Apartment vacation rentals in Middletown

Find and book unique apartments on Airbnb

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Popular amenities for Middletown apartment rentals

Weekly apartment rentals

Guest favorite
A spacious living room features a comfortable couch adorned with colorful pillows. A potted plant adds a touch of greenery beside a contemporary armchair. Light filters through sheer curtains, and a soft area rug covers the hardwood floor, creating a cozy atmosphere.
Apartment in Downtown Hartford
4.91 out of 5 average rating, 46 reviews

Mod-Chic 1 Bedroom with Free Parking & Wifi

TimRating, 5 stars1 month ago
My first personal experience staying at an Airbnb was wonderful. However, the pictures did not accurately reflect what I found when I entered. The personal touches throughout the apartment made my stay very enjoyable and exciting. Thank you Oomi.
Guest favorite
A bright and inviting living space features a spacious sofa with soft cushions, complemented by a wooden coffee table. Natural light fills the room through large windows, while a modern television is mounted on the wall above a stylish cabinet. A dining area is also visible.
Apartment in Downtown New Haven
4.95 out of 5 average rating, 111 reviews

DTWN | Yale | Wooster Square | Laundry | Parking

LisaRating, 5 stars3 days ago
Fantastic stay! The hosts were super responsive and the place was perfectly clean. The location is fantastic for enjoying New Haven.
Guest favorite
A comfortable living space features a brown sofa with patterned cushions, a white coffee table, and a wall-mounted television. A small dining area with a wooden table and chairs is present. Light blue walls and a decorative mirror enhance the inviting atmosphere.
Apartment in Winsted
4.93 out of 5 average rating, 80 reviews

Getaway for a weekend! Close to Ski Sundown.

AnnetteRating, 5 stars1 week ago
My nephew found Alan and Karen's Airbnb for me for his wedding and it was perfect! The location was just up the hill from the venue and not apartment itself was perfect for me! It had everything I could have needed and it felt like home!
Guest favorite
A living area features a soft blue chair and a grand piano, complemented by a woven area rug on polished wooden floors. Natural light enters through large windows, illuminating the space and providing a view into adjoining rooms.
Apartment in New Haven
4.92 out of 5 average rating, 36 reviews

W1 Elegant, eclectic, spacious apartment

CandaceRating, 5 stars1 month ago
We had such a nice stay at Brian’s! The place was very large and comfortable. Brian was very responsive and helpful multiple times. The area was nice and we always felt safe. I would definitely recommend Brian and this location!
Superhost
The exterior of a three-story building is shown, featuring a white façade and a welcoming front porch with railings. Steps lead to the entrance, and the landscape includes a well-maintained lawn and signage indicating the building's purpose.
Apartment in West Haven
4.92 out of 5 average rating, 199 reviews

Perfection! 2 Bedroom Apt. Friends or Family!

TatianaRating, 5 stars2 weeks ago
Had a great stay, very clean and peaceful apartment, host was super responsive. Would definitely stay again!
Guest favorite
A comfortable living area features a dark leather sofa with decorative cushions, complementing a light wooden coffee table. Ethnic wall art and decorative masks add cultural interest. Natural light fills the space from the windows, while wooden accents provide warmth.
Apartment in Wallingford
5 out of 5 average rating, 22 reviews

Eclectic 2 BR, 1 Ba apt w/Free Off-Street Parking

GiovanniRating, 5 stars2 months ago
Stayed here for about a month and felt right at home with spacious rooms and lots of amenities provided, being 20 degrees in winter the apartment stood very warm and clean and it was a wonderful place to call home for 30 days. Kisha was very helpful and responsive when I needed to communicate and she’s very kind. If I’m ever near the area in the near future I would definitely book here again no hesitation! Thank you!
Guest favorite
A comfortable living space features a dark sofa and an inviting wooden coffee table. Behind it, a work desk with a chair is situated next to a bookcase filled with decorative items. A soft light illuminates the room, complemented by the warm tile floor.
Apartment in East Rock
4.9 out of 5 average rating, 112 reviews

Sperry House one bedroom private apartment

AbdoRating, 5 stars1 month ago
I had the pleasure of staying at Rosaria’s apartment for two months, and it was an amazing experience. The place was spotless, well-equipped, and had everything I needed for a comfortable stay. Rosaria herself was incredibly kind and helpful, always making sure everything was perfect. I highly recommend staying here to anyone looking for a great place. Thank you, Rosaria!
Superhost
The kitchen area features white cabinetry, a modern stove, and a refrigerator. A small dining table with two chairs is positioned on a patterned rug. Natural light enters through a window adorned with a blue curtain, enhancing the space's functionality.
Apartment in Norwich
4.9 out of 5 average rating, 110 reviews

Private Space with Full Kitchen

GabriellaRating, 5 stars3 weeks ago
Very nice. Definitely will book again! Huge bathroom

