This detached property in Elkton is situated 22 kilometres from New Castle Airport. This dwelling accommodates up to eleven guests and features two bathrooms, a fully equipped kitchen, complimentary Wi-Fi, and private parking, with a non-smoking policy in effect.
9.0 33 reviews
Chesapeake Bay
23/08 – 28/08
136 €/nighttotal: 680 € (5 )
Cozy Modern Micro Apt In The Heart Of Fells Point!
2 2
apartment , Baltimore
This Baltimore waterfront apartment, less than 1.6km from the Inner Harbour and attractions such as the National Aquarium and Johns Hopkins Hospital, offers easy access to public transport and scenic views. This 60 square metre, two-bedroom flat sleeps four guests and boasts a fully equipped kitchen, swimming pool, spa, parking, and free Wi-Fi; on-site amenities include a water park and barbecue grills.
Chesapeake Bay
27/06 – 04/07
138 €/nighttotal: 966 € (7 )
Cozy Baltimore Studio Apts
1 3
studio , Baltimore
This Parkville flat offers proximity to Clifton Park, located 6.28 kilometres away, and is within a 11.27 kilometre radius of Towson University, Johns Hopkins University, and the Baltimore Museum of Art. This studio apartment accommodates up to five guests and features a kitchenette with a microwave, complimentary WiFi, and private parking, with cycling opportunities available in the surrounding area.
9.7 3 reviews
Chesapeake Bay
30/07 – 05/08
218 €/nighttotal: 1308 € (6 )
Midlong Term Rental Cozy Home At Mary Roberts
2 6
house , Newport News
This detached house in Stoney Brook Estates, Newport News, offers a peaceful residential setting with convenient access to attractions, being 16 kilometres from Busch Gardens and Water Country, 13.5 kilometres from the Virginia Living Museum, and 24 kilometres from Colonial Williamsburg. This property spans 102 square metres and accommodates up to 10 guests with air conditioning, free Wi-Fi, a fully equipped kitchen including a dishwasher and microwave, two bathrooms, and private parking, alongside a private patio for outdoor relaxation.
8.5 5196 reviews
Chesapeake Bay
23/08 – 28/08
140 €/nighttotal: 700 € (5 )
Delta Hotels By Marriott™ Virginia Beach Waterfront Suites
1 2
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.
9.5 2 reviews
Chesapeake Bay
27/06 – 04/07
162 €/nighttotal: 1134 € (7 )
Downtown And Inner Harbor Apartment
1 3
apartment , Baltimore
This one-bedroom flat offers a prime downtown Baltimore location, just a 6-minute walk to the Sports Legends Museum at Camden Yards and 0.8 kilometres from the University of Maryland – Baltimore, with Carroll Park, Power Plant, the Walters Art Museum, and Pier Six Concert Pavilion also within 1.9 kilometres. This 53 square metre serviced apartment, which can accommodate up to five guests, features complimentary private parking, free Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and a private entrance for your convenience.
9.5 112 reviews
Chesapeake Bay
01/10 – 05/10
161 €/nighttotal: 644 € (4 )
Virginia Beach Studio With Balcony And Pool View!
1 3
studio , Virginia Beach
This studio apartment is situated in Virginia Beach, just a short walk from the beach and 1.5km from Neptune's Park, with Virginia Beach Fishing Pier 3km away and The Virginia Beach Convention Center 3.5km away. The apartment has received excellent ratings for location, cleanliness, and user experience, making it an ideal choice for travellers seeking a comfortable and convenient stay. The studio is perfect for a small family or group of friends, offering 30 square metres of space and accommodating up to 3 guests. The apartment features a fully equipped kitchen, a private balcony with sea views, access to a swimming pool, and a peaceful garden, providing everything needed for a relaxing and enjoyable holiday.
9.9 268 reviews
Chesapeake Bay
01/10 – 05/10
117 €/nighttotal: 468 € (4 )
Cozy Little Cottage
1 3
apartment , California
This two-bedroom cottage near Solomons Island, Maryland offers easy access to the boardwalk and is within a short distance (distances unspecified) of historical attractions, lighthouses, and opportunities for fishing, crabbing, and shark tooth hunting. The property features an open-plan layout suitable for families, sleeps four guests, and includes a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and excellent user ratings for cleanliness and location.
