
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.
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Popular amenities for Middletown condo rentals
Weekly condo rentals

The Anchor at Soundview · Beach+Ocean+Sunrise
Nice place, nice people relaxing vibe comfortable bed tons of free movies

Newly Renovated Villa with King Bed at Norwich Spa
Place was just as described, will gladly return for another stay. Good location lots to find to do.

Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
Very clean and nicely decorated condo for our enjoyable weekend getaway. Would love to stay here again!

Freeboard at Soundview · Beach+Ocean+Sunrise
Rate was great, it was off season. Cleaning fee is a little nutz considering it is tiny. VERY clean, perfectly functional. I wasn't a fan of the mattress, way too soft for me, but maybe that is just me :-) Overall I would happily stay there again. It was quiet, the other tenants were very friendly.

Cliffside Resort Poolside Condo A101
Really liked the place but our reservation didn’t end up getting entered into the Cliffside system - so I had to call the after hours emergency service to get the code to get in. Not a huge deal but a little scary,

Near Casino-2 Beds-Heated Pool/Jacuzzi/Sauna-Spa
Super cool villa so close to Mohegan. Beds were very comfortable and it was the easiest check in and entry! Loved the decor and vibe of the place!

City Centre Crash Pad
Great condo, spacious and well maintained. Everything available that you need. I was not able to stay overnight due to a family urgency but no issues with the space, paid parking lots close by and very walkable area with a nice park nearby!
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!

Entire house - 4 Bedroom-Enfield
Everything I needed for my work trip👍👍👍 Clean and cozy stay

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.

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

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.

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

Modern Loft Villa, 1 mile to Mohegan Sun
We had a wonderful stay. The house was beautiful and clean and had everything we needed. Erin was so easy to communicate with. I would recommend this house for anyone visiting the area.

Beautiful condo on Long Islands Northfolk
This was the perfect last-minute getaway for my always on-the-go family in need of some quiet bonding time. The condo was simple and clean, the beach beautiful (even in the winter), and Alice and Gasper were very responsive. Would highly recommend!

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!

Cozy Vacation Villa 5 minutes from Mohegan
My husband and I stayed at Desiree’s place for New Years weekend. The space was beautiful, clean, comfortable and perfect for our getaway. Close to the casino and spa and anything you need. Would definitely recommend!

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi
Amazing stay!! Beautiful home, clean, had everything we needed. Quiet place as well!! Only thing the heated outdoor pool was closed due to maintenance during our stay, but everything else was perfect! Will definitely be staying again!!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

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

Mohegan Sun Escape-Hot Tub/Pool/Golf & Norwich Spa
The condo was beautiful, very clean and had many extras one wouldn't have expected. The owner put a lot of thought and detail to providing little extras for renters. I liked the location of the condo very easy to get to. I had an awesome weekend right next to the Norwich Spa and close to Mohegan and Foxwoods! I would definitely recommend this place and return in the future. Nat was a perfect host! Thank you for everything! Gai
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Six Flags New England
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Thunder Ridge Ski Area
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Mohawk Mountain Ski Area
- Bushnell Park
- Sherwood Island State Park