Private apartment rentals

Top guest favorite
A spacious living room is furnished with a comfortable sectional sofa, accented by patterned throw pillows. A round coffee table rests on a decorative area rug, and framed artwork adorns the walls. A table lamp provides soft lighting near a window with a sheer curtain.
Apartment in Canaan
4.99 out of 5 average rating, 137 reviews

West Main

DaleRating, 5 stars3 weeks ago
Exemplary accommodations! Everything about this place is well thought out and comfortable. (Every AirBnB host should do what Shirley did - label the light switches.) It's those intuitive touches that make this a great place to stay. We were close to family events in Norfolk, plus restaurants and amenities in Canaan. You really can't beat this experience. We were not able to make friends with the barn cat, but we tried!
Guest favorite
A spacious living area features a dark sectional sofa adorned with soft pillows and a cozy green throw. A small wooden tray is placed on the armrest. A modern kitchen and dining area are visible in the background, highlighting a neutral color palette.
Apartment in Andover
5 out of 5 average rating, 12 reviews

Beautiful 1 Bdr Oasis|10 miles to UCONN|473mbs|W/D

JimRating, 5 stars1 week ago
This was my second time staying here and was as lovely as the first. Look forward to the next visit!
Top guest favorite
A comfortable seating area features a pair of teal sofas adorned with decorative pillows. A marble-top coffee table sits centrally, complemented by a simple floral arrangement. Pale walls and patterned curtains enhance the space, while a green plant adds a touch of nature.
Apartment in Bristol
5 out of 5 average rating, 40 reviews

Two Bedroom Apartment on Forestville Bristol

IrinaRating, 5 stars1 month ago
We have previously stayed at another one of Eddy's properties, so we already had high expectations and they were all definitely met! Everything is exactly as described and lots of amenities available. We like how stocked the kitchen and bathroom is - it's super convenient and helpful to not have to think of those details. few mentions for future stays - we came on an unseasonably cold day and had to turn the heat up (all works perfectly) and benefitted from bringing our slippers/warm socks because the floor is a bit cold. Thoughtfully, there were rubber slides available for use! Also, getting in got a little confusing in the dark - our GPS told us we arrived when we were on the opposite side of the house. So just a heads up to anyone coming in, take a look at the map before driving in the dark :D
Top guest favorite
A compact kitchen area is shown, featuring white cabinetry and modern appliances. A round table with four black chairs, adorned with floral seat cushions, is set at the center. A small vase of fresh flowers adds a pop of color to the table.
Apartment in Torrington
4.98 out of 5 average rating, 161 reviews

Apartment on Main St.

GeneRating, 5 stars3 months ago
Molly's place was GREAT--a total gem for the area. The vibe and layout of the space was sunny, peaceful, and super welcoming. Easily one of my favorite AirBnB's ever--we will definitely be back! The kitchen had everything we needed and the whole apartment felt spacious and roomy, yet cozy. The backyard area is gorgeous! Even though the house is right on main street, the sound isolation was great and we slept well every night we were there (the most comfortable bed EVER also helped). We miss this place already!!
Superhost
A comfortable living area features a gray sofa with decorative cushions, positioned near a wall-mounted television. Natural light filters through sheer curtains on either side of the window. A patterned area rug adds warmth to the wooden floor.
Apartment in Bristol
5 out of 5 average rating, 4 reviews

Upstairs 2 bedroom apartment

JeremyRating, 5 stars3 months ago
I rented it for tenants to stay in during a repair at their apartment. My tenants chose to stay in their apartment instead so they never actually checked in. But Hameen was very flexible, even offering early check in since the contractors started early, and he refunded the cleaning fee since they never entered the apartment. The location is very central in Bristol and I can tell Hameen would be a great host for people that stay there.
Guest favorite
A cozy living area features a light-colored sofa adorned with patterned pillows. A wooden coffee table is placed in front, with a decorative book on top. The space transitions to a sleeping area, where a spacious bed is flanked by built-in shelves and framed artwork.
Apartment in New Haven
4.95 out of 5 average rating, 479 reviews

Urban Garden Suite

HilceaRating, 5 stars3 weeks ago
Beautiful, clean, and relaxing rental. Highly recommend staying here. Exactly what I needed after working my 12-hour shifts. I felt right at home!
Guest favorite
Apartment in New Haven
5 out of 5 average rating, 11 reviews

Elegant Apartment

Brianna Lyn NicoletteRating, 5 stars3 weeks ago
We loved it ! It’s beautiful ! The kids had a great time . It’s clean .. the bathrooms are beautiful both of them . It’s right off the highway and we had no complaints what’s so ever ! Would love to come back for sure ! Thanks for everything !! We tried to leave you a note but the pen was dead 😂 Thanks for having us !!
Guest favorite
A cozy living room showcases a red sofa adorned with decorative pillows featuring vintage phones. A low coffee table sits on a patterned rug, complemented by a small vase of fresh flowers. Natural light enters through a nearby window, enhancing the inviting ambiance.
Apartment in Downtown New Haven
4.86 out of 5 average rating, 95 reviews

