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Top 10 Airbnb Vacation Rentals In Middletown, Delaware - Updated 2020

Top 10 Airbnb Vacation Rentals In Middletown, Delaware - Updated 2020
Katherine
Katherine
Updated

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.

1. 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.

Spacious bsmt w a private bdrm and bath (shower)
Townsend, Delaware, United States
54 reviews
Private room in house 4 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The basement was very comfortable for our group of four
The bed was comfortable and that is perhaps the most important thing
spacious and quiet One of the queen beds is behind a privacy curtain so it does not have its own room
An amazing space for the price
Bathroom was stocked with everything we needed and the beds were comfy
Cleanliness:
The rooms are well kept and very clean
The residence was very clean and and very spacious
Place was clean very spacious
His house is very beautiful and clean and we really enjoyed our stay
Host:
Vannie was super friendly and an all around great host
Vannie was awesome and friendly and helpful
He is a very good host
He was very accommodating to our crazy schedule and made us feel at home
Vannie is quick to respond and a great host
Location:
Located in a safe neighborhood
There is a musty smell from the dampness
Ours was a late arrival followed by a pre-dawn departure we needed a place to get a good night's sleep
reasonable price and ease to carry out the transaction - from reservation to departure Thank you again
Vannie's place was a great stop
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2. The Anchorage (from USD 650)

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.

The Anchorage
Earleville, Maryland, United States
30 reviews
Entire house 10 Beds 10 Bedrooms 8 Bathrooms
Top guest reviews
Amenities & Room:
great kitchen and eating space
The kitchen also has a commercial sized refrigerator and a separate commercial sized freezer
you expect to have multiple cooks in the kitchen
The kitchen is on the tighter side if you're planning on cooking with more than 3 people at a time
All the bedrooms are large and very comfortable All in all a 5 star experience
Cleanliness:
Very beautiful house with large pool
The check-in was super easy and the bedrooms were clean and interesting Very unique
Having a bath for every bedroom was the best
It is beautifully decorated very clean and extremely spacious Truly a really fun experience
The bedrooms are large with 4 out of the 7 bedrooms having en-suite bathrooms
Host:
This property is great especially for family reunions or other gatherings with many people
Hannah is a wonderful host and very responsive to my many questions
Hannah was a fantastic host and very responsive
Hannah was very helpful and responsive through the entire process - reservations pre-planning questions check-in and check out We will definitely be coming back
and we couldn't think more highly of our hosts who went out of their way to show us around the property
Location:
What a great place Lots of space and loved the views Very quick response time too
I just mention it in case
e several families and a number of other adults)
The Anchorage is a great place to gather with friends and visit Eastern Shore Maryland Hannah
Perfect is the right way to describe our time here
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3. 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.

Private Room & Private Bath for 3
Townsend, Delaware, United States
11 reviews
Private room in house 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The room itself was just like the picture online
The view from our bedroom window was a farm field frequented by deer in the evening
The bed is extremely comfortable and to top it all off
Our room was very comfortable
and like the other guest rooms is set off from the rest of the home
Cleanliness:
The house and room were clean and spacious
Host:
and they made us breakfast in the morning
Very kind and friendly hosts
Cheryl met us in the driveway as we arrived and invited us in
Although the location was remote the hospitality and comfort more than made up for the distance from town
I cant say enough about this gorgeous country home and most of all the beautiful people that share it as an Airbnb
Location:
maps to get to the house
This was a great place - a supremely comfortable and homely farmhouse in a very peaceful rural setting but close enough to sights and amenities
Bill and Cheryl made my daughter and
Bill and Cheryl were wonderful
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4. Chiefess 1 (from USD 50)

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.

