6706 Vacation rentals and Airbnb in Chesapeake Bay
10 1 review
Chesapeake Bay
30/07 – 03/08
₹71853/nighttotal: ₹287412 (4 )
4br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12
4 10
house , Arnold
This four-bedroom property in Annapolis is situated 12.7 kilometres from Annapolis Harbour and 37 kilometres from Baltimore's Inner Harbour. This spacious residence accommodates up to 12 guests, offering a fully equipped kitchen with a dishwasher, an on-site bar, a garden, and private parking, with a floor area of 17 square metres.
9.2 9 reviews
Chesapeake Bay
30/07 – 05/08
₹23057/nighttotal: ₹138342 (6 )
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.
1 6
cottage , Benedict
This Benedict beach house is situated near the Dr Samuel A Mudd House Museum and Drum Point Lighthouse, offering private beach access with over 150 metres of shoreline and a 120-metre pier, and is a 15-minute drive (approx. 24km) from local amenities. Sleeping six, this self-catering property boasts a queen bed, bunk beds, and a sofa bed, plus a fully equipped kitchen, air conditioning, a terrace, garden, spa, and a gas grill; enjoy birdwatching at Walter's Walk sandbar and explore nearby attractions.
Chesapeake Bay
30/07 – 03/08
₹95699/nighttotal: ₹382796 (4 )
All Tucked Inn
1 10
house , Annapolis
All Tucked Inn, a one-bedroom Annapolis property, is situated 4km from Annapolis Harbour and 47km from Baltimore attractions including the Inner Harbour and Camden Yards. This self-catering house sleeps 15 guests and boasts three bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, and on-site parking; enjoy nearby Baltimore-Washington International Airport (32km).
10 182 reviews
Chesapeake Bay
29/08 – 05/09
₹18887/nighttotal: ₹132209 (7 )
Summer Escape - Dock, Pool, Firepits, & Kayaks
1 2
house , Gloucester Courthouse
This Gloucester Courthouse guesthouse, situated on 10 acres near Bland Creek, is 24km from Gloucester's town centre, 48km from the Yorktown Riverwalk, and 72km from Williamsburg's historical attractions. The two-bedroom apartment, boasting a large screened porch and access to a shared saltwater pool (rental optional), sleeps four and includes a full kitchen, washer/dryer, high-speed internet, and smart TVs, alongside 10 acres of private woodland ideal for exploring.
9.6 86 reviews
Chesapeake Bay
02/07 – 05/07
₹8361/nighttotal: ₹25083 (3 )
Home Away
1 2
apartment , Fort Meade
This Hanover apartment, situated approximately 23-24 km from Baltimore attractions such as Carroll Park, the Sports Legends Museum at Camden Yards, and the Baltimore Convention Center, and 9 km from Baltimore/Washington International Thurgood Marshall Airport, offers convenient access to Fort Meade and wider Baltimore. The 70-square-metre one-bedroom flat provides comfortable accommodation for two guests, featuring a fully equipped kitchenette, free Wi-Fi, on-site parking, and a private entrance; nearby attractions include the Inner Harbor and Federal Hill.
9.9 311 reviews
Chesapeake Bay
05/07 – 08/07
₹22337/nighttotal: ₹67011 (3 )
The Cottage On Sarah's Creek
2 4
apartment , Gloucester Point
This charming cottage is located on Sarah's Creek, just 40km from historic Williamsburg and 16km from Yorktown Beach, offering a peaceful retreat with easy access to local attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. The cottage has one bedroom with a California King bed, a loft with a queen bed and a pool table, and a small living area with a futon, sleeping up to four guests. Enjoy the waterfront location with two kayaks for exploring the creek, a relaxing backyard with a fire pit and yard games, and a fully equipped kitchen with modern amenities like a washer/dryer and Roku TVs.
