Holiday Rentals in Chesapeake Bay

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Chesapeake Bay holiday rentals
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6706 Holiday rentals and Airbnb in Chesapeake Bay

Best family friendly Chesapeake Bay holiday rentals

Among the 6706 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Chesapeake Bay
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.
Charming Annapolis Victorian - Chesapeake Bay
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.
Waterfront Baltimore 2br Furnished Apartment Apts - Chesapeake Bay
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.
102 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Chesapeake Bay
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

Kingsbay Dockside Waterfront House - Chesapeake Bay
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.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
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.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
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.
2br Former Bank Vault Tower · Inner Harbor Views - Chesapeake Bay
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

Destinations nearby

Best Chesapeake Bay holiday rentals with a balcony

Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer - Chesapeake Bay
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.
Water-view Deale Home Walk To Marina, Restaurants - Chesapeake Bay
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.
Suburban Comfort In Bowie! Apartment With Patio - Chesapeake Bay
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.
Unique Tangier Cottage With Chesapeake Bay Views! - Chesapeake Bay
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

Fish On-site Rappahannock River Gem! - Chesapeake Bay
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.
Waterfront Reedville Home With Private Dock! - Chesapeake Bay
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.
Barclay Towers Resort Direct Oceanfront Unit - Chesapeake Bay
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.
Lusby Beach House -3 Bd 2 Ba Steps To The Sand - Chesapeake Bay
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.
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