Find short term rentals in Chesapeake Bay at the best prices

8364 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 8364 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Bay Creek (Pool!) Meets Historic Cape Charles! - Chesapeake Bay
9.9 119 reviews

Bay Creek (Pool!) Meets Historic Cape Charles!

apartment, Cape Charles
This three-bedroom apartment, located in the Marina East neighbourhood of the gated Bay Creek community, is just a short walk from the historic centre of Cape Charles and its many restaurants, shops, and attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 242 square metres and comfortably accommodates up to eight guests. It offers a range of amenities, including access to a private beach, a swimming pool, tennis courts, nature trails, and kayaks and paddle boards for exploring the nearby waters.
Egrets Point On The Creek - Chesapeake Bay
10 110 reviews

Egrets Point On The Creek

apartment, Onancock
Egrets Point on the Creek, a renovated mid-1950s ranch duplex in Onancock, offers a peaceful creekside setting close to the historic district and within easy reach of Chincoteague and Cape Charles.
This two-bedroom, one-bathroom property sleeps four, boasting a well-equipped kitchen, screened porch, sunporch, access to canoes, bicycles, and a golf cart (seasonal), a fire pit, and hammocks in the large garden; internet and air conditioning are also included.
Inn At Warner Hall - Chesapeake Bay
10 37 reviews

Inn At Warner Hall

B&B, Gloucester Point
The Inn at Warner Hall is a waterfront guesthouse situated in Gloucester Point, just 24 kilometres from historic Yorktown and 56 kilometres from Colonial Williamsburg. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The guesthouse is set on a 40-acre estate dating back to 1642, offering a unique glimpse into the region's history. Guests can enjoy a daily gourmet breakfast, relax in the gardens or on the porch, and take advantage of the boathouse for fishing or birdwatching.
Old Bay Bungalow - Chesapeake Bay
9.9 753 reviews

Old Bay Bungalow

B&B, Arnold
This private apartment is located in Arnold, just a short distance from Annapolis and a few blocks from the Magothy River, offering a peaceful retreat close to the water. It has received excellent ratings for cleanliness, location, and overall guest experience.
The self-contained apartment can comfortably accommodate up to four guests and features a separate entrance, a sunporch, a fireplace, and a fully equipped kitchenette. Guests can enjoy complimentary local microbrews, snacks, and other amenities, along with a charming interior and access to streaming services.

Best Chesapeake Bay lodging with a balcony

The Princess Anne 200 Inn At Old Beach - Chesapeake Bay
No reviews

The Princess Anne 200 Inn At Old Beach

B&B, Virginia Beach
B&B listing. This accommodation is based in Virginia Beach.
Services and facilities: a washing machine, a terrace and an iron. Enjoy free parking with this accommodation in Virginia Beach!
The Waverly 100 Inn At Old Beach - Chesapeake Bay
No reviews

The Waverly 100 Inn At Old Beach

B&B, Virginia Beach
B&B. You will be located in Virginia Beach.
Services and facilities include a fridge, a terrace and a washing machine.
Guest Quarters At The Inn - 205 - Chesapeake Bay
9.8 251 reviews

Guest Quarters At The Inn - 205

B&B
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.
Hilltop 104 Inn At Old Beach - Chesapeake Bay
No reviews

Hilltop 104 Inn At Old Beach

B&B, Virginia Beach
B&B rental. Your accommodation will be based in Virginia Beach.
Facilities and services: a fridge, a washing machine and an iron. Take advantage of the Free Parking with this accommodation in Virginia Beach!

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Best Chesapeake Bay lodging with a kitchen

Island Voices In The Wine Near Chincoteague & Nasa - Chesapeake Bay
9.9 47 reviews

Island Voices In The Wine Near Chincoteague & Nasa

apartment, Saxis
This recently renovated early 1920s two-storey flat offers a unique stay in a Saxis Waterman's fishing village, surrounded by water and adjacent to the Virginia Wildlife Refuge, placing it within a 15 kilometre drive of Chincoteague Island and Assateague Island, and a 30 kilometre drive from NASA Wallops Flight Facility.
This accommodation for four guests features two bedrooms and one bathroom, with air conditioning, Wi-Fi, a kitchen equipped with a fridge, freezer, and microwave, and offers access to a garden, parking, a fishing pier, and opportunities for kayaking and canoeing, with the beach just a short walk away.
Guest Suite For Up To 2 In A Victorian On The Chester River - Chesapeake Bay
9.8 23 reviews