9.8 7 reviews
Chesapeake Bay
29/08 – 05/09
₹20771/nighttotal: ₹145397 (7 )
Walk To Beach: Pet-friendly Gem In Scotland!
1 2
cottage , Piney Point
This Piney Point holiday home is situated near Point Lookout State Park (1.6 km), Buzz's and Drury's Marinas (6.4 km), and Piney Point Lighthouse (43.5 km), offering easy access to Chesapeake Bay beaches. The 39 square metre self-catering property sleeps three, features a sunroom, fully equipped kitchen with a Keurig coffee machine, a furnished deck with charcoal grill, driveway parking for three vehicles, and allows one pet for a fee.
10 79 reviews
Chesapeake Bay
30/07 – 05/08
₹18805/nighttotal: ₹112830 (6 )
Idle Hour, A Tranquil 3 Bedroom 1.5 Bath Cottage With Dock & Golf Cart Rental
3 6
cottage , Smith Island
This charming waterfront cottage is situated just 200 metres from Terrapin Sand Point and 4 kilometres from Smith Island, offering easy access to both the island's attractions and the beautiful beaches of the point. It consistently receives excellent ratings for location, cleanliness, and overall user experience. The cottage features three bedrooms, comfortably accommodating up to six guests. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a terrace, and a barbecue grill, perfect for relaxing evenings and enjoying the stunning water views.
9.8 29 reviews
Chesapeake Bay
30/07 – 05/08
₹20549/nighttotal: ₹123294 (6 )
Bubba Butler's Cottage
3 6
cottage , Urbanna
This Locust Hill cottage, near Urbanna, Virginia, is conveniently located within 15km of the Middlesex County Museum, Piankatank River Golf Club, and Urbanna Historic District, and 19km from White Stone Beach. This three-bedroom, two-bathroom holiday home sleeps six, offering in-unit laundry facilities, a hair dryer, and iron, and is ideal for exploring the Northern Neck's historical sites and natural beauty.
9.7 6 reviews
Chesapeake Bay
27/06 – 04/07
₹18710/nighttotal: ₹130970 (7 )
Four Sails - Oceanfront And City View Balconies!
1 3
apartment , Virginia Beach
This oceanfront apartment is located at the northern end of Virginia Beach's boardwalk, near numerous restaurants and a 16km drive from Ocean Breeze Water Park, with Colonial Williamsburg, Yorktown, and Jamestown also within easy reach. This one-bedroom, one-bathroom condo offers a king-sized bed, a pull-out queen-sized sofa bed sleeping four, a fully equipped kitchen, and access to resort amenities including an indoor heated pool, fitness centre with sauna, and free bikes for exploring the 5km boardwalk; daily housekeeping is provided.
10 2 reviews
Chesapeake Bay
30/07 – 03/08
₹93661/nighttotal: ₹374644 (4 )
5 Mi To Inner Harbor: Expansive Family Getaway
6 10
house , Baltimore
This Baltimore property is situated approximately 6.4 kilometres from the Inner Harbour and within a 4.8-6.4 kilometre radius of the Edgar Allan Poe House, Baltimore Zoo, Walters Art Museum, Baltimore Museum of Art, University of Maryland, Baltimore, and Johns Hopkins University. This six-bedroom, six-bathroom house offers 418 square metres of space, accommodating up to 25 guests and boasting amenities including a fully equipped kitchen, spa, in-house laundry, fireplace, private yard, and free Wi-Fi.
9.9 157 reviews
Chesapeake Bay
05/07 – 08/07
₹15432/nighttotal: ₹46296 (3 )
Water View Cottage
2 4
apartment , Deal Island
This Deal Island holiday home is situated a short walk from a shared pier, offering easy access to rockfishing and a short drive from a boat ramp for watercraft. Sleeping up to five guests in two bedrooms and one bathroom, this self-catering property boasts a fully equipped kitchen, air conditioning, a garden, and excellent internet access, perfect for exploring the island's kayaking opportunities and birdwatching spots.
