Spread over 200 mi (322 km), Chesapeake Bay is the largest estuary located within the United States. Known for its scenic landscapes, amazing seafood, and charming towns and islands, the Chesapeake Bay region is an excellent option for anyone looking to spend a few days surrounded by natural beauty. Although the bay touches several states, it is largely encircled by Maryland and Virginia. Some popular and charming locales to explore in Maryland are Annapolis, St. Mary’s City, Chesapeake Beach, and St. Michaels. In Virginia, the best places to check out include Cape Charles, Norfolk, Portsmouth and Virginia Beach. If you are looking for stay options for your trip, then read on for the best Airbnb vacation rentals near Chesapeake Bay, USA.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on August 31, 2025.
1. Riverfront cottage in Lexington Park with ample facilities (from USD 269)
Located right by St. Mary’s River, this pleasantly furnished waterfront cottage offers plentiful amenities. The one-bedroom apartment can host up to two guests and features a living room with a magnificent river view, a fully equipped kitchen with a skylight, and a bedroom with a double bed. Other facilities include a plush marble bathroom and a large waterfront deck with comfortable outdoor furniture and a grill. There is also an outdoor shower that guests can use to rinse off any remnants of the outdoors. Guests can make use of a nearby dock as well.
Lexington Park, Maryland, United States
21.85 km (13.6 mi) from Calvert Cliffs State ParkSuperhost
Accommodates: 2
Top guest reviews
Host:
helpful directions and dinner suggestionsgreat apartment and great hosttheresa is a wonderful hosttheresa and kevin are great hostsi had a great stay host was wonderfulLocation:
a wonderful place to get awaythe space was immaculate and updated and the location is stunningwhat a wonderful calm quiet few days despite a hurricane of all things blowing through in the middlethen there's the location and view-- right on the water with an amazing dock to hang out onthis place is a gem the location is wonderful and the cottage is so lovely- very tranquil and peacefulCleanliness:
very clean & comfortableeverything was sparking clean and comfortableeverything was super clean and accessiblethe apartment was spotless and comfortableso clean everything—bed couch bathroom kitchen—smelled good and felt cleanRead more reviewsAmenities & Room:
from the spectacular marble bathroom to the breathtaking view of the water it was a magical weekendthe views from the living room and natural light throughout add to the relaxing atmospherethe best part of the apartment was the natural light with a breathtaking view of the sunsetgorgeous views of the water from the kitchen living room and dockthe sunsets were stunning even in winter and the apartment gets amazing afternoon sunshine
2. Inviting studio with great views of Chesapeake Beach (from USD 646)
Bright, airy, and minimalist, this small studio located within a beach community is the perfect retreat for couples looking for a restful getaway. Offering lovely views and easy access to the bay, this basement studio apartment on the ground level comes with one bedroom, a basic kitchenette, and a small living room with a couch. The house is a part of the hosts’ house but it comes with a private side entrance.
Chesapeake Beach, Maryland, United States
33.7 km (21.0 mi) from Calvert Cliffs State ParkAccommodates: 2
Top guest reviews
Host:
the hosts were wonderful and provided a safe fun and overall great environmentjacqueline is an incredible and kind hostjacqueline is an attentive and thoughtful host and i wholeheartedly recommend her placethe host is easy to reach and always respond to our question in secondsgreat view and great host great for a couple's weekend getawayLocation:
this is a great locationamazing apartment that is close to the water and many fun activitiesawesome people great location and perfect for a short getawaya magnificent one bedroom apartment in a quiet quant and relaxing neighborhoodthe apartment is a minimalist getaway in a peaceful locationCleanliness:
the place has everything we need and is sparklingly cleanRead more reviewsAmenities & Room:
beautiful sunrise views from the apartment and short distance to the boardwalk and beachthe apartment was spacious with a nice living room dining area full kitchen full bathroom nice bedroom
3. Snug cabana on a pier in Solomons (from USD 257)
This newly renovated cabana is located right on a pier, which offers you unbeatable access and incredible views. Located in Solomons, the rental is a wonderful option for a couple’s getaway. The open-plan studio comes with a sofa bed that can sleep two, a kitchenette with basic equipment, and chairs. A small deck is available outside for you to relax. It also contains an outdoor shower. Guests can use the hosts’ private pier and rooftop deck and access the beach nearby.
Solomons, Maryland, United States
8.8 km (5.5 mi) from Calvert Cliffs State ParkAccommodates: 2
Top guest reviews
Host:
andrea is a great hostandrea was a great host who was very responsiveandrea is so communicative and lovelyandrea was very responsive and accommodatinglovely furnishing and conveniences and the host was very kindLocation:
its location is amazingcute restaurants within a 3 minute walkgood location as wellalso location was great as wellexcellent escape near dc metro and nCleanliness:
space was clean and well appointednice and clean and quiet)the place was very clean and comfortableextremely clean and breathtakingthis tiny house is so clean and brightRead more reviewsAmenities & Room:
the cottage is charming and comfortable with great peaceful views right on the water as describedgreat view and a nice kitchen areawe found the sofa bed to be very comfortablevery cozy and well-kept not to mention a fantastic view would love to stay againtv and fireplace are very nice as is the living space and deck outside the front door
4. Spacious guesthouse in Crownsville surrounded by woods (from USD 3095)
Located in Crownsville, this guesthouse is a converted barn spread over two levels. It is capable of sleeping up to four persons. The lower floor features an open-plan layout that includes a small kitchen, a living area with TV and electric fire, and a dining section with garden views. The adjoining yard overlooks woodlands and has a deck fitted up with outdoor furniture and barbecue equipment. A protected woodland across the street offers trails that can be explored.
