
Apartment vacation rentals in Middletown
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Middletown
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middletown apartment rentals
Weekly apartment rentals

Mod-Chic 1 Bedroom with Free Parking & Wifi
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.

DTWN | Yale | Wooster Square | Laundry | Parking
Fantastic stay! The hosts were super responsive and the place was perfectly clean. The location is fantastic for enjoying New Haven.

Getaway for a weekend! Close to Ski Sundown.
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!

W1 Elegant, eclectic, spacious apartment
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!

Perfection! 2 Bedroom Apt. Friends or Family!
Had a great stay, very clean and peaceful apartment, host was super responsive. Would definitely stay again!

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

Sperry House one bedroom private apartment
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!

Private Space with Full Kitchen
Very nice. Definitely will book again! Huge bathroom
Private apartment rentals

West Main
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!

Beautiful 1 Bdr Oasis|10 miles to UCONN|473mbs|W/D
This was my second time staying here and was as lovely as the first. Look forward to the next visit!

Two Bedroom Apartment on Forestville Bristol
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

Apartment on Main St.
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!!

Upstairs 2 bedroom apartment
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.

Urban Garden Suite
Beautiful, clean, and relaxing rental. Highly recommend staying here. Exactly what I needed after working my 12-hour shifts. I felt right at home!

Elegant Apartment
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 !!

Convenient, Private & Quiet apartment downtown
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

Luxury Penthouse Minutes to Yale
Great location. Easy check in and out.

Cellar Studio Apartment
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.

Rural retreat in Colebrook CT
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.

Cozy spa condo with pools near Mystic/Mohegan Sun
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.

Cozy Studio: Indoor Hot Tub & Inground Pool Access
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!!!

Golf course Villa
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
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- Hudson Valley Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Rentals with a washer and dryer Middletown
- Family-friendly rentals Middletown
- Condo rentals Middletown
- Pet-friendly rentals Middletown
- Rentals with a fireplace Middletown
- Rentals with a fire pit Middletown
- House rentals Middletown
- Rentals with a patio Middletown
- Cottage rentals Middletown
- Rentals with outdoor seating Middletown
- Apartment rentals Middlesex County
- Apartment rentals Connecticut
- Apartment rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Cooper's Beach, Southampton
- Clinton Town Beach
- Woodmont Beach
- Shennecossett Beach
- Six Flags New England
- Thunder Ridge Ski Area
- Shinnecock Hills Golf Club
- Seaside Beach
- Walnut Public Beach
- Shoreham Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Jennings Beach
- The Connecticut Golf Club
- Sasco Hill Beach
- Fairfield Public Beach
- Yale University Art Gallery
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes