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

airbnb Middletown CT
| 4 min read

Once a busy sailing port and industrial centre, Middletown is very much a residential city today. Its location, just next to the Connecticut River, gives it a nice atmospheric vibe. The US National Trust for Historic Preservation agrees, having selected Middletown as one of the five “Most Romantic Main Streets” in the country. For those who love art, there are several venues which show the city’s appreciation of it, for all ages. The Buttonwood Tree on Main Street is an intimate space for performance art, while the St Oddfellows Playhouse gives children of all ages an introduction to the world of theatre.

Given that Middletown is surrounded by various small towns, its name is certainly very fitting. Each town provides varying experiences. Portland, for example, can be found just across the river. It has a strong Italian influence, with many small delis and bakeries lining its streets. For visitors looking to visit the smaller towns in Connecticut, Middletown is a good starting base to do so. If you’re looking to make Middletown your next destination, here are 10 Airbnb vacation rentals you need to see.

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. Wesleyan room and ensuite bath

Whether you’re visiting a child in university or just looking for a place to crash in Middletown, this nice private room offers a comfy queen bed to suit your needs. The bathroom is ensuite, so guests can be assured of privacy.

The apartment is just three blocks from Wesleyan University and has complimentary, off-street parking. Should the need arise, a third person can be accommodated at a nominal fee. Homemade, freshly-baked pastries and fresh fruit will be available for guests in their breakfast basket, every morning.

Stayed at this property?
Middletown, Connecticut, United States
3.18 km (2.0 mi) from Wadsworth Falls State Park
466 reviews   Superhost Wifi Available
PRIVATE ROOM IN HOME 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
really appreciated the en-suite bathroom coffee machine and iron/ironing board
the room was perfectly comfortable and private with nice touches (helpful notes coffee/tea light breakfast fare)
the room is definitely cat-free
was such a nice surprise to find a coffee maker breakfast water and snacks
the space is very comfortable
very clean house nice family
the space is clean private and comfortable
the room was spotless and the bed extremely comfortable
the room was sparkling clean
the room and bathroom were clean and the bed was comfortable
rachel is a wonderful host
rachel is a great host
the hosts were very welcoming and accomodating
very warm and welcoming host family
rachel was very kind and welcoming
the great location to visit university just a few minutes ’ walk distance
the location was great however
great place in a nice location
outstanding location to the wesleyancampus
the location was ideal for a nice walk around campus with access to plenty of restaurant options
Read more reviews

2. Beautiful, modern guesthouse (from USD 207)

At the back of a 3-acre (1.2-hectare) property is this modern guesthouse, professionally designed by Studio A.T.E. Its interiors boast sleek, wood-panelled walls and flooring and contemporary furniture. The living area gives guests a view of the surrounding lush garden and pond.

Stony Creek and Guilford, two historic towns in Connecticut, are close, whilst the nearby, gorgeous, oceanside Hammonasset State Park is the perfect place to reconnect with nature and unwind.

Stayed at this property?
Guilford, Connecticut, United States
29.45 km (18.3 mi) from Wadsworth Falls State Park
453 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the wifi worked very well
the property is gorgeous and the view from the living room is so relaxing
heated bathroom floor was a nice touch
we loved the heated floor (and towel rack ) in the bathroom - such a great touch
clean and stylish in a beautiful setting
very clean comfortable and easy communication with the hosts
this place is very clean and modern as well as comfortable
this place is beautifully kept impeccably clean and serenely quiet
the house looks modern very clean very cozy
they were great hosts
they were incredibly responsive and welcoming: really great hosts
great place and amazing hosts
our host gave us some good recommendations e
the host goes out of their way to make you feel comfortable
perfect location on connecticut coast
the place is very near guilford with good restaurants and cute shops
it’s close to many great restaurants and hiking trails
what a lovely lovely bnb the location is simply ideal
great place to relax and get away from the city
Read more reviews

3. Quaint, two-bedroom apartment (from USD 116)

Close to both Wesleyan University and Middletown’s Main Street, this newly refurbished home boasts a location that many guests will find convenient. Guests will have access to the entire lower-level apartment, which comes with its own dedicated parking spot.

Aside from front and back bedrooms, the apartment also has plenty of other amenities, such as laundry, a dishwasher, fully-equipped kitchen and work/study area. There is also a small backyard and front porch seating area, from where guests can enjoy the cool breeze.

Stayed at this property?
Middletown, Connecticut, United States
3.49 km (2.2 mi) from Wadsworth Falls State Park
697 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
very comfortable beds and living areas
basically a full two-bedroom apartment with a good size bathroom and full kitchen
spacious clean and comfortable apartment
you'll find mark's place sparkling clean and clutter free
clean cozy and well cared for
everything was neat and clean and the beds were comfortable
clean comfortable everything you need
mark was a very helpful host
mark is a wonderful host
the host mark was very accommodating with our checkout time which we really appreciated
mark was a fantastic host and his place was perfect
the host mark is very easy to work with - helpful but not intrusive
perfect location for wesleyan too
great location and very comfortable
just a wonderful place right next to wesleyan university
it's a fantastic location for wesleyan
easy short walk to main st
Read more reviews

4. Sunny, private apartment (from USD 83)

A cosy, one-bedroom apartment, this home can accommodate up to three guests. The queen bed is perfect for couples, whilst a third person will be able to comfortably sleep on the couch. If you’re driving, there are several places of interest close by. Wesleyan University, Middletown city centre and the beautiful and historical 19th-century Saint Clements Castle are just a short five to 10-minute drive away.

