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

Unique Tangier Cottage W/ Chesapeake Bay Views! - Chesapeake Bay
10 14 reviews
Chesapeake Bay
29/08 – 05/09
$389/nighttotal: $2723 (7 )

Unique Tangier Cottage W/ Chesapeake Bay Views!

4 2
cottage , Tangier
This family-friendly Tangier holiday home is situated less than 1 kilometre from both the Tangier Museum of History and Tangier Island Beach.
The 167 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, terrace, garden, parking, and Wi-Fi.
Coastal Charmer - Chesapeake Properties - Chesapeake Bay
9.6 58 reviews
Chesapeake Bay
27/06 – 04/07
$881/nighttotal: $6167 (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.
Exceptional North End Vb Condo - Chesapeake Bay
10 2 reviews
Chesapeake Bay
27/06 – 04/07
$416/nighttotal: $2912 (7 )

Exceptional North End Vb Condo

1 3
apartment , Virginia Beach
This two-bedroom, two-bathroom apartment in Virginia Beach's tranquil North End offers direct beach access across the street and is within walking or cycling distance of restaurants such as Atlantic on Pacific and attractions including the Virginia Aquarium.
The renovated condo sleeps six, features a fully equipped kitchen with a large island, a private patio with barbecue overlooking a communal pool, two dedicated parking spaces, and keyless entry; nearby activities include Ocean Breeze Waterpark.
New Bathrooms For 2026! Big Community Pool. Vb North End, Steps From Beach. - Chesapeake Bay
10 62 reviews
Chesapeake Bay
27/06 – 04/07
$472/nighttotal: $3304 (7 )

New Bathrooms For 2026! Big Community Pool. Vb North End, Steps From Beach.

2 3
apartment , Virginia Beach
This Virginia Beach condo is situated less than 1.6km from First Landing State Park and the Virginia Beach Boardwalk, offering easy access to the beach and local attractions.
The 84 square metre apartment sleeps six guests, boasting two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, a terrace, and access to a swimming pool, spa, and on-site water park.

Best Chesapeake Bay lodging with a balcony

Rooftop Pool & Lounge In Downtown Charm Free Indoor Parking - Chesapeake Bay
Chesapeake Bay
23/08 – 28/08
$228/nighttotal: $1140 (5 )

Rooftop Pool & Lounge In Downtown Charm Free Indoor Parking

1 2
apartment , Baltimore
This downtown Baltimore flat offers a prime location, situated within walking distance of the Inner Harbour, Baltimore Convention Centre, and Power Plant, with Baltimore-Washington International Airport approximately 14 kilometres away.
This residence provides a rooftop pool with city views, complimentary indoor and private parking, a fitness centre, spa facilities, and a 24-hour front desk, alongside full kitchen amenities and free WiFi.
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.
Oceanfront 2 Bedroom, 2.5 Bath Condo Overlooking The Boardwalk - Chesapeake Bay
9.6 119 reviews
Chesapeake Bay
27/06 – 04/07
$676/nighttotal: $4732 (7 )

Oceanfront 2 Bedroom, 2.5 Bath Condo Overlooking The Boardwalk

2 3
apartment , Virginia Beach
This oceanfront condo in Northeast Virginia Beach, situated between 21st and 22nd Streets, offers direct boardwalk and beach access, proximity to the Veterans United Home Loans Amphitheatre and other attractions.
The 116 square metre (1248 square foot) apartment boasts two bedrooms, three bathrooms, sleeping up to six guests, and features a fully equipped kitchen, a balcony with stunning ocean views, a fitness centre, swimming pool, tennis court and free Wi-Fi.
Summerlee At Scotland Yards - Chesapeake Bay
9.8 109 reviews
Chesapeake Bay
27/06 – 04/07
$941/nighttotal: $6587 (7 )

Summerlee At Scotland Yards

5 3
apartment , Piney Point
This villa-styled chateau in the rural beach area of Point Lookout, Scotland, Maryland, offers direct beach access and is located 1.1 kilometers from Confederate Memorial Park and 3.5 kilometers from Historic St. Mary's City.
This 256 square meter apartment, suitable for 10 guests, features 5 bedrooms, 5 bathrooms, a kitchen equipped for entertaining with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, parking, and wood-burning fireplace, with two kayaks available for use from late spring to early fall.

