Spacious North East Home With Fenced Yard And Fire Pit
5 10
house , North East
This five-bedroom house in North East, Maryland, is situated 26 kilometres from tennis courts and 27 kilometres from the University of Delaware, offering easy access to local attractions within a 40-kilometre radius. The 185-square-metre property boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, air conditioning, a garden, parking, and accommodates up to 19 guests, perfect for large family gatherings or group getaways.
9.9 157 reviews
Chesapeake Bay
05/07 – 08/07
140 €/nighttotal: 420 € (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.
9.7 3 reviews
Chesapeake Bay
30/07 – 05/08
226 €/nighttotal: 1356 € (6 )
Cozy Condo Near Portsmouth Naval
3 6
house , Portsmouth
This Portsmouth apartment is located 15.1 kilometres from Norfolk Botanical Garden and 33.8 kilometres from the King Neptune Statue, offering convenient access to Portsmouth Naval. This property boasts a floor area of 102 square meters, accommodates up to 10 guests, and includes a well-equipped kitchen with a dishwasher, air conditioning, free WiFi, and private parking, with a private patio for relaxation.
8.0 7626 reviews
Chesapeake Bay
27/06 – 04/07
178 €/nighttotal: 1246 € (7 )
The Barclay Towers Hotel And Resort
1 3
resort , Virginia Beach
The Barclay Towers Hotel and Resort is situated in Virginia Beach, offering oceanfront accommodation a short walk from Adventure Parasail and a short drive from the Hampton Roads Naval Museum and Ocean Breeze Water Park. Each suite at this Virginia Beach hotel boasts a fully equipped kitchen, private balcony with an ocean view, sofa bed, cable TV, and access to an indoor pool, fitness centre, and free Wi-Fi.
Chesapeake Bay
30/07 – 03/08
636 €/nighttotal: 2544 € (4 )
Atlantic Haven
4 10
house , Virginia Beach
This Virginia Beach house, Atlantic Haven, is conveniently located near the boardwalk, 4.5km from the Cape Henry Lighthouse, and within 4.5km of Neptune's Park. Sleeping up to 19 guests, this four-bedroom, three-bathroom property boasts a fully equipped kitchen, free Wi-Fi, on-site parking, and is within easy reach of the Virginia Beach Fishing Pier and Convention Centre.
8.6 1686 reviews
Chesapeake Bay
05/07 – 08/07
153 €/nighttotal: 459 € (3 )
Rod 'N' Reel Resort
1 4
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.
9.6 4 reviews
Chesapeake Bay
27/06 – 04/07
125 €/nighttotal: 875 € (7 )
Charles Village 1-br, Walk To Johns Hopkins
1 3
apartment , Baltimore
This Charles Village apartment in Baltimore is situated a 15-minute walk from both MedStar Union Memorial Hospital and Johns Hopkins University, and within 4.8km of the National Aquarium and Baltimore Convention Centre. The one-bedroom flat sleeps three, offering a full kitchen with oven, stovetop, microwave and fridge, plus a washer, sofa bed, Smart TV, and games; nearby public transport includes North Avenue and Baltimore Penn Stations within a 30-minute walk.
9.9 311 reviews
Chesapeake Bay
05/07 – 08/07
202 €/nighttotal: 606 € (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.
10 5 reviews
Chesapeake Bay
29/08 – 05/09
168 €/nighttotal: 1176 € (7 )
Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac
2 2
cottage , Piney Point
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views. Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.
Chesapeake Bay
02/07 – 05/07
149 €/nighttotal: 447 € (3 )
2 Queen Studio W/ City View | Free Breakfast + Gym
1 2
studio , Baltimore
This studio apartment is situated in Baltimore's Inner Harbour, a 600-metre walk from the National Aquarium and 500 metres from Historic Ships in Baltimore. This two-queen-bed suite accommodates up to four guests and features a kitchen with a fridge, microwave, and dishwasher, alongside complimentary breakfast and an on-site fitness centre.
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.
10 3 reviews
Chesapeake Bay
30/07 – 05/08
334 €/nighttotal: 2004 € (6 )
Virginia Retreat With Porch And Grill, Near Beaches!