Convenient, Private & Quiet apartment downtown

Catherine MargaretRating, 5 stars7 months ago
We really enjoyed our stay at Truman's house. We felt at home in the quiet, peaceful neighbourhood. We loved the eclectic pictures and little touches in the house. It was very comfortable and access to everything was easy to find. Truman was welcoming and always prompt to respond to our queries. Thank you for a very pleasant stay. David and Cathy Hersey

Apartment rentals with a hot tub

Superhost
A cozy living area features a leather sofa facing a vibrant area rug. A bookshelf holds various books, while a colorful pendant light hangs from the ceiling. Natural light filters through the space, highlighting furnishings and adding warmth to the room.
Apartment in Downtown New Haven
4.75 out of 5 average rating, 140 reviews

Luxury Penthouse Minutes to Yale

AmandaRating, 5 stars3 months ago
Great location. Easy check in and out.
A minimalistic studio apartment showcases a spacious bed with a dark coverlet. A small dining area with high chairs is positioned beside a large window. Exposed wooden beams and neutral-toned walls create a contemporary feel, while a decorative plant adds a touch of greenery.
Apartment in New Haven
4.29 out of 5 average rating, 14 reviews

Cellar Studio Apartment

ZoeRating, 5 stars6 months ago
Place was nice, exactly what was listed. Cozy space, cute red theme. Small but very clean bathroom. Air conditioner provided for room. I was happy with my stay! Door to get into the airbnb was annoying, it is a storm door, rather than a regular door with steps down. The ceiling is made only of wood above the bed, so you will hear EVERYTHING from upstairs, including footsteps, sitting on the bed, etc. and it sounds amplified. S.P’s initial message seemed very strict, but I asked questions and realized it is just a copy and paste message that she sends to everyone. Her instructions were very clear, could be warmer and more welcoming. WiFi was not provided until I asked. Over all, it really is a no-frills place and it gave me what I needed. Fees are high, though.
A spacious hot tub is subtly illuminated by flickering candles arranged on a surrounding wooden ledge. Steam rises gently from the water's surface, creating an inviting atmosphere. Greenery is placed around the area, enhancing the tranquil setting.
Apartment in Colebrook
5 out of 5 average rating, 25 reviews

Rural retreat in Colebrook CT

CarrieRating, 5 stars26 months ago
Marge was an amazing host who went to effort to ensure we were comfortable and taken care of. For example, in advance of our arrival she asked what type of bread and juice we preferred and if we wanted milk or cream for our coffee. She providd fresh eggs and even sent a dozen to our daughter who lives down the street. The apartment was welcoming, clean and cozy. The kitchen and pantry were well-supplied to meet our needs. We will definitely stay at Marge's next time we visit our daughter.
A spacious seating area is presented with four upholstered chairs arranged around a central table. A cozy fireplace is visible, while plants add a touch of nature. Large windows allow natural light to illuminate the space, enhancing the inviting ambiance.
Apartment in Norwich
4.74 out of 5 average rating, 35 reviews

Cozy spa condo with pools near Mystic/Mohegan Sun

LandenRating, 5 stars2 months ago
I really enjoyed my stay at Sherri's place. Something about it felt more like "home" than a rental property which I appreciate. I was able to enjoy the hot tub and sauna. The hours aren't posted but it was open pretty much the entire time I was there and not crowded. I also felt like there were a lot of extras at Sherri's place for cooking. There were two coffee makers and lots of spices. It was very convenient and there was to do around the area.
An open studio space features a queen bed with floral bedding, a cozy seating area, and a stone fireplace. Large windows provide natural light and reveal views of the outdoors. A dining area and bar with seating are visible, enhancing the inviting ambiance.
Apartment in Montville
4.75 out of 5 average rating, 120 reviews

Cozy Studio: Indoor Hot Tub & Inground Pool Access

ShainaRating, 5 stars1 month ago
Everything was amazing! Property owner was friendly and welcoming! Hoping to plan another trip to this spot it was truly an amazing weekend! Thank you!!!
A spacious bedroom features a light-colored wooden bed and dresser. A round mirror hangs on the wall, reflecting natural light. Sliding glass doors open to a balcony, with a small table and chairs visible outside. Fresh linens and towels are neatly arranged on the bed.
Apartment in Norwich
5 out of 5 average rating, 3 reviews

Golf course Villa

JulieRating, 5 stars3 weeks ago
Loved my stay at Rosemaries villa. It was beautiful and peaceful. Will definitely return!

Quick stats about apartment rentals in Middletown

  • Total rentals

    30 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore