Nicknamed the diamond town of the diamond state, Middletown, Delaware is a charming, lesser-known vacation spot. Nearly equidistant from Baltimore and Philadelphia, this town, with its red brick shops lining the streets of downtown, will reconnect you with American history away from the hubbub of the city. If you plan to pass through in August, you can enjoy the Olde Tyme Peach Festival and savor the delicious bites perfected by local restaurants. While it may be small, Middletown has a whole lot of heart that would be a shame to pass up. Check out these quintessential Airbnb vacation rentals in Middletown, Delaware.
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 February 02, 2024.
1. Stay and relax rooms (from USD 50)
This economical accommodation includes a private bathroom, a second bedroom and a twin sofa bed so it can accommodate additional guests. It is easy to visit local attractions such as the Chesapeake Bay and the Elk Neck State Park of Turkey Point lighthouse from this centrally-located home. You can also grab a bite at one of the restaurants nearby in North East, Chesapeake City and Elkton. If you feel like staying closer to home, take advantage of the spacious outdoor pool during the summer, or relax in the shared living space.
2. Spacious basement with a private bedroom and bath (from USD 54)
A thoughtfully decorated and modern accommodation, this private room and bath is located in the suburbs and conveniently close to the art and culture of downtown Middletown. Amenities include TV, Wi-Fi and free parking. Despite being a basement, this host has refurbished it into a warm and spacious space, complete with modern bathroom fixtures and plenty of lighting. Guests speak highly of the host’s friendliness, communication skills and attention to detail.
Top guest reviews
Amenities & Room:
wifi easy to connect and vannie was super nice and accommodatingCleanliness:
very nice clean spacious placethe space is clean spacious and quietthe residence was very clean and and very spaciousplace was clean very spacious comfortable and quietthe rooms are well kept and very cleanHost:
host was very friendly and kindvannie was an amazing hostgreat place great hostvannie was an amazing hostvannie is an awesome host with great accommodationsRead more reviewsLocation:
ideal location great value cozy space welcoming hosts
3. The Anchorage (from USD 1371)
Perfect for large groups, this stunning manor has 10 bedrooms - each with a private bathroom and access to the pool and patio - and can comfortably accommodate up to 16 guests. The Anchorage is located between Georgetown, Chesapeake City and Middletown. The scenic views of the surrounding farmland make for beautiful sunsets and tranquility. This rental also includes a full kitchen and common spaces to accommodate large groups.
Top guest reviews
Amenities & Room:
the furnishings and fixtures are luxurious and comfortablethe inn is beautiful very spacious with room for 15 people from age 8 - 77at night we used the firepit by the pool and were wowed by the starsthe family played card games into the night in the historical dining roomthe kitchen was smaller than we expected though not a problem for us in any wayCleanliness:
very clean and very spacious - especially the bedroomsit is beautifully decorated very clean and extremely spaciousthe check-in was super easy and the bedrooms were clean and interestingHost:
hannah is a wonderful host and very responsive to my many questionshannah was a fantastic host and very responsivethere is also a large lovely kind of sun room for dining togetherhannah was very helpful and responsive through the entire process - reservations pre-planning questions check-in and check outRead more reviewsLocation:
i highly recommend people consider this locationwonderful place great location and amenities for a corporate retreatwe would definitely recommend this place
4. Private room and bath for 3 (from USD 110)
The rustic touches at this ranch bed and breakfast remind you to enjoy the simpler things in life. Relish the fresh air of the surrounding farmlands, and feel at home knowing you can rest easy in the hospitality of your hosts, Bill and Cheryl. Additional sleeping arrangements can accommodate two more guests, who will also have their own private bathroom. Amenities such as heating, AC, TV, a washer and dryer, parking and Wi-Fi, are provided.
Top guest reviews
Cleanliness:
our room was very comfortable quiet and cleanit's incredibly peaceful clean and the pictures really don't do it justiceHost:
bill and cheryl were fantastic hosts and i felt thoroughly at home therevery kind and friendly hostsit's one of the friendliest most relaxing most welcoming places i've ever stayedRead more reviewsLocation:
although the location was remote the hospitality and comfort more than made up for the distance from town
5. The people's house (from USD 50)
Another budget-friendly Airbnb accommodation, this no-frills private room is located five minutes from the US 40 highway. It is also near several restaurants and Christiana Mall. The host, Vivian, is well-informed about the area and happy to provide recommendations. This is a great option if you are looking for somewhere to lay your head down for a night.
