
Condo vacation rentals in Middletown
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Top-rated condo rentals in Middletown
Guests agree: these condos 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 condo rentals
Weekly condo rentals

Stunning, Spacious, Spotless. Close to Yale.
Camila was a great host, very responsive and always helpful. The apartment was clean, tidy and cosy and made us feel at home very quickly. Location was good, walkable distance to New Haven Green and its surroundings. All in all, we enjoyed our stay very much and would recommend Camila’s place to anyone planing to spend some time in New Haven.

Posh Pad in The Business District
Thanks for a great stay

The Anchor at Soundview · Beach+Ocean+Sunrise
We really enjoyed this spot! We walked to the beach as often as possible and we were able to walk to Teddy's Pizza from the location which was a huge plus with their amazing food! Hosts were very responsive and easy to communicate with!

Entire place to yourself Cromwell/Middletown Line
Elizabeth's place was extremely well appointed. Nice towels and sheets, and comfortable sofa/chairs. Kitchen is well equipped. Bathroom has a nice big tub, and her decorations are very nice. Definitely has a woman's touch!

New Britain "Joy of Small Space" Condo
Muna is an awesome host. She is super responsive and always gives us good advise. We had a long stay and the place is very warm, clean, and very comfortable. Excellent location with everything you need, we had a wonderful stay and family vacation at her place. Thank you once again Muna, we look forward to come back again!

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr
This was our second stay at Dariel’s place. It is perfect for our family and I always check to see if it is available when we are visiting the area. It is spacious yet cozy, and well-appointed. It is easy to get to, and central to both sides of town.

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Seashore getaway - CT shoreline
Thanks Lauren! We enjoyed your lovely place!
Pet-friendly condo rentals

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Beautiful 2 bedrooms/ 2 bath Condo
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr
This was our second stay at Dariel’s place. It is perfect for our family and I always check to see if it is available when we are visiting the area. It is spacious yet cozy, and well-appointed. It is easy to get to, and central to both sides of town.

Lovely 2-Bedroom Condo on Historic Wooster Street
The host was incredibly responsive and helpful. The house was clean, exactly as described, and in a fantastic central location. A great value, exactly what my family was looking for this weekend in New Haven. Highly recommended, easiest 5 stars I've given in awhile.

Chateau Blanc Yale
Our stay was a wonderful experience. The host was very helpful and accommodating. Would stay here again! 10 out of 10.

Stylish Downtown Hartford|Laundry|ConventionCenter
The next time I plan to visit Connecticut, I will definitely consider staying here again. The location was fantastic, offering beautiful views of downtown Hartford. It was a peaceful area with friendly neighbors, and the front desk staff was incredibly helpful. The only downside I encountered was that when I first walked into the apartment, it had a musty smell in the hallway due to a lack of air fresheners, and the TV remote wasn't working. However, after I reached out to the staff about the issues, I received new batteries and a wall plug from his assistant in less than 10 minutes. Unfortunately, the remote still didn’t work, so I ended up using the Roku remote on my phone. Coming from a real estate background, I’d say the place is a bit overpriced, mainly due to the building’s condition; it feels somewhat rundown. Still, I’d rate it a solid 8.8 out of 10 overall. Brain thanks for hosting me.

Charming Studio| Near Yale| Downtown New Haven
An impeccable stay, so much so that I’m actually sad to leave. A very convenient location that is a five minute walk from the campus, and anything else is extremely close by. Clear and efficient communication, clean and organized space, will 100% stay again
Condo rentals with a pool

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Seashore getaway - CT shoreline
Thanks Lauren! We enjoyed your lovely place!

Beautiful 2 bedrooms/ 2 bath Condo
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.
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- Beach
- Misquamicut State Beach
- Fairfield Beach
- Hammonasset Beach
- Ocean Beach
- Yale University
- Pleasure Beach
- Soundview Beach
- Watch Hill Beach Association Beach
- Dunes Park Beach
- Rocky Neck State Park Bathing Beach
- Stony Creek Beach
- Weekapaug Inn Beach
- Sea Bluff Beach
- Foxwoods Resort Casino
- Limewood Beach
- Esker Point Beach
- Maidstone Park Beach
- Halsey Neck Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Six Flags New England
- Quotonset Beach
- Walnut Public Beach