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 May 16, 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.
Middletown, Connecticut, United States
3.18 km (2.0 mi) from Wadsworth Falls State ParkSuperhost
Accommodates: 3
Top guest reviews
Amenities & Room:
really appreciated the en-suite bathroom coffee machine and iron/ironing boardthe room was perfectly comfortable and private with nice touches (helpful notes coffee/tea light breakfast fare)the room is definitely cat-freewas such a nice surprise to find a coffee maker breakfast water and snacksthe space is very comfortableCleanliness:
very clean house nice familythe space is clean private and comfortablethe room was spotless and the bed extremely comfortablethe room was sparkling cleanthe room and bathroom were clean and the bed was comfortableHost:
rachel is a wonderful hostrachel is a great hostthe hosts were very welcoming and accomodatingvery warm and welcoming host familyrachel was very kind and welcomingRead more reviewsLocation:
the great location to visit university just a few minutes ’ walk distancethe location was great howevergreat place in a nice locationoutstanding location to the wesleyancampusthe location was ideal for a nice walk around campus with access to plenty of restaurant options
2. Beautiful, modern guesthouse (from USD 250)
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.
Top guest reviews
Amenities & Room:
the wifi worked very wellthe property is gorgeous and the view from the living room is so relaxingheated bathroom floor was a nice touchwe loved the heated floor (and towel rack ) in the bathroom - such a great touchCleanliness:
clean and stylish in a beautiful settingvery clean comfortable and easy communication with the hoststhis place is very clean and modern as well as comfortablethis place is beautifully kept impeccably clean and serenely quietthe house looks modern very clean very cozyHost:
they were great hoststhey were incredibly responsive and welcoming: really great hostsgreat place and amazing hostsour host gave us some good recommendations ethe host goes out of their way to make you feel comfortableRead more reviewsLocation:
perfect location on connecticut coastthe place is very near guilford with good restaurants and cute shopsit’s close to many great restaurants and hiking trailswhat a lovely lovely bnb the location is simply idealgreat place to relax and get away from the city
3. Quaint, two-bedroom apartment (from USD 120)
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.
Top guest reviews
Amenities & Room:
very comfortable beds and living areasbasically a full two-bedroom apartment with a good size bathroom and full kitchenCleanliness:
spacious clean and comfortable apartmentyou'll find mark's place sparkling clean and clutter freeclean cozy and well cared foreverything was neat and clean and the beds were comfortableclean comfortable everything you needHost:
mark was a very helpful hostmark is a wonderful hostthe host mark was very accommodating with our checkout time which we really appreciatedmark was a fantastic host and his place was perfectthe host mark is very easy to work with - helpful but not intrusiveRead more reviewsLocation:
perfect location for wesleyan toogreat location and very comfortablejust a wonderful place right next to wesleyan universityit's a fantastic location for wesleyaneasy short walk to main st
4. Sunny, private apartment (from USD 79)
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.
Top guest reviews
Amenities & Room:
lots of space air conditioned and great bedthe window a/c units worked very wellthere was easy parking effective air conditioning and a plenty of spacecomfortable and spacious one bedroom apartment style air bnbthe home was full of amenities such as toiletries hygiene products snacks breakfast food coffee and fresh fruitCleanliness:
very clean and quietvery clean and brightthe beddings and towels are very clean and also smell very clean just like in 5-star hotelsan extremely clean and convenient placethe place is very clean and spaciousHost:
sara is a great hostgreat place and great host quick responses and offered any help we neededgreat space and awesome hostsara is a great host definitely recommendedsara quickly responds all the questions and very helpfulRead more reviewsLocation:
perfect location for us with easy access to middletown and all of central ct; 20 minute drive to hartfordgood location and easy to findsara’s place is cute and modernit is close to a grocery store and several great restaurantsnice location and good value for the space
5. Historic, two-bedroom house - One block from Main Street (from USD 199)
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.
Top guest reviews
Amenities & Room:
also much appreciated were the breakfast items provided - great coffee & english muffinsthe historic greek revival was well stocked and comfortablegorgeous jewel tones high ceilings beautiful furnishings comfortable space quiet and amazing kitchen for cookingbeautiful kitchen fully stocked with cookware fantastic mid-century modern furniture cozy beds quiet and safe areabill & megan's place is a lovely and spacious ground floor apartment thoughtfully decorated with antiques and comfortable furnitureCleanliness:
the place was very clean and an awesome old housesuper clean and well taken care of placeawesome place clean tidy and fashionableit is very spacious and cleanthe apartment is very well equipped and cleanHost:
these guys certainly know how to hostthe host was very accommodating and friendlybill and meg were very good hostbill and megan are great hostsbill and megan were excellent hostsRead more reviewsLocation:
great location equidistant from weslyan and downtowngreat location near the wesleyan campusperfect location for a family visit to wesleyanthe location is great too as you can easily walk to main streetthe house is a great location walking distance to both wesleyan university and middletown's main street
6. Downtown apartment, near Wesleyan (from USD 94)
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.
