Holiday Homes in Middletown

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

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, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is €358
includes taxes & fees
19 May - 20 May
#24 *Serenity* A Lakefront Cottage Retreat
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 €401
includes taxes & fees
7 May - 8 May
#29 - Modern 5 Bedroom/2 Bath
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, (22 reviews)
"Great place"
United States
John S.
The price is €274
includes taxes & fees
4 May - 5 May
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is €306
includes taxes & fees
29 Apr - 30 Apr
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
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
The price is €369
includes taxes & fees
11 May - 12 May
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (2 reviews)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is €402
includes taxes & fees
29 Apr - 30 Apr
Welcoming 4-bedroom house in charming Hamden
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
7.6 out of 10, Good, (4 reviews)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is €531
includes taxes & fees
29 Apr - 30 Apr
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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 €254
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment
Smart TV

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
West Hartford
7.8 out of 10, Good, (11 reviews)
"everything was good but there was a few things that needed fix up on I contacted the host and let them know about a few things and so on other then that i enjoyed my stay "
United States
Shaheym J.
The price is €287
includes taxes & fees
3 May - 4 May
Charming 3-Bedroom Home with Modern Comforts in West Hartford
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 €224
includes taxes & fees
4 May - 5 May
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
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, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is €547
includes taxes & fees
6 May - 7 May
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is €680
includes taxes & fees
5 May - 6 May
Heavenly Home in New Haven /5 mins drive from Yale
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (64 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is €450
includes taxes & fees
14 May - 15 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is €193
includes taxes & fees
29 Apr - 30 Apr
Stocked home close to Yale, in Heart of New Haven
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is €106
includes taxes & fees
10 May - 11 May
Entire guest suite in South Windsor, Connecticut
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, (8 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 €264
includes taxes & fees
12 May - 13 May
Modern & Cozy Cape | 4 Bedroom House | Central Location
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, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
Rogers Lake House (87) · CT College+Beach+USCGA
Interior

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
The price is €118
includes taxes & fees
30 Apr - 1 May
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is €427
includes taxes & fees
5 May - 6 May
Cozy basement apartment with private bathroom, kitchen and entrance.
Fridge, microwave, oven, stovetop

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is €442
includes taxes & fees
29 Apr - 30 Apr
#27- Luxury Collection
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

The Capitol Hotel

The Capitol Hotel

6/10 Okay
"Lots of little crusty bits in the corners of the rooms. Hot breakfast was not hot and tasted stale, as if it had been re-heated (but only partially, because, as I said, it was not hot)."
Andrew 2-night trip
Posted 5 hours ago
The Capitol Hotel

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
233
Accommodation
341 Holiday Homes
Lowest Price
€106
Highest Price
€680