Stayed at this property?
Portland, Connecticut, United States
8.14 km (5.1 mi) from Wadsworth Falls State Park
460 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
lots of space air conditioned and great bed
the window a/c units worked very well
there was easy parking effective air conditioning and a plenty of space
comfortable and spacious one bedroom apartment style air bnb
the home was full of amenities such as toiletries hygiene products snacks breakfast food coffee and fresh fruit
very clean and quiet
very clean and bright
the beddings and towels are very clean and also smell very clean just like in 5-star hotels
an extremely clean and convenient place
the place is very clean and spacious
sara is a great host
great place and great host quick responses and offered any help we needed
great space and awesome host
sara is a great host definitely recommended
sara quickly responds all the questions and very helpful
perfect location for us with easy access to middletown and all of central ct; 20 minute drive to hartford
good location and easy to find
sara’s place is cute and modern
it is close to a grocery store and several great restaurants
nice location and good value for the space
Read more reviews

5. Historic, two-bedroom house - One block from Main Street (from USD 120)

Guests will have the entire first-floor apartment to themselves in this 1849 Greek Revival brick home. The apartment has hardwood flooring, with exposed bricked walls, reflecting an Italian influence in its design.

The master bedroom has a king bed with decorative fireplace. The second bedroom has a queen bed. There is a large kitchen for any DIY meals and the backyard is also accessible to guests, where they can take a swing on the tire swing, to ponder the day’s events.

Stayed at this property?
Middletown, Connecticut, United States
3.62 km (2.3 mi) from Wadsworth Falls State Park
264 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
also much appreciated were the breakfast items provided - great coffee & english muffins
the historic greek revival was well stocked and comfortable
gorgeous jewel tones high ceilings beautiful furnishings comfortable space quiet and amazing kitchen for cooking
beautiful kitchen fully stocked with cookware fantastic mid-century modern furniture cozy beds quiet and safe area
bill & megan's place is a lovely and spacious ground floor apartment thoughtfully decorated with antiques and comfortable furniture
the place was very clean and an awesome old house
super clean and well taken care of place
awesome place clean tidy and fashionable
it is very spacious and clean
the apartment is very well equipped and clean
these guys certainly know how to host
the host was very accommodating and friendly
bill and meg were very good host
bill and megan are great hosts
bill and megan were excellent hosts
great location equidistant from weslyan and downtown
great location near the wesleyan campus
perfect location for a family visit to wesleyan
the location is great too as you can easily walk to main street
the house is a great location walking distance to both wesleyan university and middletown's main street
Read more reviews

6. Downtown apartment, near Wesleyan (from USD 96)

If you prefer being in the middle of all the action, this apartment will be perfect for you. Main Street, where there are plenty of shopping and dining options, is a short walking distance away. With three bedrooms, the house can host up to six guests. This may sound squeezy, but at about 1,000 square feet (93 square meters) of space, there’s plenty of space at home.

Stayed at this property?
Middletown, Connecticut, United States
3.65 km (2.3 mi) from Wadsworth Falls State Park
236 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
very comfortable beds and furniture
there was plenty of room for our family of four to spread out and feel comfortable
very good accommodations for two couples in the apartment
the home was very clean the furnishings were comfortable and the location was great
the place is great with three bedrooms and a big living room and newly modeled kitchen
the place was clean and spacious
it is clean and roomy
plenty of fresh towels and totally clean accommodations
clean and exactly what we needed
the house is clean and comfortable
monica was a gracious host
monica was a wonderful host
monica was a great host
hosts helpful and accommodating
she was very responsive and a great host
great location and walking distance to downtown and wesleyan
location was perfect to heart of town
so the location was great
the location is fantastic an easy walk to both the main street and the university
great location for a visit to middletown and wesleyan
Read more reviews

7. Private room in a bed and breakfast in Middletown (from USD 85)

Travelling alone? You may wish to consider this lovely single bedroom. It has a large queen bed and its own 27-inch TV, with full cable channels. WiFi is also a modern-day must that is available. The apartment has been newly furnished, so everything here is new. There is a kitchen that guests can use, but no extensive cooking is allowed.