3 6
house , Wachapreague
This Wachapreague holiday home is situated approximately 43 kilometres from the Mid-Atlantic Regional Spaceport and 105 kilometres from Salisbury-Ocean City Wicomico Regional Airport. This three-bedroom property, boasting 130 square metres of floor space, comfortably sleeps 15 guests and includes a fully equipped kitchen with dishwasher and microwave, air conditioning, free Wi-Fi, and a washing machine.
Best family friendly Chesapeake Bay holiday rentals
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals
9.9 68 reviews
Chesapeake Bay
29/08 – 05/09
623 €/nighttotal: 4361 € (7 )
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger
3 2
cottage , Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings. The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
10 127 reviews
Chesapeake Bay
02/07 – 05/07
901 €/nighttotal: 2703 € (3 )
Charming Annapolis Victorian
6 2
apartment , Annapolis
This six-bedroom house is located in a peaceful neighbourhood, just a short walk from downtown Annapolis, the US Naval Academy, and the USNA Stadium. It has received excellent ratings for location, cleanliness, and overall experience. The house offers three floors of living space, comfortably accommodating up to 12 guests. It features a fully equipped kitchen, a jacuzzi, a terrace, a garden, and ample parking, making it ideal for families or groups seeking a comfortable and convenient stay.
9.0 151 reviews
Chesapeake Bay
02/07 – 05/07
251 €/nighttotal: 753 € (3 )
Waterfront Baltimore 2br Furnished Apartment Apts
2 2
apartment , Baltimore
This apartment is situated in Baltimore's waterfront district, just a short distance from Harbor East Marina, Pier Six Concert Pavilion, and Fell's Point, offering a lively and convenient location. It has been consistently rated very good for cleanliness, user experience, and location. The apartment is well-equipped with a modern kitchen, a terrace, and access to a swimming pool, a jacuzzi, a fitness centre, and free parking. Guests can enjoy the convenience of a concierge service, a restaurant, and free Wi-Fi, making for a comfortable and enjoyable stay.
Chesapeake Bay
27/06 – 04/07
204 €/nighttotal: 1428 € (7 )
102 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests
2 3
apartment , Baltimore
This downtown Baltimore flat is situated near Camden Yards, within walking distance of the Inner Harbour, Little Italy, and M&T Bank Stadium. The 94-square-metre (102 square meters converted to square feet and then to square meters) apartment features two bedrooms, two bathrooms, and accommodates up to five guests, offering a spacious open-plan layout, a terrace, in-unit laundry, and access to a fitness centre and parking.
Best Chesapeake Bay holiday rentals with a pool
Among the 6706 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool
10 5 reviews
Chesapeake Bay
27/06 – 04/07
757 €/nighttotal: 5299 € (7 )
Kingsbay Dockside Waterfront House
4 3
apartment , Fairmount
This Fairmount property, Kingsbay Dockside at 5757 Dockside Lane, offers breathtaking panoramic water views of Kingsbay Mansion across the water, the precise distance unspecified. This four-bedroom, eight-guest house boasts 278 square metres of space, including a newly renovated Swiss country-style interior with a modern kitchen, solarium, private swimming pool, and ample parking.
8.3 2880 reviews
Chesapeake Bay
30/07 – 05/08
480 €/nighttotal: 2880 € (6 )
The Atrium Resort, Virginia Beach By Vacatia
2 6
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.
8.2 3026 reviews
Chesapeake Bay
05/07 – 08/07
339 €/nighttotal: 1017 € (3 )
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia
1 4
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.
9.6 41 reviews
Chesapeake Bay
02/07 – 05/07
310 €/nighttotal: 930 € (3 )
2br Former Bank Vault Tower · Inner Harbor Views
2 2
apartment , Baltimore
This Downtown Baltimore flat is ideally located less than 1.6km from the CFG Bank Arena, Baltimore Convention Center, and National Aquarium, offering easy access to public transport and the Inner Harbour. The 111 square metre apartment sleeps six, boasting two bedrooms, one bathroom, a fully equipped kitchen, and on-site amenities including a swimming pool, fitness centre, and garden.
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
8.6 7 reviews
Chesapeake Bay
05/07 – 08/07
138 €/nighttotal: 414 € (3 )
Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer
2 4
apartment , Baltimore
This Berea property is conveniently located 2.4km from Johns Hopkins Hospital and 1.8km from the Maryland Institute College of Art, offering easy access to both medical facilities and cultural attractions. This two-bedroom, two-bathroom house sleeps four guests and features a fully equipped kitchen, free Wi-Fi, on-site parking, and a family-friendly playground nearby, making it ideal for families visiting Baltimore.
