
Apartment vacation rentals in Middletown
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Top-rated apartment rentals in Middletown
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Vacation rentals for every style
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Popular amenities for Middletown apartment rentals
Weekly apartment rentals

New, modern studio steps from downtown Chester CT
Great place! We stayed here on our wedding night and it exceeded our expectations. Quaint, well maintained and beautifully decorated. It was modern, clean with thoughtful attention to detail. Located near the center of Chester, a true hidden gem on the CT river. Friendly hosts.

Designer's Den in the Business District
Fantastic home! Our host was incredibly friendly and quick to respond. Location is very walkable with lots of things to do and places to eat. Had a few amenity issues but our host was quick to offer alternative options and additional services. Would love to be back :))

Cozy East Rock apartment
Immaculate space. Comfy couch and bed. Soft linens. Easy check in. Nice, historic neighborhood. Highly recommend!

Meadowview & Pondside Retreat
Becky's place was such a delight. As a person who loves nature, peace, meditation and is low key and down-to-earth, this was my match. The big windows and pond views were lovely. The bed is comfy, the layout intuitive. I felt at home from her communication, flexibility, to the casual yet chic furnishings. It's also in close proximity to a state park. She's very responsive and warm. Great experience from front to finish.

Mod-Chic 1 Bedroom with Free Parking & Wifi
I really enjoyed my stay. It was easy to access and very clean. I was very comfortable. Had everything I needed.

Seasons Hospitality Cozy 1BR Waiting for you C1
I was in town visiting family for just a couple of days, and this apartment was a great landing spot. The living room was cozy, the kitchen was well stocked (love having a blender!), and the location was so convenient for getting around CT being just of the Parkway, 68 and a quick drive to 91 off Tulles. Karl was super helpful and responsive. Internet was also great for working during the day. Would definitely recommend a stay here.

Two Bedroom Apartment on Forestville Bristol
We were so happy to find this lovely hidden gem in our family’s neighborhood. It is so much better than the local hotels we’ve had to endure thru the years when we come to visit. The owner has done an amazing job with his properties and we appreciate how comfortable we felt. We used one room with the 2 twin beds as our “dressing room” which was closest to the bathroom. Well equipped kitchen and laundry room. Primary bedroom has a Queen bed and nice lounge chair. The neighbor is quiet and safe. We look forward to our next stay!

Cozy Private Lake Q Retreat
Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.
Private apartment rentals

Life on the Farm
We loved our stay here for when we visited New Haven! The place was clean and worked perfect for our dog! We loved the farm outside and the peaceful and private area outside. Would stay here again!

Everything you need! Apartment!
Jerry is an amazing host and has a great place to stay. You will find everything you need for a short or long stay with the full kitchen. The AirBnb is in a quiet part of Waterbury, right on the edge, and has a grocery store less than 10 minutes away by car on a low traffic side road. Highway 84 is less than 10 minutes in the other direction and lets you go explore the rest of Connecticut and return back after a long day with ease. This is our second time staying at this AirBnb and it was just as wonderful as the first time. Can't recommend this place enough for anyone looking to stay in the area!

Spacious 1 BR Steps From Yale
Beautiful home with very kind hosts. We had a very peaceful stay.

In-law Private Studio Apartment
We had a wonderful experience! We traveled to New Haven for a concert. It was only a 15 minute drive from the home. The Airbnb had everything we needed such as extra towels, snacks, and even a homemade candle, which smells lovely. Ryan was quick to respond and made sure we had everything. I would book with them again.

Apt near Big E, Six Flags, Bradley airport
Viktoriya’s place was a perfect place for a quick stay! Lots of windows to open for a breeze to come in to cool down the place! Viktoriya was very responsive and flexible. My flight landed at 1 and she let me check in early, free of charge! I’ll be back in Hartford this time next year and I would come back here!

Cozy Apartment with Water View of Brook
We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!

Enjoy a Farm Stay without the Work
This was a delightful stay, and I wish we hadn't had so many family obligations so we could have enjoyed the place better. I so wanted to take time to relax on the beautiful and inviting back patio and just explore the property. I love historic places. We will definitely stay again next time we have family events in the area. Carol reached out to us and made us feel very welcome. We knew we had help if we needed something, but we didn't experience any issues at all, so didn't need to reach out. Great host for sure!!!

Cozy 1b/1b beautiful views Hopeville Wtby 2nd Flr
Sonia was a fantastic host, she immediately took care of any questions you may have had. She responded to any text quickly. The place was completely clean and in a good area of town. Walking distance to local park. Not a long drive to get gas or go to a store for whatever you may have needed!! 👏😊
Apartment rentals with a hot tub

Luxury Penthouse Minutes to Yale
My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

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
The place was very clean and easy to access. It felt safe and had great amenities. The extra large bed was so nice and the neighbor hood was super cute!

Cozy Corner, by the Spa
Amazing stay! Relaxing and our host was very communicative

Sweet Dreams Retreat
Melissa and Geoff's place is in beautiful surroundings and well within a short drive to excellent restaurants, museums and outdoor activities. We were there during an especially rainy and cool period, but the apartment kept us toasty and warm after a day of dodging the raindrops. The king size bed was lovely and a white machine lulled us to sleep. The deck attached to the house was wonderful and when the weather looked as if the blue skies were here to stay, Melissa asked if we wanted dry cushions for the chairs- just a lovely thought. The gardens were just beginning to bloom and the property is spotless. We will definitely return to Sweet Dreams; the apartment was a pleasure to be in. Andrea and Ray

Cozy Studio: Indoor Hot Tub & Inground Pool Access
If you are looking for a peaceful stay with an absolutely gorgeous view I fully recommend this place! The sound of nature as you look down the mountain full of beautiful trees and landscape! The hot tub in the space was relaxing and perfect! Everything you need in your little area. Also, Al was an absolute pleasure. He was sweet, very accommodating, and gave great recommendations! I would highly recommend and I would love to return in the fall to see the view in color!

Villa in Norwich
The condo was lovely——extremely clean and well located for our wedding weekend at the inn. Lots of great product and extras available for everything you forget to bring!

Chalet Tré
The place was beautiful and Gabrielle was so sweet and answered all of our questions! Thank you for having us! We will be back! :)
Quick stats about apartment rentals in Middletown
Total rentals
30 properties
Nightly prices starting at
G$6,295 GYD 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
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- Beach
- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Amagansett Beach
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Sherwood Island State Park
- Long Island Aquarium
- Bayview Beach
- South Jamesport Beach
- Attawan Beach