Crownsville, Maryland, United States
74.64 km (46.4 mi) from Calvert Cliffs State ParkAccommodates: 4
Top guest reviews
Host:
the host us very responsivegreg is a great hostplace was great the hosts were very friendlygreat spot to reserve even better hostsgreg was a wonderful host and very prompt with responding backLocation:
good location for local hikesexcellent house at a prime locationamazing area so close to washingtonexcellent location beautiful scenery and wonderfully privatethis is a beautiful and comfortable home located in a great & safe locationCleanliness:
clean and cozy and quietthe space is spotlessly cleanthe house was clean cute and had everything we neededvery cute and stylish space it was very clean and the bed was super comfythe place is spacious clean and had everything we needed for a long weekendRead more reviewsAmenities & Room:
the kitchen was fully equipped with everything we needed including a keurig for easy coffeethe bathroom was beautiful and kitchen amenities were plentifulcomfortable and functional space perfect for active travelers wanting to experience a little nature in coastal marylandthe beds and pillows were very soft which made sleeping really easyquiet peaceful setting and spacious comfortable cottage
5. Relaxing cottage on Deal Island (from USD 523)
Enjoy the relaxing vibe of this cosy cottage that is located amid woods in Deal Island. The homely cottage comes with a living room, a full kitchen, and two bedrooms that can accommodate up to five guests. A deck and a front yard with patio furniture are available. Those are the perfect spots to enjoy amazing sunsets. Guests also have use of a nearby shared pier.
Deal Island, Maryland, United States
49.24 km (30.6 mi) from Calvert Cliffs State ParkAccommodates: 5
Top guest reviews
Host:
mo is a great host quick and responsive even to our stupid questionshost is great as well and very friendlyLocation:
it is spacious comfortable and very close to the waterthe neighborhood is quiet and peaceful and a perfect place to relax especially during quarantine timewe really enjoyed our stay and hope to come back to the quiet comfort again soonthis was a perfect place for a relaxing family vacationa wonderful place to find peace and quietCleanliness:
highly recommend if you are looking for a relaxing clean and comfortable environmentthe place is clean and bright and the location right next to the water cannot be beatRead more reviewsAmenities & Room:
great wifi too we probably had 6-8 devices on wifi and never had a speed issuethe cottage was comfortable and relaxingreally enjoyed the stunning sunsets from the florida roombeautiful views from many rooms in the housethis cottage is beautiful and comfortable for a couple or small family
6. Basement-level apartment in Great Mills with patio access (from USD 152)
This basement apartment has a private entrance and can host up to two guests. Neatly furnished, the apartment includes a full kitchen, a dinette area, and a comfortable living room with a TV. Guests have access to the front patio that has been fitted with barbeque equipment and seating, perfect for lounging around while watching the sunset. The apartment is close to St. Mary’s City.
Great Mills Corridor, Maryland, United States
14.07 km (8.8 mi) from Calvert Cliffs State ParkAccommodates: 2
Top guest reviews
Host:
tom and denise were amazing hostshost was very welcoming greeted me at my car and gave me a full tour of the flatwe were running late and they were very accommodating and helpful when we arrivedLocation:
we were very pleased with the apartment and the location was good for usRead more reviewsCleanliness:
everything was so clean and smelled amazingapartment was clean and cozy having it's own thermostat
7. Compact cottage with private dock access in Saint Inigoes (from USD 178)
This tiny house set by a river offers a wonderful setting for a peaceful vacation. The one-bedroom guest house is located away from the main house, which provides complete privacy. Inside, you will find an open-concept plan that includes a kitchenette and a dining area in addition to the bedroom. The highlight is the riverfront private wooden deck available for the exclusive use of the guests, which comes fitted with chairs and a picnic bench. Two more piers are available for guests’ use.
