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Our top choices for Cheshire Historic District vacation homes
#24 *Serenity* A Lakefront Cottage Retreat
#24 *Serenity* A Lakefront Cottage RetreatMiddletown
9.8 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.
$299 nightly
The price is $320
Dec 22 - Dec 23
Total with taxes and fees
Cozy Guest Suite in Historic Home
Cozy Guest Suite in Historic HomeMiddletown
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
Brooke
$190 nightly
The price is $215
Jan 3 - Jan 4, 2026
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
#26 Beautifully Renovated 2 BR HomePlainville
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
LaTanya W.
$222 nightly
The price is $239
Jan 5 - Jan 6, 2026
Total with taxes and fees
Family Stays: Middletown, CT
Family Stays: Middletown, CTMiddletown
10.0 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.
$209 nightly
The price is $237
Jan 6 - Jan 7, 2026
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Once the old Schools house now a newly furnished ApartmentWallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
Jeanette W.
$271 nightly
The price is $288
Jan 2 - Jan 3, 2026
Total with taxes and fees
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
Daniel L.
$265 nightly
The price is $300
Jan 11 - Jan 12, 2026
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, GarageNew Britain
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
Elizabeth P.
$218 nightly
The price is $246
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
Cozy East Haven Home • Near Beach & YaleMomauguin
10.0 out of 10, Exceptional, (4)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
Amal A.
$145 nightly
The price is $164
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
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Top Cheshire Historic District Hotel Reviews
New Haven Hotel
10/10 Excellent
Find out more about Cheshire Historic District
Cheshire Historic District Vacation Homes information
Number of reviews | 138 |
|---|---|
Accommodation | 213 Vacation Homes |
Lowest Price | $164 |
Highest Price | $513 |
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