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Search and Rent Middletown Condos

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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Middletown

Breakfast, lunch, dinner served; American cuisine
Inn at Middletown

Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (543)
"The Inn was very nice!"
United States
Traci
$186 nightly
The price is $210
Dec 23 - Dec 24
Total with taxes and fees
Inn at Middletown
Property grounds
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
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. "
United States
Nichole N.
$536 nightly
The price is $588
Dec 31 - Jan 1, 2026
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
Family Stays: Middletown, CT

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
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!"
United States
Cari M.
$209 nightly
The price is $237
Jan 6 - Jan 7, 2026
Total with taxes and fees
Family Stays: Middletown, CT
Interior
Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
$190 nightly
The price is $215
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy Guest Suite in Historic Home
Smart TV
#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6)
"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.
$526 nightly
The price is $569
Dec 28 - Dec 29
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
Dining
Apartment in Middletown-Wesleyan 102

Apartment in Middletown-Wesleyan 102

Apartment in Middletown-Wesleyan 102
2.0 star property
Washington Street Historic District
$276 nightly
The price is $313
Jan 13 - Jan 14, 2026
Total with taxes and fees
Apartment in Middletown-Wesleyan 102
Smart TV
3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
6.6 out of 10, (4)
"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.
$170 nightly
The price is $193
Dec 29 - Dec 30
Total with taxes and fees
3-bedroom Unit in tranquil Middletown
Fridge, microwave, oven, stovetop
Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
6.0 out of 10, (2)
"The apartment was exactly what we needed to rest between events at Wesleyan. Good communication, fixed an air conditioner and added one prior to our arrival (and it was very very hot. So it was appreciated."
United States
Carolyn O.
$264 nightly
The price is $299
Jan 13 - Jan 14, 2026
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
Free buffet breakfast
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
2.5 star property
Southington
8.6 out of 10, Excellent, (1175)
"The place was great. enjoyed our stay."
United States
Michael
$82 nightly
The price is $94
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn Express Southington by IHG
Free daily continental breakfast
Spark by Hilton Guilford

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (68)
"Comfortable beds, friendly staff "
United States
Taylor
$104 nightly
The price is $120
Jan 3 - Jan 4, 2026
Total with taxes and fees
Spark by Hilton Guilford
Lobby
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
Waterbury
8.4 out of 10, Very Good, (1073)
"The staff were amazing,The rooms were very clean,when ever i'm in town this is were I always stay. thank you to the staff for all you do to always make my stay comfortable."
United States
Diana
$89 nightly
The price is $102
Dec 28 - Dec 29
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 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 😊"
United States
Keven
$141 nightly
The price is $162
Jan 4 - Jan 5, 2026
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1007)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
$69 nightly
The price is $79
Dec 28 - Dec 29
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Lobby
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
2.5 star property
Berlin
8.6 out of 10, Excellent, (1001)
"great stay."
United States
John
$87 nightly
The price is $100
Jan 2 - Jan 3, 2026
Total with taxes and fees
Best Western Plus New England Inn & Suites
Lobby sitting area
New Haven Hotel

New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven
9.0 out of 10, Wonderful, (1948)
"Location, friendly staff, clean a comfortable room. Will stay again!"
United States
Kim
$97 nightly
The price is $112
Dec 30 - Dec 31
Total with taxes and fees
New Haven Hotel
Individually decorated, individually furnished, desk, laptop workspace
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (462)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveler
$67 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford
2.5 star property
East Hartford
9.0 out of 10, Wonderful, (1090)
"We enjoyed our visit "
United States
Richard
$98 nightly
The price is $112
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hampton Inn & Suites Hartford/East Hartford
Property amenity
Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor
3.0 star property
South Windsor
9.2 out of 10, Wonderful, (844)
"The room was very clean. I love that there was no carpeting. Great room!"
Canada
Nissa
$125 nightly
The price is $144
Jan 2 - Jan 3, 2026
Total with taxes and fees
Cambria Hotel Manchester South Windsor
Exterior
Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG
2.5 star property
Rocky Hill
8.6 out of 10, Excellent, (1004)
"The hotel is convenient to the highway and local dining. "
United States
NAVRAJ
$93 nightly
The price is $107
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Hartford South - Rocky Hill by IHG
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (912)
"Great place stayed several times."
United States
Marlene D
$96 nightly
The price is $110
Jan 2 - Jan 3, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Place was very clean and well put together just in a bad area "
Olajuwon 1-night trip
Posted 10 hours ago
Courtyard by Marriott Waterbury Downtown

Find out more about Middletown

Middletown Condo Rentals information

Number of reviews
11,249
Accommodation
16 Condo Rentals
Lowest Price
$77
Highest Price
$588

Frequently asked questions

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How can I find cheap condos in Middletown?
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What is there to do in Middletown near my condo?
The most practical travel accessory is a well-planned to-do list. Kidcity Children's Museum is a good place to kick off your exploration of Middletown.

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