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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Middletown vacation homes

Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ￥23,408
￥34,056 total
includes taxes & fees
Jan 20 - Jan 21
Cozy Guest Suite in Historic Home
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
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 ￥19,824
￥37,546 total
includes taxes & fees
Feb 1 - Feb 2
Family Stays: Middletown, CT
Smart TV

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
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 ￥33,769
￥74,676 total
includes taxes & fees
Jan 31 - Feb 1
#29 - Modern 5 Bedroom/2 Bath
Smart TV

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
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 ￥26,960
￥34,493 total
includes taxes & fees
Jan 26 - Jan 27
3-bedroom Unit in tranquil Middletown
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
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 ￥13,694
￥63,858 total
includes taxes & fees
Jan 20 - Jan 21
Rogers Lake House (87) · CT College+Beach+USCGA
Interior

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥15,329
￥57,642 total
includes taxes & fees
Jan 19 - Jan 20
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
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 ￥16,018
￥46,729 total
includes taxes & fees
Jan 18 - Jan 19
Private Apartment in Berlin
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
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 ￥19,189
￥44,904 total
includes taxes & fees
Jan 20 - Jan 21
Modern & Cozy Cape | 4 Bedroom House | Central Location
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
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 ￥19,713
￥77,582 total
includes taxes & fees
Jan 21 - Jan 22
Beachside Bliss w/ Game Room, Gym & Golf Green
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
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 ￥23,693
￥86,124 total
includes taxes & fees
Jan 19 - Jan 20
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Dining

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Manchester
9.8 out of 10, Exceptional, (10 reviews)
"Very clean and super comfortable. Would stay here again."
United States
vanessa c.
The price is ￥15,542
￥39,600 total
includes taxes & fees
Jan 21 - Jan 22
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
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 ￥18,238
￥45,714 total
includes taxes & fees
Jan 18 - Jan 19
Once the old Schools house now a newly furnished Apartment
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
The price is ￥10,562
￥15,318 total
includes taxes & fees
Jan 25 - Jan 26
Entire guest suite in South Windsor, Connecticut
Fridge, microwave, oven, stovetop

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
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 ￥13,829
￥78,364 total
includes taxes & fees
Jan 25 - Jan 26
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
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 ￥28,546
￥57,251 total
includes taxes & fees
Jan 18 - Jan 19
Stylish Modern Stay Steps from the Ocean
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is ￥20,300
￥38,252 total
includes taxes & fees
Jan 19 - Jan 20
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Property grounds

Charming Lakeview, 3 Bedroom home in Colchester

Charming Lakeview, 3 Bedroom home in Colchester
Colchester
10.0 out of 10, Exceptional, (1 review)
"Property was perfect for our Christmas break - very clean and tidy, had everything needed. Beds are comfortable and rooms feel spacious. Check-in was a breeze. Water pressure is a little low in the shower but the owners are aware of the issue. You can't go wrong with staying here!"
United States
Meagan P.
The price is ￥33,304
￥63,674 total
includes taxes & fees
Feb 13 - Feb 14
Charming Lakeview, 3 Bedroom home in Colchester
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
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 ￥18,872
￥44,381 total
includes taxes & fees
Jan 25 - Jan 26
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (18 reviews)
"Great value very close to university. "
United States
Lawrence
The price is ￥23,551
￥39,986 total
includes taxes & fees
Jan 18 - Jan 19
Stocked home close to Yale, in Heart of New Haven
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
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 ￥16,799
￥35,178 total
includes taxes & fees
Jan 25 - Jan 26
#26 Beautifully Renovated 2 BR Home
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"The room was drafty around the heating unit. Additionally, this hotel, like most newly built hotels, uses an automatic thermostat for the heat and cool. When the thermostat is set and it gets a little too warm in the room, and you turn it down a couple degrees the AC kicks on rather than just allowing the ambient temp drop. When the outside temp is 18 degrees having the AC running is not a pleasant experience. Overall, this is a really nice place to stay. Staff is friendly and its clean."
Mark 4-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
103
Accommodation
356 Vacation Homes
Lowest Price
￥34,056
Highest Price
￥86,124