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Best Vacation rentals and Airbnb offers in Chesapeake Bay
10 182 reviews
Chesapeake Bay
08/29 – 09/05
$198/nighttotal: $1386 (7 )
Summer Escape - Dock, Pool, Firepits, & Kayaks
1 2
house , Gloucester Courthouse
This Gloucester Courthouse guesthouse, situated on 10 acres near Bland Creek, offers easy access to Gloucester's shops and restaurants (15 minutes), Yorktown's Riverwalk (30 minutes), and Williamsburg's historical attractions (45 minutes). This 800-square-foot apartment features two bedrooms, one bathroom, and accommodates four guests, boasting a screened porch, saltwater pool (seasonal), private chiminea, and access to a shared dock for fishing and kayaking on Bland Creek.
Chesapeake Bay
07/30 – 08/05
$259/nighttotal: $1554 (6 )
3 Mi To Washington College! Updated Home W/ Patio
3 6
house , Kingstown
This vacation home in Kingstown is located 48 miles from New Castle Airport. This 1000 square foot house accommodates up to 7 guests with 3 bedrooms, 1 bathroom, a fully equipped kitchen, air conditioning, and a garden, offering complimentary WiFi and private parking.
This historic waterman's cottage offers a unique waterside retreat in Rock Hall, situated within a 1-minute walk to downtown amenities and a 3-minute walk to beaches and marinas. This 1-bedroom, 1-bathroom apartment accommodates up to 2 guests and features a fully equipped kitchen, 250 Mbps WiFi, a screened-in porch, onsite laundry, and access to exercise equipment.
9.8 390 reviews
Chesapeake Bay
08/23 – 08/28
$153/nighttotal: $765 (5 )
The Moore Cottage
1 2
apartment , White Stone
The Moore Cottage is located on the Northern Neck, just a mile from Windmill Point Marina and five miles from the town of White Stone, offering a peaceful and secluded getaway. The cottage has received excellent ratings for its location, cleanliness, and overall experience. The cottage features one bedroom and one bathroom, comfortably accommodating up to two guests. The property includes a private back porch with stunning views, a propane grill, two kayaks, and a paddleboard for exploring the surrounding waters.
9.8 71 reviews
Chesapeake Bay
06/27 – 07/04
$223/nighttotal: $1561 (7 )
Artistic Environment Inspiring Home
3 3
apartment , Kilmarnock
This 3-bedroom accommodation is located in Balls Neck, within 2 miles of 2 state parks at the Chesapeake Bay and 8 miles from Kilmarnock. With excellent user, location, and cleanliness ratings, this spacious 3-bedroom house is situated on 9 acres with double panoramic decks, offering stunning views of the surrounding area and wildlife. With over 1,800 sq. ft., the house features 3 bedrooms, 2 bathrooms, a fully equipped kitchen, a dining area, and a family room with a TV and DVD player. Guests have access to 9.5 acres of land for walking, as well as a neighboring 36-acre park in progress. The area is known for its great fishing, with charter boats available for half-day and full-day trips.
10 1 review
Chesapeake Bay
08/29 – 09/05
$190/nighttotal: $1330 (7 )
Baltimore Home < 2 Mi To Dtwn Towson
1 2
house , Baltimore
This charming Baltimore vacation rental is located in Towson, just a short distance from downtown Towson, the Baltimore Museum of Art, and Clifton Park. It's a convenient spot for exploring the city and its surrounding attractions. The 1-bedroom house offers 650 square feet of space and accommodates up to 2 guests. It features a fully equipped kitchen, a washing machine, a flat-screen TV, free Wi-Fi, and a relaxing atmosphere for a comfortable stay.
10 29 reviews
Chesapeake Bay
07/30 – 08/05
$405/nighttotal: $2430 (6 )
A Little Slice Of Heaven On The Choptank River.
2 6
chalet , Cambridge
This charming cottage is located in East New Market, just across from the Hyatt Resort and a short distance from downtown Cambridge's attractions and restaurants. The chalet has received excellent user ratings, making it a popular choice for travelers. The cottage features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy access to a private waterfront location with a terrace, a garden, and a kitchen equipped with a fridge and microwave, plus amenities like air conditioning.
9.8 7 reviews
Chesapeake Bay
08/29 – 09/05
$218/nighttotal: $1526 (7 )
Walk To Beach: Pet-friendly Gem In Scotland!