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Best Chesapeake Bay lodging with a kitchen

Private Yard & Water Views: Cozy Urbanna Cottage - Chesapeake Bay
10 21 reviews
Chesapeake Bay
30/07 – 05/08
$479/nighttotal: $2874 (6 )

Private Yard & Water Views: Cozy Urbanna Cottage

3 6
cottage , Urbanna
This family-friendly cottage is located in Urbanna, just 8.4 kilometres from the Middlesex County Museum and within 32 kilometres of several other attractions including the Steamboat Era Museum and Deltaville Maritime Museum. The cottage is highly rated by previous guests and enjoys a peaceful setting.
The 139 square metre cottage has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It offers a well-equipped kitchen, a garden, a patio, barbecue facilities, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
A Piece Of Paradise - Chesapeake Bay
9.9 219 reviews
Chesapeake Bay
01/10 – 05/10
$156/nighttotal: $624 (4 )

A Piece Of Paradise

1 3
apartment , Nanticoke Acres
This Nanticoke Acres guesthouse is situated minutes from Roaring Point Park and Nanticoke Harbour, approximately 48 kilometres from Salisbury.
The self-catering property offers two bedrooms, one bathroom, sleeping up to six guests, and features a private entrance, waterfront access for kayaks and paddleboards, a kitchenette, continental breakfast, and an outdoor gas grill.
Charming 3 Br North End Beach Cottage One Block To The Beach - Private Parking + Private Backyard - Chesapeake Bay
9.8 53 reviews
Chesapeake Bay
30/07 – 05/08
$1286/nighttotal: $7716 (6 )

Charming 3 Br North End Beach Cottage One Block To The Beach - Private Parking + Private Backyard

3 6
cottage , Virginia Beach
This charming cottage is located in Northeast Virginia Beach, just a short walk from First Landing State Park and the Virginia Beach Boardwalk. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage has three bedrooms and can comfortably sleep up to six guests, offering a spacious and comfortable retreat. It comes equipped with a range of features including a fully equipped kitchen, a swimming pool, a spa, and a garden, making it perfect for families and groups seeking a relaxing and enjoyable stay.
Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly) - Chesapeake Bay
10 16 reviews
Chesapeake Bay
30/07 – 05/08
$684/nighttotal: $4104 (6 )

Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly)

2 6
cottage , Madison
This charming waterfront cottage is located just a short drive from the historic town of Cambridge, Maryland, offering a peaceful escape from the bustle of Madison. The nearby Blackwater National Wildlife Refuge provides ample opportunities for nature lovers to explore.
The cottage features two bedrooms, comfortably accommodating up to six guests, and a fully equipped kitchen with modern appliances. Guests can enjoy the private dock, kayaks, and scenic views, or relax by the fire pit, unwind on the porch or deck, and take advantage of the spa and other amenities.

Best Chesapeake Bay lodging with laundry available

Cozy Modern Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 22 reviews
Chesapeake Bay
23/08 – 28/08
$245/nighttotal: $1225 (5 )

Cozy Modern Apt In The Heart Of Fells Point!

2 2
apartment , Baltimore
This Fells Point apartment in Baltimore is situated a short 1.8km walk from Harbour East Marina and within 3.2km of the Baltimore Convention Center and The Walters Art Museum.
This 60 square metre flat offers two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with dishwasher, in-unit laundry, and free Wi-Fi.
Artistic Environment Inspiring Home - Chesapeake Bay
9.8 71 reviews
Chesapeake Bay
27/06 – 04/07
$312/nighttotal: $2184 (7 )

Artistic Environment Inspiring Home

3 3
apartment , Kilmarnock
This spacious house, located in the Balls Neck area of Virginia's Northern Neck, is approximately 13 kilometres from Kilmarnock and within 3 kilometres of two Chesapeake Bay state parks.
Offering over 1800 sq ft of space, this three-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, laundry facilities, double panoramic decks, and access to a nine-acre plot with abundant wildlife viewing opportunities.
Cozy Modern Micro Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 33 reviews
Chesapeake Bay
23/08 – 28/08
$220/nighttotal: $1100 (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.
Monthly Discount- Beautiful House, Gloucester Va - Chesapeake Bay
10 30 reviews
Chesapeake Bay
23/08 – 28/08
$238/nighttotal: $1190 (5 )

Monthly Discount- Beautiful House, Gloucester Va

3 2
apartment , Deltaville
This recently refurbished property is situated in Gloucester, Virginia, just off the Piankatank River, and is within easy driving distance of Mathews Courthouse, Gloucester Main Street Community, Urbanna, and Gwynns Island. The house has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The 93-square-metre house has three bedrooms, two bathrooms, and can comfortably accommodate six guests. This pet-friendly home offers a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, and parking.
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