9.9 66 reviews
Chesapeake Bay
27/06 – 04/07
141 €/nighttotal: 987 € (7 )
El Camino
1 3
house , Piney Point
This Piney Point guesthouse, situated near Jutland Creek and a 7-minute (approximately 4.5 km) drive from St. Mary's College of Maryland, offers secluded waterfront accommodation. The self-contained unit features one bedroom plus a sofa bed sleeping three, a private dock on Jutland Creek with stunning Potomac River views, an outdoor grill, and shared access to a beautiful dock ideal for wildlife viewing.
8.8 219 reviews
Chesapeake Bay
27/06 – 04/07
184 €/nighttotal: 1288 € (7 )
Heaven On Baltimore Downtown Fully Furnished Apartments
2 3
apartment , Baltimore
This apartment is ideally located in downtown Baltimore, just a short walk from the Sports Legends Museum at Camden Yards and the Baltimore Convention Center, making it perfect for exploring the city's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment is well-equipped with a fully equipped kitchen, a comfortable living space, and a terrace for enjoying the fresh air. Guests can enjoy a range of amenities, including a fitness centre, swimming pool, and parking, as well as access to a restaurant and bar on-site.
9.8 315 reviews
Chesapeake Bay
23/08 – 28/08
148 €/nighttotal: 740 € (5 )
The Heron's Nest At Atlantic Marina
1 2
cottage , Lake Shore
This charming lakeside retreat is located in Pasadena, Maryland, just a short drive from historical landmarks and art galleries. It has received excellent reviews from previous guests. The cottage offers 54 square metres of living space, accommodating up to four guests in a comfortable layout with one bedroom and one bathroom. You can enjoy a range of amenities including a swimming pool, a terrace, and a garden, and the property is perfect for enjoying water activities like fishing and boating.
9.8 33 reviews
Chesapeake Bay
01/10 – 05/10
149 €/nighttotal: 596 € (4 )
Bee Humble Cottage W/in 20mins To Public Beaches
2 3
cottage , Gloucester Courthouse
This family-friendly cottage is located in a peaceful rural area of Gloucester Courthouse, just 13km from Riverside Walter Reed Hospital and within a 32km radius of Gloucester Point Beach Park and Machicomoco State Park. It has received excellent user ratings, making it a popular choice for travellers seeking a relaxing escape. The two-bedroom cottage spans 102 square metres and comfortably accommodates up to four guests. It offers a range of amenities, including a fully equipped kitchen, a private garden, a swimming pool, a spa, and access to a nearby water park, ensuring a comfortable and enjoyable stay.
Best family friendly Chesapeake Bay holiday rentals
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals
9.9 130 reviews
Chesapeake Bay
30/07 – 05/08
436 €/nighttotal: 2616 € (6 )
The Little Blue Cottage - Topping : Waterfront!
3 6
cottage , White Stone
This waterfront cottage is situated in White Stone, Virginia, just a short drive from award-winning restaurants and a marina. The cottage has consistently received excellent reviews for its location, cleanliness, and overall experience. The cottage spans 126 square metres and comfortably accommodates up to six guests in its three bedrooms and two bathrooms. Enjoy stunning views of the bay and creek from the porch swings, take advantage of the high-speed internet, and explore the area by kayak, launching from the floating dock or nearby community boat ramp.
10 225 reviews
Chesapeake Bay
30/07 – 05/08
409 €/nighttotal: 2454 € (6 )
Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna
3 6
cottage , Mayo
This family-friendly cottage is situated in Edgewater, Mayo, just a short drive from Triton Beach and other local attractions. It enjoys an excellent user rating, making it a popular choice for families seeking a relaxing getaway. The three-bedroom property, spanning 172 square metres, comfortably accommodates up to 11 guests. Enjoy a fully equipped kitchen, a spacious garden, and a terrace, perfect for al fresco dining and taking in the scenic views.