1 2
cottage , Piney Point
This Piney Point cottage, near Point Lookout State Park (1 mile), Buzz's and Drury's marinas (4 miles), and Piney Point Lighthouse (27 miles), offers a convenient location for exploring the Chesapeake Bay area. This 420-square-foot vacation home features one bedroom, one bathroom, sleeps three guests, includes a full kitchen, washer/dryer, and a sunroom, plus a furnished deck with a charcoal grill; one pet is allowed for a fee.
9.8 28 reviews
Chesapeake Bay
07/30 – 08/05
$215/nighttotal: $1290 (6 )
Bubba Butler's Cottage
3 6
cottage , Urbanna
This Locust Hill cottage, near the Middlesex County Museum, Piankatank River Golf Club, and Urbanna Historic District (all within 9 miles), offers easy access to White Stone Beach (11.6 miles away). This three-bedroom, two-bathroom vacation home sleeps six and includes amenities such as a washer, dryer, and air conditioning, making it perfect for families or groups exploring Urbanna and its surrounding attractions.
9.0 2280 reviews
Chesapeake Bay
08/23 – 08/28
$121/nighttotal: $605 (5 )
Holiday Inn Express Williamsburg North By Ihg
1 2
resort , Williamsburg
The Holiday Inn Express Williamsburg North is located just outside the historic district, making it easy to reach Busch Gardens in 15 minutes and the College of William and Mary in 10 miles. This hotel consistently receives very good ratings for location, cleanliness, and overall user experience. The hotel offers a range of amenities, including a fitness center, indoor pool, and continental breakfast. Guests can also enjoy comfortable rooms, some with sofa beds, and select suites with spa tubs.
9.8 54 reviews
Chesapeake Bay
08/23 – 08/28
$211/nighttotal: $1055 (5 )
Shadowlawn Villas, Suite Ii
1 2
apartment , Virginia Beach
This apartment is located in Northeast Virginia Beach, just a short walk from Pacific Avenue and the Virginia Beach Boardwalk, providing easy access to the beach and local attractions. The apartment has received excellent ratings for location, cleanliness, and overall experience, making it a great choice for travelers. The apartment has one bedroom and one bathroom, comfortably accommodating two guests. It features a fully equipped kitchen, a terrace or balcony, and access to a swimming pool, spa, and parking, ensuring a relaxing and enjoyable stay.
9.5 2 reviews
Chesapeake Bay
06/27 – 07/04
$187/nighttotal: $1309 (7 )
Downtown And Inner Harbor Apartment
1 3
apartment , Baltimore
This downtown Baltimore rental unit is located within a mile of the University of Maryland - Baltimore, Sports Legends Museum at Camden Yards, and Carroll Park, offering easy access to the Inner Harbor and Baltimore Convention Center. This 570 square foot, one-bedroom condo accommodates up to 5 guests and features a fully equipped kitchen, free WiFi, free private parking, and a washing machine.
Best Chesapeake Bay vacation rentals with a balcony
Chesapeake Bay
07/30 – 08/05
$384/nighttotal: $2304 (6 )
< 1 Mi To Boat Ramp: Coastal Virginia Hideaway
3 6
house , Exmore
This coastal Virginia house is located in Exmore, less than 5280 feet from a boat ramp and 54 miles from Norfolk International Airport. This 1500 square foot home accommodates up to 11 guests with 3 bedrooms, 2 bathrooms, air conditioning, complimentary Wi-Fi, a well-equipped kitchen, and a patio with sea views.
9.1 1605 reviews
Chesapeake Bay
08/23 – 08/28
$151/nighttotal: $755 (5 )
Holiday Inn Express Annapolis East-kent Island By Ihg
1 2
resort , Kent Narrows
The Holiday Inn Express Annapolis East-Kent Island is located in Grasonville, just a short drive from the charming town of Kent Narrows and its waterfront restaurants, as well as the historical attractions of Annapolis Harbor. This hotel has received very good user ratings, excellent location ratings, and very good cleanliness ratings. The hotel has 270 square foot rooms with one bedroom and one bathroom. Guests can enjoy amenities such as a swimming pool, tennis court, fitness center, restaurant, bar, and free parking.
8.0 7626 reviews
Chesapeake Bay
08/23 – 08/28
$210/nighttotal: $1050 (5 )
The Barclay Towers Hotel And Resort
1 2
resort , Virginia Beach
The Barclay Towers Resort Hotel in Northeast Virginia Beach boasts a direct boardwalk location, within a 10-minute walk of the Virginia Beach Boardwalk, Atlantic Wildfowl Heritage Museum, and Virginia Beach Fishing Pier. This family-friendly hotel offers a fitness center, hot tub, and on-site restaurant and bar, providing convenient access to attractions and amenities.
