The town of Chesapeake City in Cecil County, Maryland is a place filled with 19th-century homes and gardens that can be visited by going on a group or solo tour. There are tons of things to do in Chesapeake regardless of the season, such as going to the C&D Canal Museum and biking the Ben Cardin Recreational Trail. The major cities of Philadelphia and Baltimore are also just an hour drive away making it convenient for tourists to sightsee there as well. There is definitely no shortage of vacation rentals or hotels in Chesapeake City, so we listed the top Airbnb vacation rentals you could check out should you decide to visit this lovely town! Read on to find out more about the top Airbnb vacation rentals in Chesapeake City, Maryland.
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 April 06, 2024.
1. Apartment nestled in a late 19th-century historical gem
Nestled in a late 19th-century historical gem, this apartment in Chesapeake City melds tranquil antiquity with contemporary flair. A king-sized bed promises deep slumber in the cozy bedroom. In the compact kitchen, a toaster oven, microwave, and a midsize fridge await culinary adventures. The living space, complete with cable TV and Wi-Fi, opens doors to limitless streaming.
Guests are welcomed with an access code for hassle-free entry and can choose from street or under-bridge parking. While upstairs bustle may echo, it’s a quaint reminder of the home’s vintage soul, ideal for those who relish a tapestry of old-world charm and modern convenience.
Chesapeake City, Maryland, United States
8.95 km (5.6 mi) from Lums Pond State ParkSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
the refrigerator size was fine and there was an adorable ice maker on the kitchen tablethe rooms were perfect for the two of uswe were very comfortable and pleased with our stayvery comfortable bed and quiet bedroomCleanliness:
perfectly charming and very cleancharming clean and well keptvery clean and a comfy bedvery cozy and clean with a lot of special toucheseverything was super clean and we had everything we neededHost:
the owner amber was so accommodating and made us feel so welcome and she was so friendlyvery communicative host who had some great local suggestions charming place and town steventhe host amber is very responsive and pleasantamber was very responsive when i texted hervery well equipped comfortable and excellent communication from hostRead more reviewsLocation:
cute spot very convenient locationthe location was greatwonderful location walking distance to 8 restaurantsand the location is fantasticthe location was excellent with restaurants and shops within walking distance
2. Waterfront apartment blending historic charm with modern comforts (from USD 84)
Discover a tranquil retreat in Chesapeake City with this waterfront apartment, blending historic charm with modern comforts. This house for rent in Chesapeake City offers a peaceful environment with a plush queen bed and a snug sitting area. Equipped with a kitchen, Wi-Fi, and a 32-inch HDTV with streaming options, the apartment ensures a relaxed stay.
Step outside to a picturesque porch, ideal for sipping your morning brew, and savor the convenience of nearby cafes. Positioned ideally, it’s a short drive to major cities and the Delaware seashore. Outdoor paths and bike rentals nearby invite exploration along the scenic canal.
Chesapeake City, Maryland, United States
8.87 km (5.6 mi) from Lums Pond State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
comfy bed cozy sitting area full kitchen big bathroom peaceful chairs and little table out frontwe highly recommend cafe on the bay for morning coffees and breakfast sandwiches just steps from the apartmentgreat cozy place in a very cool historic small town) oh and the bed is very comfortable tooCleanliness:
it was very clean and karen gave detailed instructionsthe apartment was sparkling clean and had everything a guest could needthe apartment was extremely clean and had everything we neededthe apartment was very clean and all needed items were right at our fingertipshome was clean and had everything we neededHost:
the hosts were greathygge haven and our host karen were truly wonderfulkaren was an amazing hostvery responsive to questions/concernskaren and rick are great hosts and were very attentive with any questions we hadRead more reviewsLocation:
the location was perfectthe location was perfect for walking to nearby shops and restaurantsthis location has an excellent location and thoughtful amenitieswalking distance to everything easy check in and check outkaren's place is in an absolutely perfect location walkable to everything in just a super adorable little town
3. The Mint Cottage (from USD 396)
Nestled in Chesapeake City, a newly adorned cottage beckons, blending homey comforts with serene charm. Imagine a master bedroom, tranquil, with a plush king bed; a snug second room with a queen bed; and a third, adaptable, hosting a single and sofa bed. The cottage boasts a kitchen, replete with essentials, high-speed Wi-Fi, and central air. Entertainment? A TV awaits. Need to do laundry? Washer and dryer, complimentary.
Outside, a personal haven: a pool for cool plunges, a fire pit, and patio for peaceful evenings. Pets? Welcomed. Safety? Ensured with on-site cameras. Parking? Effortless, accommodating five vehicles.