9.6 49 reviews
Chesapeake Bay
29/08 – 05/09
160 €/nighttotal: 1120 € (7 )
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.
1 2
cottage , Shady Side
This waterfront cottage in Shady Side, Maryland, is situated on a peninsula on the West River, approximately 32 kilometres from Annapolis and close to Galesville. The one-bedroom, one-bathroom property sleeps three, offering a private dock, kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, internet access, and proximity to Thanksgiving Farm Wines and South River Golf Links.
9.6 58 reviews
Chesapeake Bay
27/06 – 04/07
545 €/nighttotal: 3815 € (7 )
Coastal Charmer - Chesapeake Properties
4 3
apartment , Cape Charles
This charming four-bedroom apartment is located in Cape Charles, a short walk from the beach and Mason Avenue's shops. The property has received excellent ratings for location, cleanliness, and overall experience. The 149 square metre apartment comfortably sleeps up to 10 guests and features a modern kitchen, a washer and dryer, and high-speed internet. Guests can enjoy the wraparound porch with seating, the backyard with a grill, corn hole/sombo games, and an outdoor shower.
Best Chesapeake Bay holiday rentals with a pool
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool
9.8 450 reviews
Chesapeake Bay
30/07 – 05/08
383 €/nighttotal: 2298 € (6 )
Kingsmill Condo On Golf Course 9th Fairway! Local Owner
2 6
apartment , Williamsburg
This Williamsburg apartment is located just 1.6 kilometers from Busch Gardens Williamsburg, a short drive from the popular theme park, and within walking distance of the Kingsmill Plantation Golf Course and Kingsmill Beach. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The apartment is 130 square meters in size and is suitable for families, offering a comfortable and spacious living space. The apartment is equipped with a range of amenities, including a swimming pool, tennis court, and garden, providing plenty of opportunities for relaxation and recreation.
Chesapeake Bay
30/07 – 05/08
932 €/nighttotal: 5592 € (6 )
Bohemia Manor Farm
3 6
house , Cecilton
This country house in Cecilton is located at Bohemia Manor Farm, Chesapeake City, 40 kilometres from the Old Dutch House and 27 kilometres from Dayett Station, with New Castle Airport 39 kilometres away. Guests can enjoy a private garden, complimentary WiFi, free parking, a fully equipped kitchen, an on-site restaurant, and a seasonal outdoor swimming pool, with air-conditioned rooms available.
9.7 105 reviews
Chesapeake Bay
30/07 – 05/08
336 €/nighttotal: 2016 € (6 )
Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md
2 6
apartment , Rock Hall
This charming cottage is situated on Bayside Avenue in Rock Hall, Maryland, just a short stroll from the town beach and swimming pool. It has consistently received excellent ratings for location, cleanliness, and overall guest experience. The two-bedroom cottage, spanning 93 square metres, comfortably accommodates up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a screened back deck, and a pet-friendly policy.
9.8 130 reviews
Chesapeake Bay
27/06 – 04/07
272 €/nighttotal: 1904 € (7 )
Patuxent River View
2 3
house , Dunkirk
This Dunkirk guest house is situated near North Beach, Maryland, approximately 65km from Washington D.C., offering easy access to Annapolis, Baltimore, and Solomons Island. This 84 square metre self-catering property features two bedrooms, one bathroom, a fully equipped kitchen, and a swimming pool, sleeping up to four guests and providing a comfortable stay with free Wi-Fi and spectacular views.
Frequently asked questions about holiday rentals in Chesapeake Bay
When is the best time to book a vacation rental in Baie de Chesapeake?
It really depends on what you want to do. If you're looking for warm weather and beaches, July and August are popular months. For a quieter experience, consider visiting in the spring or autumn. Booking in advance is always a good idea, especially during peak season.
What are the best Airbnb and holiday rentals in Chesapeake Bay?
What are the best walking or cycling routes in Baie de Chesapeake?
The Chesapeake Bay Trail is a great option, with over 300 km of paved and unpaved trails. For a shorter walk, the Annapolis City Dock is a lovely spot to stroll along the waterfront. For a more challenging bike ride, try the Eastern Shore Bike Trail, which runs along the Chesapeake Bay.