9.8 315 reviews
Chesapeake Bay
08/23 – 08/28
$171/nighttotal: $855 (5 )
The Heron's Nest At Atlantic Marina
1 2
cottage , Lake Shore
This charming cottage is located in Pasadena, just steps from the beach on the Patapsco River, offering breathtaking water views and a peaceful escape. The cottage has consistently received excellent reviews from previous guests. The cottage has a spacious layout with 580 square feet of living space, one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a private porch, and access to a swimming pool, making it perfect for families and groups seeking a relaxing getaway.
Search Family Vacation Rentals in Chesapeake Bay
These family-friendly vacation rentals in Chesapeake Bay offer plenty of room to spread out near local beaches.
9.0 47 reviews
Chesapeake Bay
08/23 – 08/28
$124/nighttotal: $620 (5 )
* Private Suite Full Of Style & Comfort *
1 2
apartment , Lutherville
This apartment is perfect for travelers visiting Lutherville. It is located in the heart of Lutherville Timonium, within a 3-mile radius of Goucher College, Towson Town Center, and Towson University. The apartment has received excellent user ratings and can accommodate up to 4 guests with 1 bedroom and 1 bathroom. The apartment features a fully equipped kitchen, a comfortable living space with a sofa bed, a Smart TV with a DVD player, a washing machine, and access to a garden. It is also pet-friendly and offers parking.
9.6 53 reviews
Chesapeake Bay
06/27 – 07/04
$252/nighttotal: $1764 (7 )
"Heron's Nest" Charming Tiny House On Chesapeake Bay-boat Launch/slip Included
1 3
apartment , Kilmarnock
This waterfront apartment is located in Heathsville, a short drive from Kilmarnock, offering a peaceful escape on the Chesapeake Bay. It has received excellent user ratings for its comfortable accommodations and prime location. This rental features one bathroom, a 380 square foot floor area, and comfortably sleeps four guests. Enjoy amenities like a private terrace, a Jacuzzi, and a garden, as well as access to a deep-water ramp for launching small watercraft.
9.0 8 reviews
Chesapeake Bay
07/30 – 08/05
$242/nighttotal: $1452 (6 )
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.
1 6
cottage , Benedict
This Benedict, Maryland beach house boasts a unique beachfront location with over 500 feet of private beach and a 400-foot pier, near the Dr. Samuel A. Mudd House Museum and Drum Point Lighthouse. This one-bedroom, one-bathroom vacation rental sleeps six, featuring a queen bed, bunk beds, a sleeper sofa, a full kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, and a gas grill; enjoy nearby Walter's Walk sandbar for sunset viewing.
10 2 reviews
Chesapeake Bay
07/30 – 08/05
$370/nighttotal: $2220 (6 )
The Charming Cozy 4-bedroom Getaway In Glen Burnie
4 6
house , Glen Burnie
This recently renovated vacation home is located in Glen Burnie, Maryland, offering convenient access to the community's amenities. This 1260 square foot house features 4 bedrooms, 2 bathrooms, and can accommodate up to 8 guests, with amenities including complimentary Wi-Fi, private parking, air conditioning, and a kitchen equipped with a fridge and microwave oven.
Frequently Asked Questions about vacation rentals in Chesapeake Bay
Which neighborhood in Baie de Chesapeake should you consider for a vacation rental?
If you're looking for a charming and historic area, consider staying in Annapolis. It's the state capital of Maryland and has a lot to offer, including great restaurants, shops, and attractions. You can also find some beautiful waterfront vacation rentals in Annapolis.
What are the best Airbnb and vacation rentals in Chesapeake Bay?
What are the top family-friendly attractions in Baie de Chesapeake?
The Maryland Science Center in Baltimore is a great place for kids of all ages. They have interactive exhibits, a planetarium, and an IMAX theater. Also, the National Aquarium in Baltimore is a must-see, with a variety of marine life, including sharks, dolphins, and sea turtles.
What are the most popular Airbnbs in Chesapeake Bay?
When is the best time to book a vacation rental in Baie de Chesapeake?
The best time to book a vacation rental in Chesapeake Bay is in the spring or fall. The weather is mild and the crowds are smaller. If you're looking for a beach vacation, you might want to book in the summer, but be prepared for higher prices and more crowds.
