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

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 2973 reviews

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

resort, Virginia Beach
Ocean Sands Resort by VSA Resorts is situated on the oceanfront in Virginia Beach, just half a mile from the amusement park and one mile from the convention centre. The resort consistently receives excellent ratings for its location and cleanliness, as well as very good reviews for its overall experience.
The resort offers a range of self-catering suites with Caribbean-style decor, each with a private balcony or terrace. Guests have access to a variety of on-site amenities, including a swimming pool, hot tub, sauna, fitness centre, tennis court, restaurant, bar, and spa, ensuring a relaxing and enjoyable stay.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.1 2726 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.
Westgate Historic Williamsburg Resort - Chesapeake Bay
8.7 1789 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.
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.

Best Chesapeake Bay resorts with a pool

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

Stylish Estate Stay Just Minutes From Museums, Dining & Attractions - Chesapeake Bay
No reviews

Stylish Estate Stay Just Minutes From Museums, Dining & Attractions

resort, Williamsburg
The "Stylish Estate Stay Just Minutes From Museums, Dining & Attractions" resort in Williamsburg offers a convenient base, located a short distance from Busch Gardens, Colonial Williamsburg, and Water Country USA, with easy access to Newport News/Williamsburg Airport.
This 1-bedroom, 2-bathroom suite accommodates up to 4 guests, featuring a 58-square-metre living space with a kitchen, complimentary toiletries, and daily cleaning, alongside access to an outdoor shared swimming pool, fitness centre, tennis, and miniature golf facilities.
Hilton Vacation Club Greensprings Williamsburg - Chesapeake Bay
8.9 3911 reviews

Hilton Vacation Club Greensprings Williamsburg

resort, Williamsburg
Greensprings Vacation Resort is located near the Green Springs National Historic Landmark District in Williamsburg, providing easy access to the area's rich history and top attractions. The resort has consistently received very good ratings for its cleanliness and user experience, with an excellent location rating.
The resort offers spacious apartments with fully equipped kitchens and comfortable fireplaces, providing a home-away-from-home feel. Guests can enjoy amenities such as a swimming pool, jacuzzi, fitness centre, tennis court, and a restaurant and bar, ensuring a relaxing and enjoyable stay.
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina - Chesapeake Bay
8.7 1443 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.
Club Wyndham Kingsgate - Chesapeake Bay
8.9 4309 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.

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

Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony - Chesapeake Bay
10 2 reviews

Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony

resort, Virginia Beach
Barclay Towers Resort, situated in the Northeast Virginia Beach district directly on the Virginia Beach Boardwalk, offers oceanfront accommodation with easy access to the beach and attractions such as the Veterans United Home Loans Amphitheatre.
The Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony features a one-bedroom suite sleeping up to four guests, complete with a fully equipped kitchen, an indoor pool, hot tub, fitness centre, and free parking across the street.
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.
Relax In A Private Escape W/ Jetted Tub & Garden Deck - Chesapeake Bay
7.6 4 reviews

Relax In A Private Escape W/ Jetted Tub & Garden Deck

resort, Williamsburg
This resort in Williamsburg offers a private escape with a whirlpool tub and garden deck, located just minutes from Busch Gardens and Colonial Williamsburg, with convenient access to Water Country USA and Historic Jamestowne, and a short drive from Newport News/Williamsburg Airport.
Each 45 square metre accommodation is equipped with a kitchen, 50-inch television with Premium cable, and complimentary toiletries, and guests can enjoy on-site recreational activities including tennis and miniature golf, alongside a shared outdoor swimming pool and saunas, with daily housekeeping and flexible check-in from 4:00 pm.
Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay At Sandy Cove - Chesapeake Bay
9.6 9 reviews

Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay At Sandy Cove

resort, Charlestown
This charming cabin is located just 15km from Elk Neck State Park, Upper Bay Museum, and Milburn Stone Theater, offering easy access to a range of attractions and activities. The property has consistently received excellent reviews from previous guests.
The comfortable lodge is ideal for families or groups, with 2 bedrooms, 1 bathroom and a 37 square meter floor area, accommodating up to 8 guests. Enjoy a relaxing stay with amenities including an indoor and outdoor pool, a fitness centre, a tennis court, a garden, and a winery attached to the property.

Best Chesapeake Bay resorts with a gym

Upscale Gated Retreat W/ Plush Bed & Garden Views Minutes From Jamestown - Chesapeake Bay
No reviews

Upscale Gated Retreat W/ Plush Bed & Garden Views Minutes From Jamestown

resort, Williamsburg
This resort in Williamsburg offers the "Upscale Gated Retreat W/ Plush Bed & Garden Views Minutes From Jamestown" and is located a short drive from Newport News/Williamsburg Airport, providing convenient access to Busch Gardens and Colonial Williamsburg.
This 43.7 square metre accommodation sleeps up to four guests and features two bedrooms, one bathroom, air conditioning, a swimming pool, a garden, a fitness centre, and complimentary daily cleaning services.
Delta Hotels By Marriott™ Virginia Beach Waterfront Suites - Chesapeake Bay
8.5 5156 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.
Two Stay: High-end Cottages Near Trails, Museums & Colonial District Attractions - Chesapeake Bay
No reviews

Two Stay: High-end Cottages Near Trails, Museums & Colonial District Attractions

resort, Williamsburg
This resort, offering high-end cottages, is located in Williamsburg, providing easy access to Busch Gardens, Colonial Williamsburg, and Water Country USA, with the Newport News/Williamsburg Airport approximately 35 kilometres away.
These spacious 43 square metre, two-bedroom, two-bathroom cottages accommodate up to eight guests and feature kitchens, 50-inch televisions, air conditioning, complimentary toiletries, daily cleaning, a shared outdoor swimming pool, a fitness centre, tennis, miniature golf, and on-site saunas, with complimentary parking available.
3 Premium 2br Cottages Near Jamestowne, Museums & Family Attractions - Chesapeake Bay
No reviews

3 Premium 2br Cottages Near Jamestowne, Museums & Family Attractions

resort, Williamsburg
The "3 Premium 2br Cottages Near Jamestowne, Museums & Family Attractions" lodging is situated in Williamsburg, a short drive from Newport News/Williamsburg Airport, placing guests within easy reach of Busch Gardens, Colonial Williamsburg, and Water Country USA.
This resort offers spacious 500 sq. ft. cottages with kitchens, air conditioning, a shared swimming pool, fitness centre, and on-site activities including tennis and miniature golf, accommodating up to 18 guests.
©2026 cozycozy.com