Chiefess 1
Bear, Delaware, United States
24 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The room was very spacious and comfortable although the air conditioner had a hard time keeping up with the very hot weather
It was very nice to have a mini fridge in the bedroom
The room I was in was a bit dark but bearable Bathroom was fairly standard
The hotel-sized refrigerator in the room was perfect
The WiFi was spontaneously fast
Cleanliness:
quiet clean and convenient
The house is clean and organized quite neighborhood
This location has two separate rooms each with a private bath
Host:
very accommodating and in all interactions
Upon arrival she warmly welcomed us with an open smile later on
She was caring and very welcoming
She is a wonderfull Person
Jessie made me feel very welcome in her home and the rest of her family was kind and polite
Location:
The location of Jessie's house is in a beautiful quite neighborhood
Really quite neighborhood and very easy to get around
Good neighborhood away from hustle and bustle House could be noisy at times as the voices carry
A beautiful home in a very nice neighborhood
I loved every minute of my stay at Jessie's home
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5. Lovely Victorian home in rural Townsend (from USD 100)

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!

Lovely Victorian in Rural Townsend - Sunroom
Townsend, Delaware, United States
6 reviews
Private room in house 1 Bed 1 Bedroom 2 Bathrooms
Top guest reviews
Amenities & Room:
The sunroom was beautiful and the hot tub was right there in the room
The bed was amazingly comfy-- would never guess it was an air mattress
This space is so much larger than it looks in the photos
The glass enclosed patio offers an evening under the stars
it really felt like a home away from home
Cleanliness:
The room was spacious and beautifully decorated
It was definitively a pleasure to be their guests
Host:
They were helpful providing us some food for the late mornings and they helped us to find convenient transportation
Super cool falling asleep and waking up with the glass ceiling
Michelle made us feel completely at home
She gave us very good recommendations on places to eat and visit
Michelle and Sean were the greatest hosts we could have We were visiting Dover for the Firefly festival and they made our experience so easy
Location:
My husband was leery of going to "just a random persons house"
We stayed here for our first time going to Firefly Music Festival and it was a great location from the venue and made us feel right at home
The neighborhood was very safe and the accommodations were better than the pictures showed
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6. The people's house (from USD 35)

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.

The people's house.
Bear, Delaware, United States
105 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
Private room with tv and bathroom
Very nice private room in house
The place was easy to find
Lovely place comfortable room
Bathroom was adjacent to room and will be all your own
Cleanliness:
The house was sparkling clean and everything was placed with thought and perfection
Vivian's place was so clean and comfy
Vivian's accommodations are very clean
My room and bathroom were very clean and her and her husband were very welcoming
It was a good place to rest after a long day working
Host:
and she was extremely accommodating
Super host and nice and respect
She's very welcoming and can hold a great conversation
Homey with informative good conversation
(she showed me some of her beautiful quilt work )
Location:
and I did not bother looking anywhere else
Her home in Bear is in a great location easily accessible to anywhere
For travelers it is easy to get to and if you need something or want to go out and eat options are nearby
everything provided easy to get to Great location
The location was great for my trip to Chesapeake City Vivian is pleasant and responsive
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7. Cheery private room (from USD 60)

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.

Cheery private room
Middletown, Delaware, United States
16 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
dining area bathroom with all amenities
Easy access to the space
yet I had plenty of quiet and undisturbed time
comfortable private and peaceful
Her home is beautiful and the space was spacious
Host:
she responded quickly to my questions
Cynthia was easy to work with humoring my requests with charm
Cynthia is a wonderful and gracious host
Cynthia was a great host
The location was great for me easy access to both DE-1 and 301 to I-95 as I needed to head both north and south during my stay Cynthia made sure I had what I needed
Location:
The neighborhood is lovely and very quiet too
Great location great space and clean
This was the perfect place and location to stay before/after a century ride
; I did not want to get up the next morning Peaceful area with great scenery Quite beautiful
Space was exactly as advertised Super convenient and close to Chesapeake City
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8. Stay and relax rooms

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.

Stay and Relax rooms
78 reviews
Private room 2 Beds 4 Guests

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9. 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.

Room # 2 in a beautiful home
4 reviews
Private room 1 Bed 2 Guests

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10. 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.

Elegant and High-Tech Master's Bedroom (Queen Bed)
Middletown, Delaware, United States
6 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom

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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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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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