Chesapeake City, Maryland, United States
9.25 km (5.8 mi) from Lums Pond State ParkAccommodates: 6
Top guest reviews
Amenities & Room:
the furnishings were beautiful and the cottage was well equipped and quite comfortable for a group of sixthe cottage was absolutely adorable and we enjoyed the poolperfect cottage for our weekend getaway beautiful furnishings comfy beds and great locationwe loved the private swimming pool fire pit and patio in the back yardwe had an amazing weekend at the mint cottage in chesapeake city the property was charming and cozyCleanliness:
very clean and elegant propertygreat clean place and nicely maintainedhouse was clean and nicely decoratedeverything was clean and gianmarco was very accommodatingadorable mint cottage was exactly as advertised clean and spaciousHost:
the host was kind and communicativethe host was very responsive to our questions and made our check in very easythe gianmarco’s were wonderful host quick to respond to any of our questionsthank you host for an amazing staygianmarco was the most gracious hostRead more reviewsLocation:
walking distance from restaurants and attractionsgreat location-about a 5 minute walk and you are in the cute town of chesapeake citygreat place with a cute themehouse location was perfect with a easy walk into town which we did frequentlyplus the location was perfect for strolling to the waterfront shops and restaurants
4. Coastal-themed cottage (from USD 123)
Enjoy the serene sights and sounds of Back Creek and passing ships in this one-bedroom, coastal-themed guest cottage. Built in the 1940s, this property used to be an exclusive cottage for preparing crab cakes for the local restaurant at the time.
The rental sports a courtyard, an eat-in kitchen, and coastal-glam decorations for your convenience and comfort. Just steps away from the home are Ben Cardin C&D Canal Trail and Michael Castle Trail which stretch for 17 mi (27 km).
Chesapeake City, Maryland, United States
8.59 km (5.4 mi) from Lums Pond State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
relaxing furniture to rest on with throw blankets to snuggle up in while watching cable tvwe enjoyed the coffee snacks and fresh flowers along with a comfy cozy living and bedroom spacewe loved everything about this cottage it is cozy stylish and comfortablewith its modern amenities and cozy feel we felt right at home cooking and relaxingwe loved staying at this cottage perfect location and very comfortable and wonderful amenitiesCleanliness:
clean and well maintainedvery clean and comfortablevery clean and stylish placesuper clean beautifully decoratedquiet clean and cozyHost:
amy is an outstanding host highly recommendthe decor was nice and the host was very accommodating and responsiveamy was very kind throughout the booking process and the stayour stay at the cottage was great the host went above and beyond what one would expectRead more reviewsLocation:
excellent location for a short breaklastly the location was greatperfect location near the canal and a short walk to a great seafood restaurantthe location is perfect for exploring chesapeake cityit is a great location close to the water walking trail restaurants all convenient
5. Relaxing guest suite in Brookbend
This charming Airbnb is a private bedroom perfect for couples, solo adventurers, or even working professionals travelling to Chesapeake. Furry friends are welcome as well! It has a nautical-themed interior and a private bath. A few kilometres away from the home is the historic town centre, sightseeing spots, restaurants and dining, family-friendly activities, as well as the beach. It is a truly a lovely place to stay in!
Elkton, Maryland, United States
10.46 km (6.5 mi) from Lums Pond State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
internet and cable tv were perfectthe view was amazing they were super accommodating and the room was perfectit was such a nice bonus to have a keurig with k-cups in our roomthe bed was super comfortable and the place was very roomyour guest room was spacious and stylish with a super comfy king size bed and en-suite bathroomCleanliness:
very clean and warm stayeverything is clean and lovelyeverything was spotless and we slept like babies in the comfy bedthe room and entire house is beautifully decorated and spotlessly cleansteven's place is absolutely spectacular super clean incredibly comfortable so beautifully decoratedHost:
steven and john are great hostssteven is pretty much the perfect hoststeven and john were great hostsawesome hosts and great hospitalitysteven and john are terrific hostsRead more reviewsLocation:
great place close to chesapeake citygreat location quiet and restfulvery quiet & relaxing location beautifully decoratedit's quiet and restfulconvenient for visits to better-known locations such as chesapeake city newark havre de grace etc
6. Lovely cottage suite in Brookbend
This charming one-bedroom cottage is situated just ten minutes away from Chesapeake City, as well as close to Baltimore and Philadelphia. Neatly decorated and well-equipped, the property also sits in a quiet neighbourhood 5 minutes off Interstate 95 in Elkton, MD. This lovely Airbnb has air-conditioning, cable TV, and wireless Internet connection available. So, if you are looking for an accommodation that is both welcoming and relaxing, then this might be the one for you.
