10 Best Airbnb Vacation Rentals Near Chesapeake Bay, USA - Updated 2022

airbnb chesapeake bay

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.

1. Riverfront cottage in Lexington Park with ample facilities (from USD 90)

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.

Adorable Waterfront Apartment Weekend Getaway
Lexington Park, Maryland, United States
170 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
from the spectacular marble bathroom to the breathtaking view of the water it was a magical weekend
the views from the living room and natural light throughout add to the relaxing atmosphere
the best part of the apartment was the natural light with a breathtaking view of the sunset
gorgeous views of the water from the kitchen living room and dock
the sunsets were stunning even in winter and the apartment gets amazing afternoon sunshine
very clean & comfortable
everything was sparking clean and comfortable
everything was super clean and accessible
the apartment was spotless and comfortable
so clean everything—bed couch bathroom kitchen—smelled good and felt clean
helpful directions and dinner suggestions
great apartment and great host
theresa is a wonderful host
theresa and kevin are great hosts
i had a great stay host was wonderful
a wonderful place to get away
the space was immaculate and updated and the location is stunning
what a wonderful calm quiet few days despite a hurricane of all things blowing through in the middle
then there's the location and view-- right on the water with an amazing dock to hang out on
this place is a gem the location is wonderful and the cottage is so lovely- very tranquil and peaceful
Read more reviews

2. Stylish house in Leonardtown with fantastic bay views (from USD 157)

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.

Sandy Beach on Breton Bay with Beach
Leonardtown, Maryland, United States
142 reviews Superhost  Wifi Available
Entire residential home 4 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
peaceful wonderful amenities very comfortable beds
the view from the livingroom & dining room was amazing especially at sundown
the house is so quaint with gorgeous water views from the living room
the heater worked real well which was nice since our stay was in the winter
beds were super comfy and the kitchen was well-stocked
simple clean comfortable decor
the bathroom is nice and clean
very clean we loved it
the space was extremely clean and very comfortable
the house was clean
the host was great and helpful
host was super friendly and responsive all through the reservation process and our stay
the host has lots of thoughtful touches throughout the home and is easy to communicate with
ruth was an excellent host
she was friendly responsive and very accommodating
peaceful location that is very close to a cute town
a beautiful spot very close to dc
the location is awesome right on the water and near some great attractions within a short driving distance
also a great location to travel with a family
the neighbors are close by but we’re pleasant
Read more reviews

3. Inviting studio with great views of Chesapeake Beach (from USD 95)

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.

Minimalist art retreat AWESOME VIEWS location!
Chesapeake Beach, Maryland, United States
20 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
beautiful sunrise views from the apartment and short distance to the boardwalk and beach
the apartment was spacious with a nice living room dining area full kitchen full bathroom nice bedroom
the place has everything we need and is sparklingly clean
the hosts were wonderful and provided a safe fun and overall great environment
jacqueline is an incredible and kind host
jacqueline is an attentive and thoughtful host and i wholeheartedly recommend her place
the host is easy to reach and always respond to our question in seconds
great view and great host great for a couple's weekend getaway
this is a great location
amazing apartment that is close to the water and many fun activities
awesome people great location and perfect for a short getaway
a magnificent one bedroom apartment in a quiet quant and relaxing neighborhood
the apartment is a minimalist getaway in a peaceful location
Read more reviews

4. Snug cabana on a pier in Solomons (from USD 118)

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.

“Cabana by the Bay”-tiny home on a pier!
Solomons, Maryland, United States
294 reviews Superhost  Wifi Available
Tiny house 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the cottage is charming and comfortable with great peaceful views right on the water as described
great view and a nice kitchen area
we found the sofa bed to be very comfortable
very cozy and well-kept not to mention a fantastic view would love to stay again
tv and fireplace are very nice as is the living space and deck outside the front door
space was clean and well appointed
nice and clean and quiet)
the place was very clean and comfortable
extremely clean and breathtaking
this tiny house is so clean and bright
andrea is a great host
andrea was a great host who was very responsive
andrea is so communicative and lovely
andrea was very responsive and accommodating
lovely furnishing and conveniences and the host was very kind
cute restaurants within a 3 minute walk
its location is amazing
good location as well
also location was great as well
excellent escape near dc metro and n
Read more reviews

5. Spacious guesthouse in Crownsville surrounded by woods (from USD 124)

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.

The Kayak House
Crownsville, Maryland, United States
153 reviews  Wifi Available
Entire residential home 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the kitchen was fully equipped with everything we needed including a keurig for easy coffee
the bathroom was beautiful and kitchen amenities were plentiful
comfortable and functional space perfect for active travelers wanting to experience a little nature in coastal maryland
the beds and pillows were very soft which made sleeping really easy
quiet peaceful setting and spacious comfortable cottage
clean and cozy and quiet
the space is spotlessly clean
the house was clean cute and had everything we needed
very cute and stylish space it was very clean and the bed was super comfy
the place is spacious clean and had everything we needed for a long weekend
the host us very responsive
greg is a great host
place was great the hosts were very friendly
great spot to reserve even better hosts
greg was a wonderful host and very prompt with responding back
good location for local hikes
excellent house at a prime location
amazing area so close to washington
excellent location beautiful scenery and wonderfully private
this is a beautiful and comfortable home located in a great & safe location
Read more reviews

6. Relaxing cottage on Deal Island (from USD 125)

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.