10 1 review
Chesapeake Bay
30/07 – 03/08
691 €/nighttotal: 2764 € (4 )
Water-view Deale Home Walk To Marina, Restaurants
5 10
house , Deale
This five-bedroom house in Deale, Maryland is situated just a short walk from the Deale Marina and local restaurants, offering easy access to the waterfront and local amenities, and is only 34 kilometres from Annapolis Harbour. The 232 square metre property features a fully equipped kitchen, a fireplace, a garden, and parking, and can accommodate up to 25 guests, making it ideal for large families or groups of friends.
Chesapeake Bay
05/07 – 08/07
197 €/nighttotal: 591 € (3 )
Suburban Comfort In Bowie! Apartment With Patio
1 4
apartment , Fairwood
This Bowie flat is located 16-24 kilometres from Addison Road-Seat Pleasant, the Supreme Court, Washington Union Station, and the U.S. Capitol, offering a suburban base for exploring the capital. This 65 square metre apartment can host up to 7 guests and features air conditioning, a fully equipped kitchen with a dishwasher and fridge, complimentary Wi-Fi, and a private patio with an outdoor dining area.
10 2 reviews
Chesapeake Bay
05/07 – 08/07
232 €/nighttotal: 696 € (3 )
Unique Tangier Cottage With Chesapeake Bay Views!
4 4
house , Tangier
This Tangier holiday home, sleeping up to 15 guests, is situated in an unspecified location within the city; its proximity to specific landmarks remains undisclosed. The 167 square metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen with dishwasher and microwave, air conditioning, free Wi-Fi, parking, and a terrace, perfect for families or large groups.
Best Chesapeake Bay holiday rentals with parking
Chesapeake Bay
30/07 – 05/08
244 €/nighttotal: 1464 € (6 )
Fish On-site Rappahannock River Gem!
3 6
house , Urbanna
This Urbanna holiday home is situated approximately 48 kilometres from Tradition at Stonehouse Golf Club and 69 kilometres from Newport News/Williamsburg International Airport. The 204 square metre property sleeps eleven guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher and oven, free Wi-Fi, and a cosy fireplace.
8.9 24 reviews
Chesapeake Bay
29/08 – 05/09
237 €/nighttotal: 1659 € (7 )
Waterfront Reedville Home With Private Dock!
3 2
house , Heathsville
This waterfront property is situated in Reedville, a charming town just a short 107km drive from Heathsville and 108km from Newport News/Williamsburg International Airport. The house has received excellent ratings for cleanliness, location and user experience. The 3-bedroom home offers 140 square metres of living space, comfortably accommodating up to 6 guests. Enjoy direct access to the water via a private dock, a fully equipped kitchen, comfortable beds, towels and linen, free Wi-Fi, cable TV, and easy access to local attractions.
9.4 184 reviews
Chesapeake Bay
27/06 – 04/07
147 €/nighttotal: 1029 € (7 )
Barclay Towers Resort Direct Oceanfront Unit
1 3
resort , Virginia Beach
This one-bedroom apartment is located in the Barclay Towers Resort, just a short walk from Virginia Beach's bustling boardwalk and the sandy shores of the Atlantic Ocean. It has received excellent user and location ratings and a very good cleanliness rating. The apartment comfortably sleeps four guests and comes equipped with a full kitchen, allowing you to prepare meals during your stay. You'll also have access to a range of resort amenities, including a swimming pool, jacuzzi, fitness centre, and laundry facilities.
Chesapeake Bay
30/07 – 03/08
509 €/nighttotal: 2036 € (4 )
Lusby Beach House -3 Bd 2 Ba Steps To The Sand
3 10
house , Chesapeake Ranch Estates
This beachfront property in Lusby, within Chesapeake Ranch Estates, offers direct access to the sand and is located 10.5 kilometres from Annmarie Garden and 12.1 kilometres from Calvert Marine Museum. This 139 square metre residence provides three bedrooms, two bathrooms, and accommodation for fourteen guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, a private patio, garden access, and complimentary private parking.