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

The Little Blue Cottage - Topping : Waterfront! - Chesapeake Bay
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.
Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna - Chesapeake Bay
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.
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc. - Chesapeake Bay
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.
Coastal Charmer - Chesapeake Properties - Chesapeake Bay
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

Kingsmill Condo On Golf Course 9th Fairway! Local Owner - Chesapeake Bay
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.
Bohemia Manor Farm - Chesapeake Bay
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.
Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md - Chesapeake Bay
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.
Patuxent River View - Chesapeake Bay
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

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Best Chesapeake Bay holiday rentals with a balcony

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Chesapeake Bay
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.
Kings Creek Plantation By Tripforth - Chesapeake Bay
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.
Cabin At Holdens Creek On Eastern Shore Of Va - Chesapeake Bay
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.
Gaia House - Chesapeake Bay
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

Club Wyndham Kingsgate - Chesapeake Bay
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.
Cozy Fells Point Gem / In The Heart Of Fells Point - Chesapeake Bay
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.
Updated North Beach Cottage Pet Friendly! - Chesapeake Bay
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.
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Chesapeake Bay
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.
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