Water View Cottage
58 reviews Superhost  Wifi Available
Entire cottage 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
great wifi too we probably had 6-8 devices on wifi and never had a speed issue
the cottage was comfortable and relaxing
really enjoyed the stunning sunsets from the florida room
beautiful views from many rooms in the house
this cottage is beautiful and comfortable for a couple or small family
highly recommend if you are looking for a relaxing clean and comfortable environment
the place is clean and bright and the location right next to the water cannot be beat
mo is a great host quick and responsive even to our stupid questions
host is great as well and very friendly
it is spacious comfortable and very close to the water
the neighborhood is quiet and peaceful and a perfect place to relax especially during quarantine time
we really enjoyed our stay and hope to come back to the quiet comfort again soon
this was a perfect place for a relaxing family vacation
a wonderful place to find peace and quiet
Read more reviews

7. Basement-level apartment in Great Mills with patio access (from USD 60)

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.

Furnished apt driving distance to Calvert Cliffs
Great Mills, Maryland, United States
11 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
everything was so clean and smelled amazing
apartment was clean and cozy having it's own thermostat
tom and denise were amazing hosts
host was very welcoming greeted me at my car and gave me a full tour of the flat
we were running late and they were very accommodating and helpful when we arrived
we were very pleased with the apartment and the location was good for us
Read more reviews

8. Compact cottage with private dock access in Saint Inigoes (from USD 72)

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.

Historic St.Mary's City at the Lazy Bear Cottage
Saint Inigoes, Maryland, United States
207 reviews Superhost
Tiny house 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
lovely to be able to roll out of bed and watch the sunrise on the water
space is well thought out and has all the comforts you need especially a nice bathroom
great view of the water cute porch to sit and have breakfast on quiet free parking clean
this is an awesome small place stylish interior a real tiny house cozy warm and with a great view
the place was clean and comfortable and the water views were spectacular
it was spotlessly clean
the place was very clean and cozy
the place is spotlessly clean
a clean cozy and quiet retreat from the world
it is clean and simple but built with comfort in mind
the hosts were incredibly gracious
the hosts are very hospitable and friendly
the hosts are extremely friendly and accommodating
nancy was a wonderful host
hosts checked in with us to make sure all was going well
great place in a great location
cozy little cabin in a great location
the location is perfect for taking it easy and exploring the area
the location is great for relaxing or exploring around the area
it's location is great since it is a short drive to state parks and beaches
Read more reviews

9. Waterfront cottage in Westover with private beach and dock (from USD 225)

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.

Heaven on the Bay - A Peaceful Waterfront Retreat
Westover, Maryland, United States
50 reviews Superhost  Wifi Available
Entire cottage 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
amazing views comfortable accommodations wonderful hosts
the kitchen is a beautiful space
plenty of great kitchen staples
place was clean and communication was fantastic
the house was so clean and such a unique space
clean and as pictured -- and right on the water
cozy and clean the perfect place to get away from it all even in the winter months
the hosts are super responsive and answer your questions almost immediately
the hosts were incredibly responsive and accommodated our early check in time
cheryl and elliot were wonderful hosts
i highly recommend reading the house manual because it was very helpful
the location was great and the house was thoughtfully decorated and comfortable
the location is easy to get to and mostly private perfect for our short stay
there was only 1 restaurant close by but it was delicious and a great outdoor environment
Read more reviews

10. 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.

Wright’s Cottage- No cleaning fees! Pets! River!
Annapolis, Maryland, United States
192 reviews
Entire house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
comfortable and quaint with complete privacy
it's a very cozy quaint cottage perfect size
cute cozy cottage - would definitely recommend
the cottage is extremely cozy and i loved the small touches inside and around the house
we really enjoyed our time at wright cottage - space was exactly as described cozy and cute
very clean and nice space
super clean and stylishly quaint
great place - clean and well appointed
it was extremely clean and tidy
super clean had a great time
owner was very responsive
helpful hosts who are quick to reply
darren and kristy are wonderful hosts
great hosts amazing house - couldn’t give a better recommendation
darren & kristy are very communicative and offer great hospitality
the location was great
such a cute place and a beautiful location
the location is awesome
cute place 10-15 minute drive from everything
and close enough to downtown to be within easy reach
Read more reviews

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!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Writing and travelling both bring joy to Sowmya's life. Her favourite destination so far is Bhutan. A land of incredible beauty! And her favourite style of travelling is solo backpacking!...Read more

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