Guest Suite For Up To 2 In A Victorian On The Chester River

apartment, Millington
This Millington apartment enjoys a riverside location, approximately 9.6km from Crumpton Park and Tilmon's Island Winery, and under 14.5km from Pinkney Park and Chase Island.
The one-bedroom, one-bathroom flat sleeps two guests and offers free Wi-Fi, a Smart TV, on-site parking, and a playground; in-unit amenities include a refrigerator, microwave, coffee/tea maker, and hair dryer.
Private Duplex Near Bwi Easy Access To I95 - Chesapeake Bay
9.3 4 reviews

Private Duplex Near Bwi Easy Access To I95

apartment, Linthicum
This private duplex is located in Linthicum Heights, Maryland, just 4 kilometres from Baltimore-Washington International Airport and within easy reach of I-95. The surrounding area is peaceful and family-friendly, offering a tranquil escape from the city.
This self-catering property comfortably sleeps up to 6 guests and is equipped with a fully fitted kitchen, private bathroom, flat-screen TV, air conditioning, and free Wi-Fi. Guests also benefit from free private parking and are within easy driving distance of attractions such as Carroll Park and the Sports Legends Museum at Camden Yards.
The Laughing King Retreat, Cedar Island Suite - Chesapeake Bay
10 1158 reviews

The Laughing King Retreat, Cedar Island Suite

B&B, Eastville
The Laughing King Retreat, an adults-only guesthouse, is situated on the Chesapeake Bay, a short drive from the Savage Neck Dunes Natural Wildlife Preserve.
This secluded waterfront farm offers a private pool, a dry sauna, a fire pit, a gazebo, a palapa, and a straw hat lending library, with the option to use the fully stocked gourmet kitchen.

Best Chesapeake Bay lodging with laundry available

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!! - Chesapeake Bay
9.2 29 reviews

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!!

apartment, Portsmouth
This Portsmouth townhouse, centrally located in Hampton Roads, offers easy access to the Rivers Casino (distance unspecified) and Virginia Beach Boardwalk (driving distance unspecified).
The 84-square-metre (904 sq ft) property sleeps four guests in two bedrooms with queen-size beds and smart TVs, and includes a fully equipped kitchen, private garden, parking, and excellent Wi-Fi.
1 Mi To Boardwalk: Convenient North Beach Apt! - Chesapeake Bay
8.0 1 review

1 Mi To Boardwalk: Convenient North Beach Apt!

apartment, North Beach
This North Beach flat, located approximately 1.6 kilometres from the North Beach Boardwalk, offers easy access to the Bayside History Museum and Chesapeake Beach Railway Museum.
The 46-square-metre self-catering apartment sleeps three, and includes a kitchen with fridge and microwave, laundry facilities, Wi-Fi, and a terrace; nearby attractions include the Chesapeake Beach Water Park and R&J's PlayPark.
Marvels On The Creek - Chesapeake Bay
9.9 239 reviews

Marvels On The Creek

B&B, Secretary
Marvels on the Creek is a charming bed and breakfast situated just 20 miles from the Academy of the Arts and 14 miles from Federalsburg Marina, offering a tranquil escape in the heart of Secretary. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The bed and breakfast features a single bedroom and bathroom, accommodating up to two guests. Amenities include a swimming pool, jacuzzi, spa, restaurant, room service, and a garden, providing a relaxing and luxurious experience.
Charming Barn In Annapolis For A Relaxing Getaway Not A Room Just A Mattress - Chesapeake Bay
No reviews

Charming Barn In Annapolis For A Relaxing Getaway Not A Room Just A Mattress

apartment, Annapolis
This one-bedroom flat is located in Annapolis's Historic District, offering a 1.08-kilometre walk to Navy-Marine Corps Memorial Stadium and a 1.17-kilometre walk to the Maryland State House.
The property provides air conditioning, in-unit laundry, and essential bathroom amenities, with the living room featuring a sofa bed, sheets, and an ironing board for your comfort.
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