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Our top choices for Middletown holiday homes

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is HK$1,151
HK$1,674 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Guest Suite in Historic Home
9.8 out of 10, Exceptional, (21 reviews)
"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. "
United States
Nichole N.
The price is HK$1,185
HK$2,642 total
includes taxes & fees
18 Feb - 19 Feb
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$975
HK$1,846 total
includes taxes & fees
1 Feb - 2 Feb
Family Stays: Middletown, CT

Holiday Home in Middletown

#29 - Modern 5 Bedroom/2 Bath
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful home and well suited for a peaceful stay. Great neighborhood and a wonderful how. Would recommend the property to anyone."
United States
LaToya O.
The price is HK$1,660
HK$3,671 total
includes taxes & fees
31 Jan - 1 Feb
#29 - Modern 5 Bedroom/2 Bath

Holiday Home in Washington Street Historic District

3-bedroom Unit in tranquil Middletown
6.6 out of 10, (4 reviews)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
United States
Jenn U.
The price is HK$1,325
HK$1,696 total
includes taxes & fees
26 Jan - 27 Jan
3-bedroom Unit in tranquil Middletown

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5 reviews)
"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! "
United States
Daniel L.
The price is HK$709
HK$2,207 total
includes taxes & fees
20 Jan - 21 Jan
Private Apartment in Berlin
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is HK$754
HK$2,834 total
includes taxes & fees
21 Jan - 22 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$673
HK$3,140 total
includes taxes & fees
3 Feb - 4 Feb
Rogers Lake House (87) · CT College+Beach+USCGA
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$905
HK$3,928 total
includes taxes & fees
20 Jan - 21 Jan
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is HK$943
HK$2,208 total
includes taxes & fees
20 Jan - 21 Jan
Modern & Cozy Cape | 4 Bedroom House | Central Location
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,089
HK$3,945 total
includes taxes & fees
20 Jan - 21 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$680
HK$3,853 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is HK$1,403
HK$2,815 total
includes taxes & fees
20 Jan - 21 Jan
Stylish Modern Stay Steps from the Ocean
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$897
HK$2,247 total
includes taxes & fees
20 Jan - 21 Jan
Once the old Schools house now a newly furnished Apartment
2.0 star property
The price is HK$519
HK$753 total
includes taxes & fees
25 Jan - 26 Jan
Entire guest suite in South Windsor, Connecticut
9.4 out of 10, Exceptional, (15 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$928
HK$2,182 total
includes taxes & fees
25 Jan - 26 Jan
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
The price is HK$717
HK$1,071 total
includes taxes & fees
20 Jan - 21 Jan
One private bedroom with work space and shared home with spa.
2.0 star property
The price is HK$1,784
HK$3,315 total
includes taxes & fees
20 Jan - 21 Jan
Welcoming 4-bedroom house in charming Hamden

Holiday Home in Plainville

#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$826
HK$1,730 total
includes taxes & fees
25 Jan - 26 Jan
#26 Beautifully Renovated 2 BR Home
9.6 out of 10, Exceptional, (134 reviews)
"We loved our stay!"
United States
Deana L.
The price is HK$1,559
HK$4,023 total
includes taxes & fees
20 Jan - 21 Jan
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
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 Middletown Hotel Reviews

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
179
Accommodation
356 Vacation Homes
Lowest Price
HK$1,071
Highest Price
HK$4,023

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