Best family friendly Chesapeake Bay vacation rentals
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals
8.6 39 reviews
Chesapeake Bay
30/07 – 05/08
₹49503/nighttotal: ₹297018 (6 )
Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed
3 6
cottage , Norfolk
This charming beach house is situated in Willoughby Spit, just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. The cottage is rated very good by previous guests. This comfortable holiday home has three bedrooms and can accommodate up to eight guests. The property includes a fully equipped kitchen, a fireplace, a patio, a garden, and free Wi-Fi, as well as a playground and barbecue grills for guests to enjoy.
9.6 4 reviews
Chesapeake Bay
02/07 – 05/07
₹17520/nighttotal: ₹52560 (3 )
Charming Lower Level Guest Unit, Fully Equipped Kitchen, Wifi, Free Onsite Park
1 2
apartment , Glen Burnie
This Pasadena apartment, minutes from Downs Park and the Baltimore & Annapolis Trail, offers easy access to attractions such as the Baltimore Cruise Terminal and Arundel Mills Mall. The 111-square-metre (1194 sq ft) self-catering flat features one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, free parking, and a spa.
Chesapeake Bay
30/07 – 03/08
₹88355/nighttotal: ₹353420 (4 )
Coles Point Marina And Campground
2 10
house , Montross
This detached house is situated in Hague, 48 kilometres from Memorial House and the George Washington Birthplace National Monument, and 112 kilometres from Richmond International Airport. This property offers a private entrance, air conditioning, complimentary WiFi, free private parking, and a well-equipped kitchen with a fridge, microwave, and dishwasher, providing a comfortable stay for guests visiting Montross.
10 373 reviews
Chesapeake Bay
29/08 – 05/09
₹21894/nighttotal: ₹153258 (7 )
Cottage On A Private Island In The York River
3 2
cottage , Gloucester Point
This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay. This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.
Best Chesapeake Bay vacation rentals with a pool
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool
8.6 1686 reviews
Chesapeake Bay
02/07 – 05/07
₹27225/nighttotal: ₹81675 (3 )
Rod 'N' Reel Resort
1 2
resort , Chesapeake Beach
Rod 'N' Reel Resort is situated on the Chesapeake Bay, a short drive from North Beach and Twin Shields Golf Club, making it a convenient base for exploring the area. The resort enjoys excellent ratings for its location, cleanliness, and overall experience. The resort offers a range of accommodation options, including rooms with balconies and water views. Guests can enjoy a variety of amenities, including a swimming pool, fitness centre, spa, and on-site dining options, as well as activities like fishing charters and casino entertainment.
9.8 77 reviews
Chesapeake Bay
30/07 – 03/08
₹103166/nighttotal: ₹412664 (4 )
Bury Oasis: Pool, Hottub, Movie Theatre, Game Room
4 10
apartment , Salisbury
This four-bedroom apartment is situated in a residential area near Salisbury University, approximately 5 kilometres from local restaurants and 40 kilometres from the beach in Ocean City. The property boasts a large backyard with a swimming pool, hot tub, and a spacious deck, ideal for families and groups of up to 12 guests.
8.0 2 reviews
Chesapeake Bay
02/07 – 05/07
₹69239/nighttotal: ₹207717 (3 )
Lovely 1 Bedroom By The Beach, W/ Porch & Pool
1 2
apartment , Virginia Beach
This Virginia Beach holiday home is situated in Northeast Virginia Beach, a short walk (0.8km) from Pacific Avenue and the Virginia Beach Boardwalk, and 4km from Sandbridge Beach, offering easy access to local attractions. This self-catering property boasts 70 square metres of space, comprising one bedroom, one bathroom, and sleeping up to four guests; features include a swimming pool, tennis court, and free Wi-Fi.
Chesapeake Bay
29/08 – 05/09
₹44039/nighttotal: ₹308273 (7 )
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
2 2
house , Virginia Beach
This oceanfront apartment offers direct access to Virginia Beach, situated a mere 200 metres from the Virginia Beach Boardwalk. This two-bedroom, two-bathroom apartment sleeps up to six guests and features a fully equipped kitchen, a balcony with sea views, air conditioning, and access to a communal fitness centre, with WiFi provided and a check-out time of 10:00 AM.
Frequently asked questions about holiday rentals in Chesapeake Bay
What are the top family-friendly attractions in Baie de Chesapeake?
The Maryland Science Center in Baltimore is a fantastic place for kids of all ages, and the National Aquarium is another great option. For a more outdoorsy experience, Assateague Island National Seashore is a beautiful beach with wild horses.
What are the best Airbnb and vacation rentals in Chesapeake Bay?
When is the best time to book a vacation rental in Baie de Chesapeake?
You'll want to book your vacation rental well in advance, especially if you're travelling during peak season, which is typically from June to August. This will give you the best choice of properties and ensure you get the dates you want.
What are the most popular Airbnbs in Chesapeake Bay?
What events or festivals should visitors check out in and around Baie de Chesapeake?
The Chesapeake Bay Wine Festival in Stevensville is a great event for wine lovers, and the National Folk Festival in Salisbury is a fantastic celebration of music and culture. You can also check out the annual Oyster Festival in St. Michaels.
What are the best vacation rentals with a pool in Chesapeake Bay?
What are the best budget-friendly activities in Baie de Chesapeake?
Take a walk along the Chesapeake Bay Trail, it's a scenic path that stretches for miles, and it's completely free. You can also visit one of the many state parks in the area, such as Assateague Island National Seashore, for a day of hiking, swimming, or just relaxing.
What are the best rentals for families and kids in Chesapeake Bay?
What are the best restaurants with local dishes in Baie de Chesapeake?
For a taste of the Chesapeake Bay, try the crab cakes at The Chart House in Annapolis. If you're looking for something a bit more casual, The Crab Claw in Cambridge is a great option for fresh seafood.
What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?
What are the best walking or cycling routes in Baie de Chesapeake?
The Chesapeake Bay Trail is a great option for both walking and cycling, it offers stunning views of the Bay. For a shorter ride, check out the scenic loop around the town of St. Michaels.
Are there pet-friendly attractions in Baie de Chesapeake?
Many of the beaches in the area are dog-friendly, including Assateague Island National Seashore. You can also find plenty of pet-friendly restaurants and cafes.
What are the benefits of choosing a vacation rental in Baie de Chesapeake?
Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities, which can be very convenient for families. They also tend to be more affordable than hotels, especially if you're travelling with a large group.
What are the top sports attractions and facilities in Baie de Chesapeake?
The M&T Bank Stadium in Baltimore is home to the Baltimore Ravens, and the Camden Yards is home to the Baltimore Orioles. If you're interested in sailing, the Annapolis Yacht Club is a great place to watch races.
Destinations nearby
Best Chesapeake Bay holiday rentals with a balcony
8.4 11 reviews
Chesapeake Bay
29/08 – 05/09
₹26759/nighttotal: ₹187313 (7 )
Sun Outdoors Cape Charles
2 2
house , Cape Charles
This beachfront property is located in Cape Charles, Virginia, just 60 kilometres from Norfolk International Airport and a short distance from the town centre. The house has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests, across a floor area of 399 square metres. Enjoy a range of amenities, including a saltwater pool, a private beach area, a fully equipped kitchenette, and a terrace.
10 1 review
Chesapeake Bay
30/07 – 05/08
₹37943/nighttotal: ₹227658 (6 )
13 Mi To Annapolis: Dog-friendly Home W/ Fire Pit!
3 6
house , Crofton
This dog-friendly Crofton house, situated approximately 21 kilometres from Annapolis and 35 kilometres from Washington, D.C., offers easy access to Annapolis Harbour and Baltimore-Washington International Airport. The 174 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi.