Top guest reviews
Amenities & Room:
very comfortable beds and furniturethere was plenty of room for our family of four to spread out and feel comfortablevery good accommodations for two couples in the apartmentthe home was very clean the furnishings were comfortable and the location was greatthe place is great with three bedrooms and a big living room and newly modeled kitchenCleanliness:
the place was clean and spaciousit is clean and roomyplenty of fresh towels and totally clean accommodationsclean and exactly what we neededthe house is clean and comfortableHost:
monica was a gracious hostmonica was a wonderful hostmonica was a great hosthosts helpful and accommodatingshe was very responsive and a great hostRead more reviewsLocation:
great location and walking distance to downtown and wesleyanlocation was perfect to heart of townso the location was greatthe location is fantastic an easy walk to both the main street and the universitygreat location for a visit to middletown and wesleyan
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.
Top guest reviews
Amenities & Room:
it would be helpful to have a small welcome card that lists the wifi accesswifi and tv made the stay just like homesuper comfortable firm mattressthe actual room is quite cozy with a huge bed and a tvi stayed again in the back bedroom where i slept soundly on a very comfortable bedCleanliness:
very clean and comfortableroom is clean tidythe place is very cleanthe room is very clean and nicely set upthe room was very comfortable and spotlessly cleanHost:
sonia was a very nice hostsonia was a lovely hostsonia was a warm welcoming hostsonia is a great hostsonia is a great hostRead more reviewsLocation:
comfortable home walking distance from wesleyan universitybest for those looking for central locationshe is also walking distance (about 15 min) to downtown where there are cute restaurants and shopsexcellent stay at a wonderful locationterrific location if you're going to visit wesleyan or main st
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.
Top guest reviews
Amenities & Room:
we enjoyed our stay on the hottest night of the year and were grateful to have air conditioningthe room (with beautiful light and comfortable huge bed) made for a relaxing stay in middletownwhat a beautiful room all the amenities discussed on the site are availablethe room was huge and beautiful and extremely comfortable despite it being 100 degrees outsidecozy and charming spot with a huge backyard/garden that kathleen was willing to let me exploreCleanliness:
the room was clean and the bed was very comfortablethe room and bathroom were quaint clean and well-maintainedlovely stay at kathleen's - the space is very clean cozy and sweetbeautiful sunrises comfortable bed spotless bathroomthe room was clean and comfortable full of sunlightHost:
kathleen was a fun host who was sweet and knowledgeable about the areakathleen is a gracious kind and accommodating hostkathleen was a gracious host lovely to talk to and very helpfulkathleen was very friendly making sure i had what i neededkathleen was friendly and shared recommendations for what to do and where to eat in the areaRead more reviewsLocation:
great location for visiting wesleyangreat location for a visit to wesleyansimple easy and close to wesleyan5 mile walk from main street attractionslovely room in a very convenient location in middletown would happily return
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.
Middletown, Connecticut, United States
3.26 km (2.1 mi) from Wadsworth Falls State ParkAccommodates: 4
Top guest reviews
Amenities & Room:
outlets throughout fully outfitted kitchen and wifi easily accessiblethe apartment has been exquisitely restored to its original 1850 era lookthe apartment was nicer than the photosthe beds were so comfortable and there were plenty of extra blankets and pillowsplus ample easy chairs and chaises throughout the roomsCleanliness:
clean comfortable and well laid outvery charming very clean and very comfortableeverything was very clean and the kitchen is very nicereally amazing beautiful and clean housethe apartment was very clean and the beds were very comfortableHost:
host was very responsiveshannon was a wonderful hostshannon is a wonderful hostshannon is a wonderful hostshannon is a great host and very generousRead more reviewsLocation:
great location for wesleyan campusthe location is perfectthe location is fabulous walking distance to wesleyan university and to downtown middletownits location is great with easy walking distance into town or to weslyan campusvery close to wesleyan with serene neighborhood
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.
Portland, Connecticut, United States
6.79 km (4.3 mi) from Wadsworth Falls State ParkAccommodates: 3
Top guest reviews
Amenities & Room:
so fun to eat breakfast with her chickens' fresh eggs tooit sneaked into my room twice that night because the door couldn’t be securely closedone of the two cats in the house was really interested in my bed roomCleanliness:
the room was clean and comfortablehowever the cleanliness of the bathtub and bath rug need to be betterthe room was clean and the bed was cozyour room had ac towels toiletries clean linens and a tvher home is comfortable clean and invitingHost:
coreyanne was the perfect hostgreat hosts loved itthis host was nice and communicated wellcoreyanne was lovely quick to respond and helpfulshe is nice friendly and willing to helpRead more reviewsLocation:
cute historic home in great locationcoreyanne's place is ideally located near many restaurants and shops and just accross the bridge from middletownvery close to wesleyan university; the family is friendly and the kids are quiet social and helpfullocation was easy to find and she accommodated our late arrival wellthe location is wonderful - about halfway between new haven and hartford
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.
History
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