What are the best vacation rentals with a pool in Chesapeake Bay?
What events or festivals should visitors check out in and around Baie de Chesapeake?
The Annapolis Maritime Museum hosts the annual Annapolis Boat Show in October. It's a great place to see all kinds of boats and talk to experts about boating. Also, the Chesapeake Bay Wine Festival in Stevensville is a great event to enjoy the local wines.
What are the best rentals for families and kids in Chesapeake Bay?
What are the best budget-friendly activities in Baie de Chesapeake?
You can enjoy a beautiful walk or bike ride along the Bay Trail, which runs for miles along the shores of the Chesapeake Bay. You can also visit one of the many state parks in the area, like Sandy Point State Park, which offers hiking, fishing, and camping.
What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?
What are the best restaurants with local dishes in Baie de Chesapeake?
Try the Chesapeake Inn in Stevensville for their famous crab cakes. They're made with fresh, local crab meat and are a true taste of the Chesapeake Bay. You can also check out the Blackwall Hitch in Annapolis, which has a great selection of seafood and other Chesapeake Bay dishes.
What are the best walking or cycling routes in Baie de Chesapeake?
The Bay Trail is a great option for walking or cycling. It runs for over 300 miles along the shores of the Chesapeake Bay, offering beautiful views and a chance to experience the natural beauty of the area. You can also find some great walking and cycling routes in the state parks, like Sandy Point State Park.
Are there pet-friendly attractions in Baie de Chesapeake?
Many of the state parks in the area are pet-friendly, like Sandy Point State Park. You can also find many pet-friendly restaurants and shops in the area. Just be sure to check with individual businesses to see if they allow pets.
What are the benefits of choosing a vacation rental in Baie de Chesapeake?
Vacation rentals offer more space and privacy than a hotel, and you can often find rentals that are pet-friendly. You can also find rentals in a variety of locations, from waterfront properties to those in the heart of town.
Destinations nearby
Best Chesapeake Bay vacation rentals with parking
9.6 49 reviews
Chesapeake Bay
08/29 – 09/05
$185/nighttotal: $1295 (7 )
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.
1 2
cottage , Shady Side
This Shady Side waterfront cottage sits on a peninsula on the West River, a short drive from Annapolis and close to Galesville, offering private dock access for boating and kayaking. The one-bedroom, one-bathroom home sleeps three, features a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and internet access; nearby attractions include Thanksgiving Farm Wines and South River Golf Links.
9.0 5809 reviews
Chesapeake Bay
10/01 – 10/05
$153/nighttotal: $612 (4 )
Hilton Vacation Club The Historic Powhatan Williamsburg
1 3
resort , Williamsburg
The Hilton Vacation Club The Historic Powhatan Williamsburg is located just a short drive from Historic Williamsburg and the College of William and Mary, offering easy access to the area's rich history and attractions. This resort consistently receives high ratings for its location, cleanliness, and overall experience. The resort features a restored Manor House setting, providing a unique historical ambiance. Guests can enjoy a range of amenities, including indoor and outdoor pools, tennis courts, a fitness center, and a variety of dining options, making it a perfect choice for families and couples alike.
9.7 177 reviews
Chesapeake Bay
10/01 – 10/05
$203/nighttotal: $812 (4 )
Cozy Home Away From Home Just Minutes From The Beach
1 3
apartment , Virginia Beach
This one-bedroom apartment is located just a 5-minute walk from Pacific Avenue and the Virginia Beach Boardwalk, putting you right in the heart of the action. Guests consistently rate the location, cleanliness, and overall experience as excellent. The 500-square-foot apartment comfortably accommodates up to 4 guests. Enjoy amenities like a fully equipped kitchen, a swimming pool, a spa, and a water park, all while being just a short walk from the beach and public transportation.
9.8 61 reviews
Chesapeake Bay
08/29 – 09/05
$225/nighttotal: $1575 (7 )
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay\n\n\n\n\n\n\n\n
2 2
cottage , Cecilton
This two-bedroom, one-bathroom cottage is located in Cecilton, just a short drive from the beach. It has an excellent user rating and can accommodate up to six guests. The cottage has a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking. The cottage is also pet-friendly and family-friendly, and it has free WiFi. It is situated near the beach and has a garden with barbecue grills. The cottage is within 16 miles of Bohemia Vista Marina and Crow Farm and Vineyard, and within 20 miles of C and D Canal Museum and Back Creek Golf Club.
