
2Bed/2Bath Cozy Deluxe Condo in Historic Williamsburg Kingsgate Resort!!
Relax by the pool in a covered seating area with comfortable chairs and a table.

2Bed/2Bath Cozy Deluxe Condo in Historic Williamsburg Kingsgate Resort!!

9.4 out of 10, Exceptional, (3)
"The first room we got checked into had fleas, but we contacted the front desk and they were able to put us into another newly renovated unit which was much nicer, had a better view and was very clean. The staff was very friendly and helpful and they compensated the issue with the room by waving the resort fees and giving us a gift card. "
2Bed/2Bath Cozy Deluxe Condo in Historic Williamsburg Kingsgate Resort!!
1BR 1BTH - Family of 4 - Resort Stay 5 min from Bush Gardens & Water Country USA
King's Creek features a charming two-story building with a gabled roof and a beautifully manicured lawn.

1BR 1BTH - Family of 4 - Resort Stay 5 min from Bush Gardens & Water Country USA

1BR 1BTH - Family of 4 - Resort Stay 5 min from Bush Gardens & Water Country USA
Lovely 2 bedroom minutes to Colonial Williamsburg
Relax by the pool surrounded by lounge chairs and umbrellas, with a shaded gazebo nearby.

Lovely 2 bedroom minutes to Colonial Williamsburg

9.6 out of 10, Exceptional, (4)
"We had a great stay and the condo was very comfortable for our family."
Lovely 2 bedroom minutes to Colonial Williamsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free