Stayed at this property?
Middletown, Connecticut, United States
3.23 km (2.1 mi) from Wadsworth Falls State Park
87 reviews   Wifi Available
Private room in bed and breakfast 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
it would be helpful to have a small welcome card that lists the wifi access
wifi and tv made the stay just like home
super comfortable firm mattress
the actual room is quite cozy with a huge bed and a tv
i stayed again in the back bedroom where i slept soundly on a very comfortable bed
very clean and comfortable
room is clean tidy
the place is very clean
the room is very clean and nicely set up
the room was very comfortable and spotlessly clean
sonia was a very nice host
sonia was a lovely host
sonia was a warm welcoming host
sonia is a great host
sonia is a great host
comfortable home walking distance from wesleyan university
best for those looking for central location
she is also walking distance (about 15 min) to downtown where there are cute restaurants and shops
excellent stay at a wonderful location
terrific location if you're going to visit wesleyan or main st
Read more reviews

8. Private room in Clover Nook (from USD 85)

This is one of two Clover Nook rooms that the owners are letting on Airbnb. The room has a king bed that can comfortably sleep two guests. The bathroom, though, is shared with other Airbnb guests from a separate room. The owners will provide morning beverages, like coffee and tea, every day.

The room is located next to a ravine and creek, so there’s plenty around for nature lovers. Wesleyan University and the city centre are within walking distance.

Stayed at this property?
Middletown, Connecticut, United States
3.38 km (2.1 mi) from Wadsworth Falls State Park
53 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 1 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
we enjoyed our stay on the hottest night of the year and were grateful to have air conditioning
the room (with beautiful light and comfortable huge bed) made for a relaxing stay in middletown
what a beautiful room all the amenities discussed on the site are available
the room was huge and beautiful and extremely comfortable despite it being 100 degrees outside
cozy and charming spot with a huge backyard/garden that kathleen was willing to let me explore
the room was clean and the bed was very comfortable
the room and bathroom were quaint clean and well-maintained
lovely stay at kathleen's - the space is very clean cozy and sweet
beautiful sunrises comfortable bed spotless bathroom
the room was clean and comfortable full of sunlight
kathleen was a fun host who was sweet and knowledgeable about the area
kathleen is a gracious kind and accommodating host
kathleen was a gracious host lovely to talk to and very helpful
kathleen was very friendly making sure i had what i needed
kathleen was friendly and shared recommendations for what to do and where to eat in the area
great location for visiting wesleyan
great location for a visit to wesleyan
simple easy and close to wesleyan
5 mile walk from main street attractions
lovely room in a very convenient location in middletown would happily return
Read more reviews

9. Two-bedroom apartment near Wesleyan Campus

This is a quiet, second-storey apartment in a lovely Victorian home. The house is just a block away from Wesleyan University and the city centre is also just a short walk away. There’s plenty of space here, with a fully-equipped kitchen and large living area. The apartment’s highlights are its novelty spiral staircase and large spacious attic, with a crescent window to look down at the rest of the world below.

Stayed at this property?
Middletown, Connecticut, United States
3.26 km (2.1 mi) from Wadsworth Falls State Park
131 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
outlets throughout fully outfitted kitchen and wifi easily accessible
the apartment has been exquisitely restored to its original 1850 era look
the apartment was nicer than the photos
the beds were so comfortable and there were plenty of extra blankets and pillows
plus ample easy chairs and chaises throughout the rooms
clean comfortable and well laid out
very charming very clean and very comfortable
everything was very clean and the kitchen is very nice
really amazing beautiful and clean house
the apartment was very clean and the beds were very comfortable
host was very responsive
shannon was a wonderful host
shannon is a wonderful host
shannon is a wonderful host
shannon is a great host and very generous
great location for wesleyan campus
the location is perfect
the location is fabulous walking distance to wesleyan university and to downtown middletown
its location is great with easy walking distance into town or to weslyan campus
very close to wesleyan with serene neighborhood
Read more reviews

10. The Painted Lady House

Just half a mile (0.8 km) from downtown Middletown is this beautiful traditional home, steeped in history. It was built in 1887 by Charles Javis, the son of the treasurer of Brownstone Quarry and it was his wedding gift to his bride Louisa.

There is a lovely, well-maintained garden like you only see in movies, where you may see chickens and the owner’s children roaming around, in the day. Your private room gets you a queen bed with a view of the garden below. The owners also have two cats.

Stayed at this property?
Portland, Connecticut, United States
6.79 km (4.3 mi) from Wadsworth Falls State Park
107 reviews   Wifi Available
PRIVATE ROOM IN HOME 2 Beds 3 Guests 1 Bedroom 1 Bathrooms

Accommodates: 3

Top guest reviews
Amenities & Room:
so fun to eat breakfast with her chickens' fresh eggs too
it sneaked into my room twice that night because the door couldn’t be securely closed
one of the two cats in the house was really interested in my bed room
the room was clean and comfortable
however the cleanliness of the bathtub and bath rug need to be better
the room was clean and the bed was cozy
our room had ac towels toiletries clean linens and a tv
her home is comfortable clean and inviting
coreyanne was the perfect host
great hosts loved it
this host was nice and communicated well
coreyanne was lovely quick to respond and helpful
she is nice friendly and willing to help
cute historic home in great location
coreyanne's place is ideally located near many restaurants and shops and just accross the bridge from middletown
very close to wesleyan university; the family is friendly and the kids are quiet social and helpful
location was easy to find and she accommodated our late arrival well
the location is wonderful - about halfway between new haven and hartford
Read more reviews

Quality homes

Airbnb has many quality vacation rentals to fit every budget and it is no different here in Middletown. From full apartments to room rentals, visitors to the city will certainly have no shortage of options here.

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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