Elkton, Maryland, United States
10.64 km (6.7 mi) from Lums Pond State ParkAccommodates: 2
Top guest reviews
Amenities & Room:
the views of the creek from their kitchen and porch are an added bonusthe decoration is classy but not pretentious throughout the house - the sunroom and kitchen views are amazingthe bed is very comfortable the view from the back beautiful with a gorgeous porch to enjoy iti wish i could have stayed longer quiet neighborhood beautiful views very comfortable housethe room was immaculate with some extra perks like chocolates and hi tech remoteCleanliness:
very clean and beautiful settingvery clean and beautiful placethe room was very clean and nicely decoratedthe room was beautiful clean and comfortablequiet spotless and full of thoughtful touchesHost:
steven and john are great hostssteven and john are excellent hostsvery nice hosts great for couplesbeautiful home run by outstanding hostssteven and john are such gracious hostsRead more reviewsLocation:
convenient location and cute happy dogsvery comfortable accommodation in a lovely locationthe location and home are wonderfulthe area is very nice and was a perfect location for where we needed to bea beautiful home a great location and wonderful hosts
7. Private room with basic furniture
On a budget but would still like to explore Chesapeake? No problem! The Green Wood room is a nice and quiet space for budget travellers, complete with a kitchen and a shared bath. There will be other guests crashing in for the night, so if you don’t mind sharing living room space and enjoy meeting new people, then this Airbnb is ideal for you! It is also located a close driving distance to a lot of good restaurants and activities. Check out the link below for more information about this listing and on how to book a reservation.
Elkton, Maryland, United States
15.01 km (9.4 mi) from Lums Pond State ParkTop guest reviews
Amenities & Room:
softest bed linens nice room great valuegreat place to stay upstairs and downstairs bathroom availablefelt very comfortable in my roomCleanliness:
place was clean and tidyclean private and affordable place to spend the nightthe room was clean and basic good value for the priceHost:
she was very nice and helpfulshe was quite responsive and ensured that my stay was a pleasant onegreat airbnb and personable hostchristine was a great host and made quick accommodations when i showed up with an additional guestchristine and brad were really friendly and welcomingRead more reviewsLocation:
peaceful location great if you're looking for somewhere quietgood stay for the money private and quieta good place to stay very quietstaying at christine's place was well-worth it and i would certainly stay there againnice quiet neighborhood would stay again
8. Two-bedroom house with mid-century modern decor
If you don’t mind a simple yet cosy accommodation on your trip to Chesapeake, then check out this simple two-bedroom unit in the country. A nice and quiet space, this home is suitable for two guests and has an indoor fireplace, two bathrooms as well as wireless Internet connection. The owners even have horses, how cool is that?! The location is also very convenient as it is only a few meters away from the gorgeous Elk Neck State Forest and Elk Neck State Park. So, whether you want to stroll around Chesapeake or ditch the outdoors, this home is perfect for you!
14.95 km (9.3 mi) from Lums Pond State Park
9. Comfortable, new studio
This snug loft on our list has just been newly built and is perfect for a romantic getaway or a long-term stay. Its interiors are adorned with new furniture giving it a quiet and relaxed atmosphere. Being located in the centre of Elkton doesn’t hurt either as there are lots of sights to visit nearby. A good walk away from the loft is the port-like area, where plenty of boat launches and ramps are nearby.
14.88 km (9.3 mi) from Lums Pond State Park
10. Private basement with bedroom and living room
We all enjoy a bit of privacy when we go on a vacation, and the next Airbnb on our list offers just that! This spacious basement space has a private bathroom, a mini-fridge, a microwave and can accommodate up to three guests with its king-size and twin beds. At the back of the home is a nice landscape anyone would appreciate waking up to. Located close to plenty of restaurants and the town centre, it is convenient to go out, grab some dinner or just explore the place. So, if you feel like this listing is more to your liking, then you may contact the host to book a reservation ASAP!
Elkton, Maryland, United States
9.74 km (6.1 mi) from Lums Pond State ParkTop guest reviews
Amenities & Room:
there is definitely enough room for two peoplethis was a great quiet cozy warm place where i could workthe bathroom was pleasant and updatedCleanliness:
the living space was clean and tidyit was clean and exactly what we neededsuch an amazing and clean place so perfectsusan's place was vozy clean and comfortableclean and very nice bed is firmHost:
susan was a great hostthe host was very helpful ahead of time and upon arrivalsusan was a lovely host and made me feel very much at home in her private basement spacesusan and her husband were wonderful hosts overall very accommodatingsusan was a great host very friendly and accommodatingRead more reviewsLocation:
very close to great hiking trailsvery close to the university of delaware which makes it a great location if you are visitingsusan’s place is a perfect location for a work tripsusan’s place is centrally located and perfectly halfway in between philadelphia and baltimorevery private which is great and a great location
Get cosy in Chesapeake!
Maximize your stay by picking one of our top Airbnb vacation rentals in Chesapeake City, Maryland, and enjoy shopping in Chesapeake City to make your trip even more memorable!
If you’re seeking more choices, you’ll find numerous Airbnb vacation rentals in Elkton that offer a fantastic holiday experience. Additionally, you can explore a variety of exciting things to do in Elkton to enhance your trip.
Frequently asked questions about Airbnb vacation rentals in Chesapeake City, Maryland
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