What are the most popular Airbnbs in Chesapeake Bay?
Are there pet-friendly attractions in Baie de Chesapeake?
Many of the beaches and parks in the area are dog-friendly, including Assateague Island National Seashore and Sandy Point State Park. The Chesapeake Bay Maritime Museum in St. Michaels also welcomes dogs on leashes.
What are the best holiday rentals with a pool in Chesapeake Bay?
Best Chesapeake Bay holiday rentals with a balcony
9.0 8 reviews
Chesapeake Bay
30/07 – 05/08
209 €/nighttotal: 1254 € (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.
9.1 726 reviews
Chesapeake Bay
29/08 – 05/09
600 €/nighttotal: 4200 € (7 )
Kings Creek Plantation By Tripforth
3 2
house , Williamsburg
King's Creek Resort By Endless Resorts is conveniently located just outside Williamsburg's historic district, offering easy access to both theme parks and the historic landmarks of Colonial Williamsburg, which is just 7.2 miles away. The resort has received excellent ratings for its location, cleanliness and overall user experience. The resort offers a range of accommodation options, including rooms and suites. Guests can enjoy amenities such as a swimming pool, fitness centre, restaurant and spa, as well as activities like mini-golf and a playground for families.
9.8 187 reviews
Chesapeake Bay
29/08 – 05/09
110 €/nighttotal: 770 € (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.
9.3 58 reviews
Chesapeake Bay
23/08 – 28/08
129 €/nighttotal: 645 € (5 )
Gaia House
2 2
house , Annapolis
Gaia House, in Annapolis, is situated 6 kilometres from Annapolis Harbour and within a 32-48 kilometre radius of Baltimore attractions including the Inner Harbour and Historic Ships in Baltimore. This two-bedroom property, offering 9 square metres of floor space, sleeps seven guests and features a fully equipped kitchen, private parking, Wi-Fi, air conditioning, and a patio with quiet street views.
Best Chesapeake Bay holiday rentals with parking
8.9 6534 reviews
Chesapeake Bay
01/10 – 05/10
117 €/nighttotal: 468 € (4 )
Club Wyndham Kingsgate
1 3
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.
9.8 481 reviews
Chesapeake Bay
23/08 – 28/08
120 €/nighttotal: 600 € (5 )
Cozy Fells Point Gem / In The Heart Of Fells Point
1 2
apartment , Baltimore
This one-bedroom flat is located in Fells Point, a historic waterfront district in Baltimore, within a mile of Fell's Point Visitor Center and Johns Hopkins Hospital. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers. The flat is 56 square metres and features a fully equipped kitchen with a fridge, oven, microwave, and dishwasher. You can enjoy the on-site spa, relax in the smoke-free environment, and stay connected with free Wi-Fi and a Smart TV.
9.6 74 reviews
Chesapeake Bay
29/08 – 05/09
307 €/nighttotal: 2149 € (7 )
Updated North Beach Cottage Pet Friendly!
3 2
house , North Beach
This North Beach cottage is located in Deale, Maryland, just 43 kilometres from Annapolis Harbour and 43 kilometres from Addison Road-Seat Pleasant. The property has received excellent ratings for its cleanliness, location, and overall user experience. The cottage offers 3 bedrooms and 2 bathrooms across 134 square metres, comfortably accommodating up to 8 guests. The property is pet-friendly, air-conditioned, and includes a swimming pool, spa, garden, parking, a fully equipped kitchen, washing machine, Wi-Fi, cable TV, and a patio.
9.4 14 reviews
Chesapeake Bay
29/08 – 05/09
154 €/nighttotal: 1078 € (7 )
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment
1 2
house , Brock Hall
This Brock Hall house, near Addison Road-Seat Pleasant Station (22km) and approximately 32km from both the Supreme Court and the US Capitol, offers a convenient base for exploring the area. The 223-square-metre property boasts a private pool, garden, terrace, fitness centre, and parking, accommodating up to six guests in its one-bedroom, one-bathroom layout with a fully equipped kitchenette.