9.8 9 reviews
Chesapeake Bay
30/07 – 03/08
₹38122/nighttotal: ₹152488 (4 )
Cottage On The Bay
3 10
apartment , Fishing Creek
This charming cottage is located on Hoopers Island in Fishing Creek, a peaceful rural area on the Chesapeake Bay, within half a mile of a free county boat ramp. The property has received excellent ratings from previous guests. This three-bedroom, two-bathroom holiday home offers ample space for families or groups. The cottage is fully equipped with a kitchen, fireplace, washer/dryer, and a terrace, and guests can enjoy access to fishing and crabbing charters, kayaks, and boat docking facilities at the nearby Riverside Lodge.
8.0 1 review
Chesapeake Bay
29/08 – 05/09
₹26507/nighttotal: ₹185549 (7 )
Beach Days & Dtwn Charm! Cape Charles Cottage
2 2
house , Cheriton
This holiday cottage in Cheriton is situated approximately 51 kilometres from Norfolk International Airport, offering a coastal escape. This 98 square metre holiday home accommodates up to 13 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, complimentary on-site parking, and free WiFi, along with a private patio and outdoor dining area.
Best Chesapeake Bay holiday rentals with parking
10 1 review
Chesapeake Bay
02/07 – 05/07
₹21648/nighttotal: ₹64944 (3 )
Baltimore Home < 2 Mi To Dtwn Towson
1 2
house , Baltimore
This charming Baltimore house is situated in Towson, less than 3.2 km from downtown Towson, 6.4 km from the Baltimore Museum of Art, and 6.6 km from Clifton Park, offering a peaceful suburban setting close to the city's attractions. The property provides a comfortable and convenient stay, with a fully equipped kitchen, a washing machine, and free Wi-Fi. The house has one bedroom and one bathroom, with a floor area of 60 square metres, comfortably accommodating two guests. Amenities include a flat-screen TV, towels, bed linen, and parking, ensuring a pleasant and relaxing stay.
9.8 187 reviews
Chesapeake Bay
29/08 – 05/09
₹12117/nighttotal: ₹84819 (7 )
Cabin At Holdens Creek On Eastern Shore Of Va
1 2
cabin , Sanford
This cabin is located in a peaceful rural setting, just 25 kilometres from Bloxom Winery, Wallops Flight Facility, and the Eastern Shore Railway Museum. It has received excellent user ratings. The cabin is a one-bedroom, one-bathroom property with a floor area of 74 square metres and a capacity of six guests. It offers a range of amenities including a kitchen with a fridge and microwave oven, air conditioning, a terrace, a garden, parking, and free Wi-Fi.
Chesapeake Bay
02/07 – 05/07
₹14461/nighttotal: ₹43383 (3 )
Hearing Accessible King Studio W/ Free Breakfast
1 2
studio , Baltimore
This communications-accessible apartment is located in Baltimore's Inner Harbour, 500 metres from Historic Ships in Baltimore and 600 metres from the National Aquarium. This studio apartment accommodates two guests and offers a fully equipped kitchen with a full-size fridge, dishwasher, and stovetop, as well as complimentary hot breakfast, evening receptions, and free WiFi.
9.5 187 reviews
Chesapeake Bay
29/08 – 05/09
₹22978/nighttotal: ₹160846 (7 )
Restored 1920's Cottage On 1 Acre W/ Fire Pit
2 2
house , Gloucester Point
This charming cottage is located in Hayes, Virginia, just a short drive from popular attractions like Busch Gardens, Colonial Williamsburg, and Historic Jamestowne. The property has received excellent ratings for its cleanliness, location, and overall experience. The 84 square metre cottage comfortably sleeps up to 6 guests and features a fully equipped kitchen, a garden, a spa, and a fire pit for relaxing evenings. Enjoy the scenic river views, the spacious acreage, and the restored 1920s character of this unique property.