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Holiday Rentals in Middlesex County
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Our top choices for Middlesex County holiday rentals
Cabin in East Haddam
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy9.6 out of 10, Exceptional, (93)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
Keven
The price is €139
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage in Clinton
1-bedroom cottage with Grove Beach 🏖️ access.9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
Deb P.
The price is €182
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Home in Middletown
#24 *Serenity* A Lakefront Cottage Retreat9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
Nichole N.
The price is €492
includes taxes & fees
31 Dec - 1 Jan 2026
10.0 out of 10, Exceptional, (27)
"Spacious, quiet and comfortable. "
Elizabeth M.
The price is €224
includes taxes & fees
1 Jan - 2 Jan 2026
Apartment in East Haddam
Walk To Goodspeed Opera House!9.4 out of 10, Exceptional, (34)
"The place was spotless and comfortable. Would highly recommend!"
Jeanne Y.
The price is €222
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Middletown
Family Stays: Middletown, CT10.0 out of 10, Exceptional, (19)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
Cari M.
The price is €207
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Home in Middletown
Cozy Guest Suite in Historic Home10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
Brooke
The price is €188
includes taxes & fees
3 Jan - 4 Jan 2026
Apartment in Washington Street Historic District
Apartment in Middletown-Wesleyan 102The price is €273
includes taxes & fees
19 Jan - 20 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Middlesex County Hotel Reviews
Hilton Garden Inn Preston Casino Area
10/10 Excellent
Find out more about Middlesex County
Holiday Homes in Middlesex County
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