Find short term rentals in Chesapeake Bay at the best prices
5791 available short term rental offers
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Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Chesapeake Bay
10 173 reviews
Chesapeake Bay
30/07 – 05/08
$478/nighttotal: $2868 (6 )
The Yellow Cottage On Harness Creek
2 6
cottage , Annapolis
The Yellow Cottage is located on Harness Creek in Hillsmere, a peaceful residential neighbourhood in Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming property has received excellent user ratings, making it a popular choice for travellers. The cottage offers 88 square metres of living space, comfortably accommodating up to six guests in two bedrooms and a living room with a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as activities such as fishing, crabbing, and kayaking on the creek.
9.4 20 reviews
Chesapeake Bay
29/08 – 05/09
$233/nighttotal: $1631 (7 )
Comfortable & Private 2 Bedrm Cottage W/ King Bed.
2 2
cottage , Portsmouth
This charming cottage is situated just 1.6 kilometres from Rivers Casino Portsmouth and Portsmouth City Park, making it a great base for exploring the city. It has received excellent reviews from previous guests. This cosy home has two bedrooms and a bathroom, covering 76 square metres, and can accommodate up to 5 guests. The property offers a fully equipped kitchen, a terrace, a garden, parking, free Wi-Fi, and a range of entertainment options.
9.4 16 reviews
Chesapeake Bay
30/07 – 05/08
$795/nighttotal: $4770 (6 )
Adorable Chesapeake Bay Beach Cottage B Just 1 Block From The Sand!
3 6
cottage , Virginia Beach
This charming three-bedroom cottage is located in Northeast Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, and within three miles of Chesapeake Beach and Sylvan Beach. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient location. The 167 square metre cottage comfortably sleeps six guests and offers three bathrooms, a fully equipped kitchen, and a private water park. Guests can enjoy a range of amenities including a terrace, garden, spa, and parking, as well as access to free WiFi, a Smart TV, and a washing machine.
9.9 249 reviews
Chesapeake Bay
20/07 – 27/07
$199/nighttotal: $1393 (7 )
Hedgerow, Deer Haven In The Nnk- Dock & Boat Ramp
1 4
apartment , Lancaster
HedgeRow is a charming cottage situated just 10 kilometres from Kilmarnock, on the Great Wicomico River in Virginia. The cottage enjoys excellent user, location and cleanliness ratings, making it a popular choice for travellers seeking a peaceful getaway. The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a fully-equipped kitchen, a private patio, a sandy beach, and access to two kayaks and a paddleboard.
9.8 315 reviews
Chesapeake Bay
23/08 – 28/08
$239/nighttotal: $1195 (5 )
The Heron's Nest At Atlantic Marina
1 2
cottage , Lake Shore
This charming lakeside retreat is located in Pasadena, Maryland, just a short drive from historical landmarks and art galleries. It has received excellent reviews from previous guests. The cottage offers 54 square metres of living space, accommodating up to four guests in a comfortable layout with one bedroom and one bathroom. You can enjoy a range of amenities including a swimming pool, a terrace, and a garden, and the property is perfect for enjoying water activities like fishing and boating.
9.9 76 reviews
Chesapeake Bay
01/10 – 05/10
$289/nighttotal: $1156 (4 )
Summer Breeze Waterfront New Home-private Beach
1 3
apartment , Kilmarnock
Summer Breeze, a three-bedroom waterfront house in Reedville, offers private beach access and is situated 30.6km from Kilmarnock, close to the Reedville Fisherman's Museum. This self-catering property sleeps six, boasts a private pier, canoe, screened porch, and access to a neighbourhood boat ramp, plus a dishwasher, fridge, freezer, microwave, air conditioning, Wi-Fi, and parking.
9.2 180 reviews
Chesapeake Bay
01/10 – 05/10
$378/nighttotal: $1512 (4 )
Beachside Retreat For 4 Walk To Buckroe Beach!
2 3
apartment , Hampton
This two-bedroom flat is located just 0.4 kilometres from Buckroe Beach, offering easy access to the sand and surf. The apartment is highly rated, with excellent user, location and cleanliness scores. The flat can comfortably accommodate up to four guests and is equipped with a range of amenities, including a private garden, a terrace, a jacuzzi, a fully equipped kitchen, and a washer and dryer. Guests can enjoy complimentary Wi-Fi, relax in the garden, and take advantage of the close proximity to the beach, playground, and bathhouse.
9.3 135 reviews
Chesapeake Bay
01/10 – 05/10
$307/nighttotal: $1228 (4 )
️Ice Ice Baby️downtown Newport News!
1 3
apartment , Newport News
This smoke-free flat is conveniently located in Newport News, just a short walk from City Hall and within easy reach of The Newsome House Museum and Cultural Center, King-Lincoln Park, and other attractions. It has received excellent ratings for its location, cleanliness, and overall user experience. The one-bedroom flat comfortably sleeps four guests and features a well-equipped kitchen, a washing machine, a sofa bed, and a TV. It also offers amenities such as a hair dryer, an iron/ironing board, and a desk, along with parking for guests travelling by car.
10 18 reviews
Chesapeake Bay
29/08 – 05/09
$241/nighttotal: $1687 (7 )
Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches
2 2
cottage , New Church
Serenity Cottage, a two-bedroom self-catering property near Pocomoke City, Maryland, offers easy access (within a few kilometres) to Pocomoke River State Park and the Delmarva Discovery Museum. This octagonal house sleeps five, features a fully equipped kitchen with vintage touches, a unique second-floor cupola room, and allows pets; nearby activities include kayaking, canoeing, hiking, and exploring historical towns on the Eastern Shore.
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.
8.7 249 reviews
Chesapeake Bay
23/08 – 28/08
$173/nighttotal: $865 (5 )
Elk Forge Bed And Breakfast
1 2
B&B , Elkton
This Elkton bed and breakfast is located just six miles from the University of Delaware and a short drive from Newark, Delaware, offering a peaceful retreat away from the city. It has consistently received very good ratings for its location, cleanliness, and overall experience. The property features spacious rooms, each with a unique design, a sitting area, and a fireplace. Guests can enjoy a range of amenities including a spa with a hot tub, a gourmet breakfast, barbecue facilities, and a business centre.
9.8 123 reviews
Chesapeake Bay
23/08 – 28/08
$227/nighttotal: $1135 (5 )
Guesthouse In Ideal Location With Private Entrance
1 2
apartment , Suffolk
This Suffolk apartment is conveniently located within 5km of Riverfront Golf Club and local medical facilities, including Bon Secours Health Center At Harbour View and Sentara BelleHarbour, and within 14km of Chesapeake Square Mall and Portsmouth City Park. This self-catering flat offers one bedroom, one bathroom, sleeping up to two guests, and features free Wi-Fi, a Smart TV, in-unit laundry, and convenient on-site parking.
Best family friendly Chesapeake Bay Short term rentals
Among the 5791 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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.
Frequently Asked Questions about short term rentals in Chesapeake Bay
What are the best short term rentals in Chesapeake Bay?
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.
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.
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.
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
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.
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.
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.
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.