Search all holiday resorts in Chesapeake Bay

40 available resort offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chesapeake Bay resorts
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

40 Best resorts in Chesapeake Bay

Best Chesapeake Bay resorts with a jacuzzi

Among the 40 accommodations in Chesapeake Bay, here are the 4 best resorts with a jacuzzi

Hilton Virginia Beach Oceanfront - Chesapeake Bay
8.3 3650 reviews

Hilton Virginia Beach Oceanfront

resort, Virginia Beach
The Hilton Virginia Beach Oceanfront is situated directly on the Virginia Beach Oceanfront, just a short walk from the boardwalk and the Shoppes at 31. This hotel has consistently received very good ratings for cleanliness, user experience, and location.
The hotel offers a range of amenities, including a rooftop infinity pool, a sky bar, and a fitness centre. Guests can enjoy on-site dining at Catch 31 restaurant and take advantage of the complimentary shuttle service to nearby attractions.
Club Wyndham Kingsgate - Chesapeake Bay
8.9 4325 reviews

Club Wyndham Kingsgate

resort, Williamsburg
Club Wyndham Kingsgate is located in Williamsburg, less than a kilometre from the historic area, making it a great base for exploring the town's rich history. This 3-star hotel has consistently received very good user ratings, suggesting a comfortable and enjoyable stay.
The hotel offers a range of amenities and activities, including a swimming pool, jacuzzi, and tennis court, making it suitable for families and those seeking relaxation. Guests can also enjoy a restaurant, bar, and fitness centre, ensuring a convenient and enjoyable stay.
Hyatt Regency Chesapeake Bay - Chesapeake Bay
No reviews

Hyatt Regency Chesapeake Bay

resort, Cambridge
The Hyatt Regency Chesapeake Bay is a short distance from Cambridge city centre, offering a peaceful retreat from the bustle of the town. It's a great option for those who want to be close to the action but also enjoy some quiet time.
This hotel has a range of facilities for all ages, including an outdoor pool, a spa, a fitness centre, and a restaurant. There's also a children's play area, making it ideal for families.
Westgate Historic Williamsburg Resort - Chesapeake Bay
8.6 1788 reviews

Westgate Historic Williamsburg Resort

resort, Williamsburg
The Westgate Historic Williamsburg Resort is conveniently located in Williamsburg, Virginia, just a short distance from Busch Gardens and the historic district. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodation options, from comfortable rooms to spacious suites, all with modern amenities. Guests can enjoy a variety of facilities, including a swimming pool, fitness centre, tennis court, and a restaurant and bar.

Best Chesapeake Bay resorts with a pool

Among the 40 accommodations in Chesapeake Bay, here are the 4 best resorts with a pool

Gated Williamsburg Stay  Spacious Townhome Near Jamestowne & Parks - Chesapeake Bay
No reviews

Gated Williamsburg Stay Spacious Townhome Near Jamestowne & Parks

resort, Williamsburg
The "Gated Williamsburg Stay" offers spacious townhome accommodation in Williamsburg, a short drive from Busch Gardens, Colonial Williamsburg, and Newport News/Williamsburg Airport, with convenient access to Water Country USA and Historic Jamestowne.
These family-friendly luxury accommodations provide 46.5 square meters of living space, featuring two bedrooms and two bathrooms to sleep up to six guests, complete with a kitchen, 50-inch television with premium cable, daily cleaning, on-site tennis and miniature golf, saunas, a fitness centre, and an outdoor shared swimming pool, with complimentary parking included.
Hilton Vacation Club The Historic Powhatan Williamsburg - Chesapeake Bay
9.1 6051 reviews

Hilton Vacation Club The Historic Powhatan Williamsburg

resort, Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg is located just outside of Historic Williamsburg, a short drive from the historic district and close to other attractions like WakeMed Soccer Park and the College of William and Mary. This resort has received very good user ratings, with excellent scores for location and cleanliness.
The resort offers spacious suites on the grounds of a restored Manor House, providing a unique and historic ambiance. Guests can enjoy a range of amenities and activities, including a swimming pool, a jacuzzi, a tennis court, and a fitness centre, as well as on-site dining options and a children's playground.
Peaceful 1br Retreat In Gated Estate Near History + Local Parks - Chesapeake Bay
No reviews