Top guest reviews
Amenities & Room:
lovely place comfortable room thoughtful amenitiesgreat place to stay for a nights sleep and hot showercomfortable bed spotless bath - definitely an excellent place for a good night’s sleepCleanliness:
clean and quietvery clean and cozycozy and very clean placevery clean organized and classyclean and cozy room in a quiet neighborhoodHost:
vivian was an awesome hostshe’s a wonderful hostsuper host and nice and respectvivian is such a gracious hostthe host is friendly pleasant and a great communicatedRead more reviewsLocation:
great location close to restaurants and storesthe location was great for my trip to chesapeake citygreat place to stay and only 20 minutes away from near by towns new castle etcit’s a perfect place to relax after workif you stay here you will love the pretty quiet family neighborhood with flowering trees
6. Lovely Victorian home in rural Townsend (from USD 150)
This traditional 1910 Victorian home is full of charm and warmth. Walk inside and you’ll pick up the scent of white sage, which the hosts burn in their home before every guest arrives to fill the home with positive energy. The private room has lots of natural light and access to a private bathroom. Enjoy the gorgeous scenery surrounding this rural abode on your way to explore the capitol, Dover, or nearby beaches in Rehoboth. If you’re in the area for the Firefly Musical Festival or NASCAR, know that this little town is only an hour and fifteen minutes to the Philadelphia airport, or one and a half hours to the Baltimore airport. Do note that the hosts have two cats so additional pets cannot be accommodated. As a bonus, your host Michele offers Reiki sessions on essential oils if that’s up your alley!
Top guest reviews
Amenities & Room:
the sunroom was beautiful and the hot tub was right there in the roomHost:
michelle and sean were the greatest hosts we could havedefinitely must be ok with very friendly catsRead more reviewsLocation:
michele and sean were more than accommodating and the location was great for firefly
7. Cheery private room
A quick 10 miles (16 km) from the University of Delaware, this private bedroom and bath boast a private entrance and parking availability. A microwave, refrigerator and toaster oven are available in the mini kitchen and living area adjacent to the bedroom. This is a comfortable, clean and quiet option for those needing easy access to interstate highways and nearby facilities.
Middletown, Delaware, United States
7.32 km (4.6 mi) from FrightlandSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
very comfortable quiet super clean room with kitchenette and private baththe bed was beyond amazing and we slept so wellCleanliness:
very nice clean place and great value in a quiet neighborhoodeasy access to the space clean and comfortableher home is beautiful and the space was spacious clean comfortable private and peacefulHost:
cynthia is a wonderful and gracious hostcynthia was great as far as being responsive with communicationscynthia and her husband are warm responsive helpful and just really good peopleRead more reviewsLocation:
super convenient and close to chesapeake citythis was the perfect place and location to stay before/after a century ridemy friend and i wanted a place to stay that was close to chesapeake city
8. Room #2 in a beautiful home
With a central location, this modern bedroom is close to local restaurants and shops. High ceilings let in copious amounts of natural light, providing for a comfortable stay. Whether you are traveling for business or pleasure, amenities such as heating, AC, Wi-Fi, ironing board and a laptop workspace will cover all your needs.
4.8 km (3.0 mi) from Frightland
9. Elegant and high-tech master bedroom
This private master bedroom is the picture of elegance. You can rest easy knowing you’ll have access to amenities such as a shared kitchen, Wi-Fi, a laptop workstation and a washer and dryer. This high-tech suite includes a flat-screen TV and your own private bathroom. Self check-in is a breeze with the building’s doorman, and your host is responsive to guests’ needs.
Middletown, Delaware, United States
9.5 km (5.9 mi) from Frightland
10. Chiefess 1
If you’re looking for a wallet-friendly accommodation but don’t want to lower your standards, this is the place for you. A simple bedroom with a private bathroom, this Airbnb is clean, spacious and located equidistant from Delaware and New Jersey beaches. The shared kitchen is fully stocked to meet your needs, and toiletry essentials are provided. Your host, Jessie, is quick to respond and happy to take your travel plans into consideration.
Bear, Delaware, United States
4.9 km (3.1 mi) from FrightlandTop guest reviews
Amenities & Room:
there was a private bathroom within the bedroom where i could put my belongings without disturbing anyone elsejessie was great only downfall was the room only had one small light which wasn’t very brightthe hotel-sized refrigerator in the room was perfectthe room also had a mini fridge and microwave i would definitely stay here againnice room one of 3 which would be good for a family or groupCleanliness:
great stay quiet clean and convenientcomfortable clean and a nice areavery clean welcoming atmosphere in a quiet upscale neighborhoodclean room quiet house nice neighborhoodeverything ample parking clean roomHost:
she is very brilliant and a great host together with her husband very welcoming and warmjessie made me feel very welcome in her home and the rest of her family was kind and politejessie was helpful and easy goingjessie and her husband were very pleasant and accommodatingRead more reviewsLocation:
the location of jessie's house is in a beautiful quite neighborhoodthe location is central and really peaceful we couldn’t be happier we chose to stay theregreat location jessie and family were good hosts
A breath of fresh air in Middletown
These options represent the best of small-town hospitality. Conveniently located along your travel route, or perhaps a bit off the beaten path, each is reflective of the heart its host put into ensuring you enjoyed your stay. If you’re tired of the humdrum of the nine to five routine, Middletown offers a refreshing respite. Next time you are craving the fresh air of the rolling countryside, check out one of these reliable Airbnb accommodations.
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