Top 10 Airbnb Vacation Rentals In Middletown, Delaware - Updated 2024

airbnb Middletown DE
| 3 min read

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.

21.94 km (13.7 mi) from Frightland
78 reviews  
Private room 2 Beds 4 Guests

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.

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Townsend, Delaware, United States
13.27 km (8.3 mi) from Frightland
64 reviews   Wifi Available
PRIVATE ROOM IN HOME 4 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
wifi easy to connect and vannie was super nice and accommodating
very nice clean spacious place
the space is clean spacious and quiet
the residence was very clean and and very spacious
place was clean very spacious comfortable and quiet
the rooms are well kept and very clean
host was very friendly and kind
vannie was an amazing host
great place great host
vannie was an amazing host
vannie is an awesome host with great accommodations
ideal location great value cozy space welcoming hosts
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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.

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Earleville, Maryland, United States
21.77 km (13.6 mi) from Frightland
87 reviews   Wifi Available
ENTIRE HOME 10 Beds 16 Guests 10 Bedrooms 8 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the furnishings and fixtures are luxurious and comfortable
the inn is beautiful very spacious with room for 15 people from age 8 - 77
at night we used the firepit by the pool and were wowed by the stars
the family played card games into the night in the historical dining room
the kitchen was smaller than we expected though not a problem for us in any way
very clean and very spacious - especially the bedrooms
it is beautifully decorated very clean and extremely spacious
the check-in was super easy and the bedrooms were clean and interesting
hannah is a wonderful host and very responsive to my many questions
hannah was a fantastic host and very responsive
there is also a large lovely kind of sun room for dining together
hannah was very helpful and responsive through the entire process - reservations pre-planning questions check-in and check out
i highly recommend people consider this location
wonderful place great location and amenities for a corporate retreat
we would definitely recommend this place
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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.

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Townsend, Delaware, United States
20.6 km (12.8 mi) from Frightland
17 reviews   Wifi Available
PRIVATE ROOM IN HOME 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
our room was very comfortable quiet and clean
it's incredibly peaceful clean and the pictures really don't do it justice
bill and cheryl were fantastic hosts and i felt thoroughly at home there
very kind and friendly hosts
it's one of the friendliest most relaxing most welcoming places i've ever stayed
although the location was remote the hospitality and comfort more than made up for the distance from town
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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.

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Bear, Delaware, United States
9.21 km (5.8 mi) from Frightland
187 reviews   Superhost Wifi Available
PRIVATE ROOM IN HOME 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Amenities & Room:
lovely place comfortable room thoughtful amenities
great place to stay for a nights sleep and hot shower
comfortable bed spotless bath - definitely an excellent place for a good night’s sleep
clean and quiet
very clean and cozy
cozy and very clean place
very clean organized and classy
clean and cozy room in a quiet neighborhood
vivian was an awesome host
she’s a wonderful host
super host and nice and respect
vivian is such a gracious host
the host is friendly pleasant and a great communicated
great location close to restaurants and stores
the location was great for my trip to chesapeake city
great place to stay and only 20 minutes away from near by towns new castle etc
it’s a perfect place to relax after work
if you stay here you will love the pretty quiet family neighborhood with flowering trees
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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!

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Townsend, Delaware, United States
15.53 km (9.7 mi) from Frightland
7 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 2 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
the sunroom was beautiful and the hot tub was right there in the room
michelle and sean were the greatest hosts we could have
definitely must be ok with very friendly cats
michele and sean were more than accommodating and the location was great for firefly
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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.

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Middletown, Delaware, United States
7.32 km (4.6 mi) from Frightland
28 reviews   Superhost Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
very comfortable quiet super clean room with kitchenette and private bath
the bed was beyond amazing and we slept so well
very nice clean place and great value in a quiet neighborhood
easy access to the space clean and comfortable
her home is beautiful and the space was spacious clean comfortable private and peaceful
cynthia is a wonderful and gracious host
cynthia was great as far as being responsive with communications
cynthia and her husband are warm responsive helpful and just really good people
super convenient and close to chesapeake city
this was the perfect place and location to stay before/after a century ride
my friend and i wanted a place to stay that was close to chesapeake city
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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.

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4.8 km (3.0 mi) from Frightland
4 reviews  
Private room 1 Bed 2 Guests

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.

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Middletown, Delaware, United States
9.5 km (5.9 mi) from Frightland
6 reviews  
Private room in house 1 Bed 1 Bedroom 1 Bathroom

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.

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Bear, Delaware, United States
4.9 km (3.1 mi) from Frightland
24 reviews  
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
there was a private bathroom within the bedroom where i could put my belongings without disturbing anyone else
jessie was great only downfall was the room only had one small light which wasn’t very bright
the hotel-sized refrigerator in the room was perfect
the room also had a mini fridge and microwave i would definitely stay here again
nice room one of 3 which would be good for a family or group
great stay quiet clean and convenient
comfortable clean and a nice area
very clean welcoming atmosphere in a quiet upscale neighborhood
clean room quiet house nice neighborhood
everything ample parking clean room
she is very brilliant and a great host together with her husband very welcoming and warm
jessie made me feel very welcome in her home and the rest of her family was kind and polite
jessie was helpful and easy going
jessie and her husband were very pleasant and accommodating
the location of jessie's house is in a beautiful quite neighborhood
the location is central and really peaceful we couldn’t be happier we chose to stay there
great location jessie and family were good hosts
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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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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Katherine is a 24 year old graduate student from the United States. Her latest travels include Japan, Malaysia, Thailand and Uganda. Photography and writing are her ideal ways to explore and...Read more

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