Saint Inigoes, Maryland, United States
26.78 km (16.7 mi) from Calvert Cliffs State ParkAccommodates: 2
Top guest reviews
Host:
the hosts were incredibly graciousthe hosts are very hospitable and friendlythe hosts are extremely friendly and accommodatingnancy was a wonderful hosthosts checked in with us to make sure all was going wellLocation:
great place in a great locationcozy little cabin in a great locationthe location is perfect for taking it easy and exploring the areathe location is great for relaxing or exploring around the areait's location is great since it is a short drive to state parks and beachesCleanliness:
it was spotlessly cleanthe place was very clean and cozythe place is spotlessly cleana clean cozy and quiet retreat from the worldit is clean and simple but built with comfort in mindRead more reviewsAmenities & Room:
lovely to be able to roll out of bed and watch the sunrise on the waterspace is well thought out and has all the comforts you need especially a nice bathroomgreat view of the water cute porch to sit and have breakfast on quiet free parking cleanthis is an awesome small place stylish interior a real tiny house cozy warm and with a great viewthe place was clean and comfortable and the water views were spectacular
8. Waterfront cottage in Westover with private beach and dock
Located on Eastern Shore of Maryland, this waterfront cottage offers direct access to the bay, including a beach and a dock. Guest staying here can also look at awesome bay views throughout the cottage, which can sleep up to six guests. It offers a well-planned layout that includes an attractively furnished living room, a fully equipped kitchen with the latest appliances, a dining area with bay views, and two bedrooms. One of the bedrooms comes with a balcony that also offers scenic views.
Westover, Maryland, United States
59.82 km (37.2 mi) from Calvert Cliffs State ParkAccommodates: 6
Top guest reviews
Host:
the hosts are super responsive and answer your questions almost immediatelythe hosts were incredibly responsive and accommodated our early check in timecheryl and elliot were wonderful hostsi highly recommend reading the house manual because it was very helpfulLocation:
the location was great and the house was thoughtfully decorated and comfortablethe location is easy to get to and mostly private perfect for our short staythere was only 1 restaurant close by but it was delicious and a great outdoor environmentCleanliness:
place was clean and communication was fantasticthe house was so clean and such a unique spaceclean and as pictured -- and right on the watercozy and clean the perfect place to get away from it all even in the winter monthsRead more reviewsAmenities & Room:
amazing views comfortable accommodations wonderful hoststhe kitchen is a beautiful spaceplenty of great kitchen staples
9. Bright, cheery cottage near Annapolis
This small cottage with a vintage charm is located within the grounds of a house in a community close to South River. The compact cottage can sleep up to two persons. Inside, guests will find a living room featuring wooden interiors, a full kitchen, and an elegantly decorated bedroom. Guests can access the shared gazebo and boat ramp that is located a short distance away. Though located outside the city, downtown Annapolis is just a 10-minute drive away.
Annapolis, Maryland, United States
65.02 km (40.4 mi) from Calvert Cliffs State ParkAccommodates: 2
Top guest reviews
Host:
owner was very responsivehelpful hosts who are quick to replydarren and kristy are wonderful hostsgreat hosts amazing house - couldn’t give a better recommendationdarren & kristy are very communicative and offer great hospitalityLocation:
such a cute place and a beautiful locationthe location was greatthe location is awesomecute place 10-15 minute drive from everythingand close enough to downtown to be within easy reachCleanliness:
very clean and nice spacesuper clean and stylishly quaintgreat place - clean and well appointedit was extremely clean and tidysuper clean had a great timeRead more reviewsAmenities & Room:
comfortable and quaint with complete privacyit's a very cozy quaint cottage perfect sizecute cozy cottage - would definitely recommendthe cottage is extremely cozy and i loved the small touches inside and around the housewe really enjoyed our time at wright cottage - space was exactly as described cozy and cute
10. Stylish house in Leonardtown with fantastic bay views
Switch off and enjoy a retreat in this waterfront cottage located in Leonardtown. The spacious house has three bedrooms which are capable of accommodating up to six guests. Tastefully decorated with classy furnishings, the house exudes a welcoming vibe. The open-plan layout includes a plush living area, a full kitchen, and a dining area. The interior lined with numerous windows offering great views. Outside the house, there is a comfortable deck overlooking the water, which is set up with outdoor furniture. Guests have access to a small dock and a sandy beach too.
Leonardtown, Maryland, United States
28.38 km (17.7 mi) from Calvert Cliffs State ParkAccommodates: 6
Top guest reviews
Host:
the host was great and helpfulhost was super friendly and responsive all through the reservation process and our staythe host has lots of thoughtful touches throughout the home and is easy to communicate withruth was an excellent hostshe was friendly responsive and very accommodatingLocation:
peaceful location that is very close to a cute towna beautiful spot very close to dcthe location is awesome right on the water and near some great attractions within a short driving distancealso a great location to travel with a familythe neighbors are close by but we’re pleasantCleanliness:
simple clean comfortable decorthe bathroom is nice and cleanvery clean we loved itthe space was extremely clean and very comfortablethe house was cleanRead more reviewsAmenities & Room:
peaceful wonderful amenities very comfortable bedsthe view from the livingroom & dining room was amazing especially at sundownthe house is so quaint with gorgeous water views from the living roomthe heater worked real well which was nice since our stay was in the winterbeds were super comfy and the kitchen was well-stocked
Take a break and have a a retreat in Chesapeake Bay
You can make your vacation to Chesapeake Bay an adventurous one that is filled with water activities such as boating, fishing, and kayaking. However, you also have the choice to just go on a soothing retreat. Whatever your plans are, you will find the perfect rental as the area offers numerous accommodations across all budgets. Our handpicked selection of the best Airbnb vacation rentals near the Chesapeake Bay, USA, is a great starting point, so pick one today!
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