Find short term rentals in Chesapeake Bay at the best prices
5791 available short term rental offers
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Best Short term and Weekly rentals in Chesapeake Bay
9.7 235 reviews
Chesapeake Bay
27/06 – 04/07
$347/nighttotal: $2429 (7 )
Guest Quarters At The Inn - 205
1 3
apartment , North Beach
This one-bedroom flat is situated in Chesapeake Beach, just a short distance from the Bayside History Museum, Chesapeake Beach Water Park, and Rod n Reel Charter Fishing, offering easy access to the area's attractions. The property enjoys excellent user, location, and cleanliness ratings. The flat provides a comfortable living space with a fully equipped kitchen and a balcony for outdoor relaxation. Amenities include a swimming pool, a garden, and parking, as well as free Wi-Fi, air conditioning, and the option to bring pets.
9.2 11 reviews
Chesapeake Bay
30/07 – 05/08
$556/nighttotal: $3336 (6 )
Be Persuaded To Experience This Vintage Cottage By The Sassa
4 6
cottage , Galena
This charming cottage is located on the banks of a river, just 20 kilometres from attractions like Dutch Country Farmers Market, Betterton Beach, and Washington College. It has received excellent reviews from previous guests. This four-bedroom property comfortably sleeps eight guests and includes two bathrooms. The cottage offers a fully-equipped kitchen, a garden, barbecue facilities, a terrace, free Wi-Fi, and parking.
10 2 reviews
Chesapeake Bay
27/06 – 04/07
$300/nighttotal: $2100 (7 )
Walk To Patterson Park! Pet-friendly Townhome
2 3
apartment , Baltimore
This two-bedroom flat in Baltimore's Greektown district is located 3.2 kilometres from Canton Waterfront Park and 6.4 kilometres from the National Aquarium and Inner Harbour, with Camden Yards and M&T Bank Stadium 11.3 kilometres away. This 102 square metre property accommodates up to six guests and features a private patio, balcony, electric fireplace, and is equipped with free WiFi for remote working.
Chesapeake Bay
30/07 – 05/08
$592/nighttotal: $3552 (6 )
2 Bedroom Cottage At Coles Point Marina
2 6
cottage , Montross
This Montross cottage is situated in Hague, a 5-minute walk from Coles Point Marina and a 14-minute drive from The Hague Winery, with Sandy Point Beach 39 kilometres and Cedar Island 77 kilometres away. This 2-bedroom, 2-bathroom holiday home accommodates up to six guests, offering air conditioning, internet, and a dryer, with nearby access to Kinsale Museum, Westmoreland County Museum, Saint Mary's Fairground, and Michael P. O'Brien Athletics and Recreation Center.
9.5 2 reviews
Chesapeake Bay
27/06 – 04/07
$262/nighttotal: $1834 (7 )
Downtown And Inner Harbor Apartment
1 3
apartment , Baltimore
This one-bedroom flat offers a prime downtown Baltimore location, just a 6-minute walk to the Sports Legends Museum at Camden Yards and 0.8 kilometres from the University of Maryland – Baltimore, with Carroll Park, Power Plant, the Walters Art Museum, and Pier Six Concert Pavilion also within 1.9 kilometres. This 53 square metre serviced apartment, which can accommodate up to five guests, features complimentary private parking, free Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and a private entrance for your convenience.
9.7 231 reviews
Chesapeake Bay
23/08 – 28/08
$223/nighttotal: $1115 (5 )
Charming Federal Hill! One Bedroom With Vibes
1 2
apartment , Baltimore
This smoke-free flat is located in Federal Hill, a short walk from Federal Hill Park and M&T Bank Stadium, offering a mix of historic charm and modern amenities. The property has received excellent ratings for location, cleanliness and overall experience. The apartment has one bedroom, one bathroom and can accommodate up to three guests. It features a fully equipped kitchen, a washer/dryer, a comfortable sofa bed, a Smart TV with Netflix and games for entertainment.
9.8 54 reviews
Chesapeake Bay
23/08 – 28/08
$295/nighttotal: $1475 (5 )
Shadowlawn Villas, Suite Ii
1 2
apartment , Virginia Beach
This one-bedroom apartment is situated in Northeast Virginia Beach, just a kilometre from Pacific Avenue and the Virginia Beach Boardwalk, and less than two kilometres from Sandbridge Beach and the Virginia Beach Fishing Pier. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The apartment is ideal for couples or solo travellers, and it features a fully equipped kitchen, a comfortable living space, and a private balcony. Guests can enjoy access to a swimming pool, a spa, and a garden, as well as free parking and Wi-Fi.
9.9 268 reviews
Chesapeake Bay
01/10 – 05/10
$189/nighttotal: $756 (4 )
Cozy Little Cottage
1 3
apartment , California
This two-bedroom cottage near Solomons Island, Maryland offers easy access to the boardwalk and is within a short distance (distances unspecified) of historical attractions, lighthouses, and opportunities for fishing, crabbing, and shark tooth hunting. The property features an open-plan layout suitable for families, sleeps four guests, and includes a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and excellent user ratings for cleanliness and location.
9.8 18 reviews
Chesapeake Bay
30/07 – 05/08
$613/nighttotal: $3678 (6 )
Charming 2-bedroom Cabin Close To Fair Hill On Horse Farm
2 6
cabin , Elkton
This Elk Neck lodge is situated near Elkton, Maryland, offering easy access to attractions such as the Elkton Golf and Batting Center and Fred Rust Ice Arena. Sleeping up to 13 guests, this two-bedroom, three-bathroom property features a queen, full, and twin beds, plus additional sleeping arrangements, three bathrooms (one with a jetted tub), and internet access; nearby activities include horse shows, marinas, Newark Shopping Centre, Castle Mall, Bob Carpenter Center, and New Castle 100 Archers.
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.
Chesapeake Bay
29/08 – 05/09
$273/nighttotal: $1911 (7 )
Waterfront Cottage In Mt. Vernon
2 2
cottage , Mount Vernon
This detached house is located in Princess Anne, offering convenient access to Cedar Hill Marina and Bordeleau Winery, with Mount Vernon Park and Mount Vernon Beach a short distance away. This property accommodates up to six guests across two bedrooms and one bathroom, featuring a fully equipped kitchen, a grill, complimentary WiFi, parking, and an expansive deck overlooking the Wicomico River, with an optional boat slip available for an additional charge.
10 511 reviews
Chesapeake Bay
29/08 – 05/09
$269/nighttotal: $1883 (7 )
Historic Cottage On Ware River Estate
1 2
cottage , Gloucester Courthouse
This charming cottage is situated on a picturesque river, just 8.7 kilometres from Riverside Walter Reed Hospital and 19.3 kilometres from Machicomoco State Park, offering a peaceful retreat for those seeking tranquility. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. The self-catering property has one bedroom and one bathroom, comfortably accommodating up to four guests. The cottage provides a range of amenities, including a fully equipped kitchen, a private patio, a hot tub, and a garden, offering everything you need for a relaxing and enjoyable getaway.
Best family friendly Chesapeake Bay Short term rentals
Among the 5791 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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.
Frequently Asked Questions about short term rentals in Chesapeake Bay
What are the best short term rentals in Chesapeake Bay?
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.
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.
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.
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
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.
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.
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.
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.