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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Middletown holiday homes

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "
United States
Robb F.
The price is £238
includes taxes & fees
22 Feb - 23 Feb
#24 *Serenity* A Lakefront Cottage Retreat
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 £165
includes taxes & fees
24 Feb - 25 Feb
Family Stays: Middletown, CT
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 £159
includes taxes & fees
17 Feb - 18 Feb
Cozy Guest Suite in Historic Home
Smart TV

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is £307
includes taxes & fees
2 Mar - 3 Mar
#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 £161
includes taxes & fees
17 Feb - 18 Feb
3-bedroom Unit in tranquil Middletown
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is £308
includes taxes & fees
17 Feb - 18 Feb
Welcoming 4-bedroom house in charming Hamden
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is £378
includes taxes & fees
21 Feb - 22 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is £233
includes taxes & fees
18 Feb - 19 Feb
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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 £390
includes taxes & fees
10 Mar - 11 Mar
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (4 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is £523
includes taxes & fees
17 Feb - 18 Feb
Stylish Townhome | Perfect for Family Gatherings & Events
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 £468
includes taxes & fees
17 Feb - 18 Feb
Rogers Lake House (87) · CT College+Beach+USCGA
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, (16 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is £209
includes taxes & fees
23 Feb - 24 Feb
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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 £206
includes taxes & fees
2 Mar - 3 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
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 £201
includes taxes & fees
18 Feb - 19 Feb
Private Apartment in Berlin
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, (19 reviews)
"Great value very close to university. "
United States
Lawrence
The price is £165
includes taxes & fees
17 Feb - 18 Feb
Stocked home close to Yale, in Heart of New Haven
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 £246
includes taxes & fees
18 Feb - 19 Feb
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 £180
includes taxes & fees
23 Feb - 24 Feb
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Microwave, oven, stovetop, dishwasher

One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.
Rocky Hill
The price is £113
includes taxes & fees
17 Feb - 18 Feb
One private bedroom with work space and shared home with spa.
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 £195
includes taxes & fees
3 Mar - 4 Mar
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
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!
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 £358
includes taxes & fees
22 Feb - 23 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Great amenities, Beautiful view, and Caring Staff. "
Janine Louise 3-night trip
Posted 5 days ago
Water's Edge Resort & Spa

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
143
Accommodation
356 Holiday Homes
Lowest Price
£113
Highest Price
£523