Peaceful 1br Retreat In Gated Estate Near History + Local Parks

resort, Williamsburg
The "Peaceful 1br Retreat In Gated Estate Near History + Local Parks" holiday apartment is located in Williamsburg, a short drive from Busch Gardens Williamsburg and Colonial Williamsburg, and approximately 10 kilometres from Newport News/Williamsburg Airport, with convenient access to Water Country USA and Historic Jamestowne.
This 56 square metre, one-bedroom, two-bathroom holiday apartment accommodates up to four guests and offers amenities such as air conditioning, a kitchen, a 50-inch television, complimentary toiletries, daily cleaning, a fitness centre, a shared outdoor swimming pool, tennis, and miniature golf.
Delta Hotels By Marriott™ Virginia Beach Waterfront Suites - Chesapeake Bay
8.5 5153 reviews

Delta Hotels By Marriott™ Virginia Beach Waterfront Suites

resort, Virginia Beach
The Delta Hotels by Marriott Virginia Beach Waterfront is situated on the Chesapeake Bay, a short distance from Seashore State Park and 9.6 miles from the Virginia Marine Science Museum. This resort has received very good ratings for location, cleanliness, and overall user experience.
The hotel offers spacious guest rooms with separate sleeping and living areas, perfect for families or groups. Guests can enjoy a variety of amenities, including a private beach, an outdoor pool, a fitness centre, and a restaurant and bar.

Frequently asked questions about resorts in Chesapeake Bay

  • What are the top attractions in Baie de Chesapeake?

    Chesapeake Bay has so much to offer! You've got the historic Annapolis, the charming town of St. Michaels, and the beautiful Assateague Island National Seashore, where you can see wild horses roaming free. Of course, you can't forget about the Chesapeake Bay Bridge, a real icon of the area.
  • What are the best resorts with a swimming pool in Chesapeake Bay?

    Top Rated Family Resort Destination - 4bdr Lock-off From Only $379, Club Wyndham Governors Green and Patriots Inn are among the best resorts with a swimming pool in Chesapeake Bay.

  • Which area in Baie de Chesapeake is good for staying in a resort?

    Ocean City is the place to be for a resort stay. It's a popular holiday destination with plenty of hotels and resorts to choose from, offering everything from swimming pools and water parks to spas and golf courses. You've also got plenty of restaurants and shops to explore.
  • What are the best resorts with jacuzzi in Chesapeake Bay?

  • What time of the year is the best to stay in a resort Baie de Chesapeake?

    Summer is definitely the most popular time to visit, with warm weather perfect for swimming and sunbathing. But if you're looking for a quieter experience, spring or autumn can be great too, with mild temperatures and beautiful foliage.
  • What are the best family friendly resorts in Chesapeake Bay?

  • How easy is it to get to Baie de Chesapeake?

    It's really easy to get to Chesapeake Bay. You can fly into Baltimore-Washington International Airport (BWI) and then drive down, or you can drive straight there from major cities on the East Coast. There are also ferries that run to some of the islands in the bay, making it easy to explore different parts of the region.
  • What are the best pet friendly resorts in Chesapeake Bay?

  • Where are the best markets in Baie de Chesapeake?

    The Easton Farmers' Market is a must-visit for fresh produce, local crafts and delicious food. If you're looking for something more unique, the Chesapeake Bay Maritime Museum in St. Michaels has a fantastic market with handmade crafts and local goods.
  • What are the best sports events or competitions happening in and around Baie de Chesapeake?

    The Bay Bridge Run is a popular annual event, with runners crossing the Chesapeake Bay Bridge. If you're into sailing, the Annapolis Boat Show is a great event to check out. And for something a bit more unique, the National Hard Crab Derby in Crisfield is a fun and quirky event.
  • What are the most requested amenities in resorts in Baie de Chesapeake?

    Most resorts offer swimming pools, hot tubs, and fitness centres. Many also have restaurants and bars on-site, as well as activities like kayaking, paddleboarding, and fishing. Some even have private beaches or marinas.
  • What are the most romantic attractions in Baie de Chesapeake's?

    A sunset cruise on the bay is always a winner for a romantic evening. Or you could take a stroll along the boardwalk in Ocean City, hand-in-hand, watching the waves roll in. For something a bit more unique, try a romantic dinner at The Chart House in Annapolis, with stunning views over the water.