Check Out Vacation Rentals with a Pool in Chesapeake Bay
A vacation rental with a pool in Chesapeake Bay is the ideal way to complement your daily coastal adventures.
8.8 10416 reviews
Chesapeake Bay
08/23 – 08/28
$87/nighttotal: $435 (5 )
Vacation Village At Williamsburg
1 2
resort , Williamsburg
Vacation Village at Williamsburg is located just minutes from Jamestown, six miles from Colonial Williamsburg, and five miles from the College of William and Mary, making it a convenient base for exploring the region's rich history and attractions. The resort consistently receives very good ratings for its cleanliness and overall experience, with an excellent location rating. The resort offers a range of comfortable apartments and suites, ideal for families or groups. Guests can enjoy amenities like swimming pools, a fitness center, a spa, and a tennis court, ensuring a relaxing and enjoyable stay.
10 2 reviews
Chesapeake Bay
08/29 – 09/05
$439/nighttotal: $3073 (7 )
Hampton Condo: By Convention Center & Coliseum!
2 2
house , Hampton
This Hampton condo is conveniently located near the Virginia Living Museum, just 10 miles from the airport, making it an ideal choice for travelers exploring the area. The apartment consistently receives excellent ratings for cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. This two-bedroom, three-bathroom rental offers 1800 square feet of space, comfortably accommodating up to four guests. Enjoy amenities like a swimming pool, fitness center, and a fully equipped kitchen with a dishwasher, along with a patio for relaxing and a garden for enjoying the fresh air.
9.8 64 reviews
Chesapeake Bay
10/01 – 10/05
$262/nighttotal: $1048 (4 )
Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony
1 3
apartment , Virginia Beach
This Virginia Beach apartment is located just steps from Resort Beach and the Virginia Beach Boardwalk, offering easy access to the sand, surf, and the city's lively atmosphere. It has consistently received excellent ratings from previous guests, highlighting its comfortable accommodations and convenient location. The apartment features a single bedroom and bathroom, providing ample space for up to three guests within its 300 square feet. Enjoy amenities like a fully equipped kitchen, air conditioning, a swimming pool, a balcony, free Wi-Fi, and a washing machine, making it easy to relax and enjoy your Virginia Beach vacation.
10 1 review
Chesapeake Bay
06/27 – 07/04
$207/nighttotal: $1449 (7 )
Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony
1 3
resort , Virginia Beach
Barclay Towers Resort, located in the Northeast Virginia Beach district directly on the Virginia Beach Boardwalk, offers oceanfront units with easy access to the beach and attractions like Pacific Avenue and the Veterans United Home Loans Amphitheater. The Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony features one-bedroom suites accommodating up to four guests, complete with a full kitchen, an indoor pool, hot tub, fitness center, and free garage parking across the street.
Find the Best Seaside Vacation Rentals in Chesapeake Bay
Relax near the shore in these coastal Chesapeake Bay vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.
9.6 9 reviews
Chesapeake Bay
07/30 – 08/05
$285/nighttotal: $1710 (6 )
Steps To Chesapeake Bay! 'Callaway Drive Retreat'
3 6
house , Shady Side
Chesapeake Bay
08/23 – 08/28
$204/nighttotal: $1020 (5 )
Beach Bliss In Hampton Minutes To The Shore!
2 2
apartment , Hampton
10 14 reviews
Chesapeake Bay
08/29 – 09/05
$278/nighttotal: $1946 (7 )
Unique Tangier Cottage W/ Chesapeake Bay Views!
4 2
cottage , Tangier
8.5 5196 reviews
Chesapeake Bay
08/23 – 08/28
$162/nighttotal: $810 (5 )
Delta Hotels By Marriott™ Virginia Beach Waterfront Suites
1 2
resort , Virginia Beach
Compare Luxury Vacation Rentals in Chesapeake Bay
Refined interiors and prime locations make these luxury waterfront vacation rentals in Chesapeake Bay the ideal choice for your stay.
9.4 27 reviews
Chesapeake Bay
10/01 – 10/05
$167/nighttotal: $668 (4 )
Pet-friendly 2br- Near Beach, Bases, & Hospitals
2 3
apartment , Norfolk
Discover Vacation Rentals with Saunas in Chesapeake Bay
Maximize your wellness with vacation rentals in Chesapeake Bay featuring on-site saunas and steam rooms.
