Find short term rentals in Chesapeake Bay at the best prices

5791 available short term rental offers

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Chesapeake Bay short term rentals
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Best Short term and Weekly rentals in Chesapeake Bay

Best family friendly Chesapeake Bay Short term rentals

Among the 5791 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Private Riverfront Home With Dock - Chesapeake Bay
9.0 4 reviews
Chesapeake Bay
20/07 – 27/07
$261/nighttotal: $1827 (7 )

Private Riverfront Home With Dock

3 4
apartment , Montross
This three-bedroom, two-bathroom apartment in Hague, Virginia, offers river access for kayaking and crabbing, and is situated approximately 48 kilometres from Westmoreland State Park and 64 kilometres from Colonial Beach.
Sleeping up to seven guests, this self-catering property boasts a private dock, fire pit, and is close to attractions including The Hague Winery and Menokin Foundation, with a fridge, microwave, dishwasher, air conditioning, terrace, garden and parking also provided.
Irvington Country Getaway House - Chesapeake Bay
10 155 reviews
Chesapeake Bay
20/07 – 27/07
$370/nighttotal: $2590 (7 )

Irvington Country Getaway House

3 4
apartment , Irvington
This property is situated in Irvington, just 0.3 kilometres from the Steamboat Era Museum and within 5 kilometres of Historic Christ Church and Compass Entertainment Complex, offering easy access to the town's attractions. This accommodation has received excellent ratings for location, cleanliness, and overall guest experience.
This three-bedroom house comfortably sleeps six guests, providing ample space for families or groups of friends. The property features a fully equipped kitchen, a private garden with barbecue facilities, and free Wi-Fi, making it ideal for both relaxation and entertainment.
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
$338/nighttotal: $2028 (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.
Relax And Renew On Your Private Deck Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 29 reviews
Chesapeake Bay
29/08 – 05/09
$227/nighttotal: $1589 (7 )

Relax And Renew On Your Private Deck Overlooking The Chesapeake Bay

2 2
cottage , Nassawadox
This charming cottage is located just a short drive from Northampton Shopping Centre and Holly Grove Vineyards, offering a peaceful retreat on the beautiful Nassawadox coastline. The property enjoys an excellent user rating, reflecting its comfortable and well-equipped nature.
This two-bedroom holiday home comfortably accommodates up to four guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, and a terrace with barbecue facilities, perfect for relaxing evenings or al fresco dining.

Best Chesapeake Bay lodging with a balcony

Cabin At Holdens Creek On Eastern Shore Of Va - Chesapeake Bay
9.8 187 reviews
Chesapeake Bay
01/10 – 05/10
$224/nighttotal: $896 (4 )

Cabin At Holdens Creek On Eastern Shore Of Va

1 3
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.
Baltimore Premier Townhouse - Chesapeake Bay
8.2 17 reviews
Chesapeake Bay
20/07 – 27/07
$243/nighttotal: $1701 (7 )

Baltimore Premier Townhouse

2 4
apartment , Baltimore
This Baltimore apartment, situated near Baltimore–Washington International Thurgood Marshall Airport (BWI), approximately 22.5 kilometres away, offers paid airport shuttle service.
The 929-square-metre property features two bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, garden, free Wi-Fi, barbecue facilities, and a patio with city views.
Sojourn's Harborage S - Chesapeake Bay
8.8 3 reviews
Chesapeake Bay
23/08 – 28/08
$283/nighttotal: $1415 (5 )

Sojourn's Harborage S

1 2
apartment , Norfolk
This Norfolk apartment, located in the desirable East Ocean View neighbourhood, is less than 0.6km from Norfolk Beaches and within a short drive of Ocean View Beach and Community Beach.
The 74 square metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private balcony, Wi-Fi, and on-site parking.
Pizza Friday - Chesapeake Bay
10 9 reviews
Chesapeake Bay
29/08 – 05/09
$663/nighttotal: $4641 (7 )

Pizza Friday

4 2
cabin , Piney Point
This Piney Point waterfront lodge is situated less than 1.6km from Cardinal Gibbons Park and First District Community Park, and approximately 4.8km from Saint Inigoes State Forest, offering stunning water views and direct water access.
Sleeping up to 10 guests, this four-bedroom, two-bathroom holiday home boasts a fully equipped kitchen, Smart TV, washing machine, fireplace, terrace, garden, barbecue, parking, and free Wi-Fi.

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Best Chesapeake Bay lodging with a kitchen

Beach Combing & Relaxation - Chesapeake Bay
9.7 100 reviews
Chesapeake Bay
01/10 – 05/10
$324/nighttotal: $1296 (4 )

Beach Combing & Relaxation

3 3
apartment , Calvert Beach
This apartment is located in a private community in Calvert Beach, Maryland, just a 1.6 kilometre walk from a beautiful stretch of beach. The apartment has excellent ratings for cleanliness, location and user experience.
The apartment has three bedrooms and one bathroom, covering 111 square metres and comfortably accommodating up to six guests. It features a fully equipped kitchen, a spacious deck with a fire pit, and a range of amenities for a relaxing beach getaway, including private beach access, a beach cart, and a high chair for families.
A Little Piece Of Paradise - Waterfront Home - Chesapeake Bay
9.9 89 reviews
Chesapeake Bay
20/07 – 27/07
$346/nighttotal: $2422 (7 )

A Little Piece Of Paradise - Waterfront Home

1 4
apartment , North Beach
This waterfront property in North Beach, Maryland, is situated less than 0.8 kilometres from the town centre and beach, offering uninterrupted Chesapeake Bay views.
This two-bedroom, two-bathroom holiday home sleeps six, boasting a fully equipped kitchen, private waterfront deck, and access to a fitness centre; kayaking is available nearby at Rose Haven Memorial Park, less than 1.6 kilometres away.
Cozy Home Away From Home Just Minutes From The Beach - Chesapeake Bay
9.7 177 reviews
Chesapeake Bay
01/10 – 05/10
$284/nighttotal: $1136 (4 )

Cozy Home Away From Home Just Minutes From The Beach

1 3
apartment , Virginia Beach
This one-bedroom apartment is located just 500 metres from Pacific Avenue and the Virginia Beach Boardwalk, with Sandbridge Beach and the Virginia Beach Fishing Pier within a 24 kilometre radius. It has been highly rated by previous guests, receiving excellent reviews for its location, cleanliness, and overall experience.
The apartment is 46 square metres in size and comfortably accommodates up to four guests. It comes equipped with a kitchen, a bathroom, a swimming pool, a spa, parking, and internet access, as well as a water park within the building.
Poe's Pad In Canton Quarters - Chesapeake Bay
9.2 10 reviews
Chesapeake Bay
23/08 – 28/08
$197/nighttotal: $985 (5 )

Poe's Pad In Canton Quarters

1 2
apartment , Baltimore
This Canton, Baltimore flat is ideally situated near Fells Point and major medical centres, offering easy access to Baltimore's Inner Harbour attractions.
The newly renovated one-bedroom apartment sleeps two, features a fully equipped kitchen with fridge and microwave, free WiFi, parking, and modern amenities including smart locks and air conditioning; guests can enjoy nearby sporting events at Oriole Park at Camden Yards and CFG Bank Arena.

Best Chesapeake Bay lodging with laundry available

Waterfront Maryland Retreat W/ Dock & Bay View! - Chesapeake Bay
9.8 10 reviews
Chesapeake Bay
30/07 – 05/08
$410/nighttotal: $2460 (6 )

Waterfront Maryland Retreat W/ Dock & Bay View!

3 6
cottage , Chance
This Chance waterfront holiday home is situated 2.6km from Shark Fin Shoal and 3.9km from Rock Island, within a 32km radius of Whitehaven Historic District and Mount Vernon Park.
The 201 square metre property boasts four bedrooms, two bathrooms, sleeps nine, and includes a fully equipped kitchen, laundry facilities, patio, barbecue, and parking.
Cozy Fells Point Gem / In The Heart Of Fells Point - Chesapeake Bay
9.8 479 reviews
Chesapeake Bay
23/08 – 28/08
$195/nighttotal: $975 (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.
Peaceful Getaway Convenient To Local Amenities Including Beach, Boating & Food - Chesapeake Bay
9.8 121 reviews
Chesapeake Bay
29/08 – 05/09
$353/nighttotal: $2471 (7 )

Peaceful Getaway Convenient To Local Amenities Including Beach, Boating & Food

2 2
cottage , Rock Hall
This charming cottage is located in Rock Hall, a historic fishing village on the Chesapeake Bay, within easy reach of Eastern Neck National Wildlife Refuge, Ferry Park, and the Waterman's Museum. It has consistently received excellent reviews from previous guests.
This two-bedroom, two-bathroom property offers 111 square metres of space, comfortably accommodating up to four guests. The cottage features a modern kitchen, a relaxing garden, and a spa, as well as access to local amenities, entertainment options, and a summer trolley service.
Entire Private 2 Bedrooms House, Nice Neighborhood - Chesapeake Bay
9.4 82 reviews
Chesapeake Bay
20/07 – 27/07
$320/nighttotal: $2240 (7 )

Entire Private 2 Bedrooms House, Nice Neighborhood

2 4
apartment , Arnold
This two-bedroom home is situated in Arnold, a peaceful neighbourhood just 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious apartment, spanning 111 square metres, comfortably accommodates up to 5 guests. Enjoy a range of amenities including a private hot tub, a peaceful garden, a fully equipped kitchen, air conditioning, free Wi-Fi and private parking.
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