Popular destinations

Best Chesapeake Bay resorts with air conditioning

Aqua Vista Resort Hotel - Chesapeake Bay
No reviews

Aqua Vista Resort Hotel

resort, Virginia Beach
Aqua Vista Resort Hotel in Virginia Beach offers convenient accommodation within walking distance of the city centre and close to Seabreeze Beach, 17th Street Park, and Atlantic Fun Park.
The hotel features free Wi-Fi, an outdoor pool, children's playrooms, a fitness centre, and on-site parking; guests can also utilise the lift and ATM.
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina - Chesapeake Bay
8.7 1460 reviews

Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina

resort, Cambridge
The Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is situated in Cambridge, Maryland, just a short drive from the Cambridge - Dorchester Regional Airport and offering easy access to the beautiful Chesapeake Bay. The resort has consistently received very good ratings for its location, cleanliness and overall experience.
The hotel features a range of facilities including a championship golf course, a full-service spa and salon, a marina with 150 slips, three restaurants, three swimming pools, a fitness centre and tennis courts. Guests can also enjoy a variety of activities such as boating, fishing, swimming and spa treatments.
Holiday Inn Express Annapolis East-kent Island By Ihg - Chesapeake Bay
9.2 1256 reviews

Holiday Inn Express Annapolis East-kent Island By Ihg

resort, Kent Narrows
The Holiday Inn Express Annapolis East-Kent Island is situated in Grasonville, just 20 miles from Annapolis Harbor and 30 miles from Baltimore-Washington International Airport, offering easy access to both bustling city life and the tranquil beauty of Kent Narrows. The hotel has received very good user ratings for cleanliness and an excellent rating for its location.
The hotel features 25 square metre rooms with one bedroom and one bathroom, each with a range of modern amenities. Guests can enjoy a variety of activities, including swimming in the seasonal outdoor pool, relaxing in the garden, and dining at the on-site restaurant and bar, as well as taking advantage of the fitness centre and tennis court.
The Colony At Virginia Beach - Chesapeake Bay
8.6 53 reviews

The Colony At Virginia Beach

resort, Virginia Beach
The Colony at Virginia Beach is situated steps from Virginia Beach itself, a short distance from the Virginia Beach Fishing Pier and approximately 2.4 kilometres from the King Neptune Statue.
This 1240-square-metre property offers 11 guests a self-catering holiday home with a swimming pool, terrace, free parking, and rooms featuring refrigerators and sea views; it does not accommodate stag or hen parties.

Best Chesapeake Bay resorts with a gym

Holiday Inn Express Williamsburg North By Ihg - Chesapeake Bay
9.0 2285 reviews

Holiday Inn Express Williamsburg North By Ihg

resort, Williamsburg
The Holiday Inn Express Williamsburg North is conveniently located just 15 minutes from Busch Gardens and within 10 miles of the College of William and Mary, making it a great base for exploring Williamsburg's historical attractions and entertainment. The hotel consistently receives very good ratings for location, cleanliness, and overall experience.
The hotel offers a range of amenities, including a fitness centre, indoor pool, and complimentary continental breakfast. Guests can also enjoy comfortable rooms with cable TV, free toiletries, and select rooms with sofa beds, as well as a suite with a spa tub.
2br Cottage W/ Modern Kitchen, Outdoor Dining & Washer/dryer Access | 2 Units - Chesapeake Bay
No reviews

2br Cottage W/ Modern Kitchen, Outdoor Dining & Washer/dryer Access | 2 Units

resort, Williamsburg
This resort in Williamsburg offers the "2br Cottage W/ Modern Kitchen, Outdoor Dining & Washer/dryer Access | 2 Units" and is conveniently located a short drive from Busch Gardens, Colonial Williamsburg, Water Country USA, and Historic Jamestowne.
This accommodation provides family-friendly luxury with four bedrooms and four bathrooms, accommodating up to 12 guests, and features on-site tennis, miniature golf, a fitness centre, and a shared outdoor pool, with rooms measuring approximately 46 square metres.
Premium Escape W/ Garden Tub & Deck In Williamsburg Gated Community | 4 Units - Chesapeake Bay
No reviews

Premium Escape W/ Garden Tub & Deck In Williamsburg Gated Community | 4 Units

resort, Williamsburg
The Premium Escape W/ Garden Tub & Deck In Williamsburg Gated Community | 4 Units is located in Williamsburg, a short drive from major attractions such as Busch Gardens, Colonial Williamsburg, and Water Country USA, with convenient access to Newport News/Williamsburg Airport.
This resort offers family-friendly luxury accommodation with 4 bedrooms and 4 bathrooms, accommodating up to 16 guests, and features on-site recreational activities including tennis and miniature golf, alongside a shared outdoor swimming pool and fitness centre.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.0 2797 reviews

The Atrium Resort, Virginia Beach By Vacatia

resort, Virginia Beach
The Atrium Resort by VSA Resorts is located directly on the Virginia Beach Boardwalk, just a short walk from the beach and a couple of minutes' drive from attractions like Jungle Golf and the Old Coast Guard Station Museum. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a range of facilities, including a swimming pool, hot tub, fitness centre, and free Wi-Fi.
©2026 cozycozy.com