A forested landscape with a winding dirt road and power lines.

Holiday Homes in Middletown

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

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)
"It was great "
United States
Rodrigo C.
The price is AU$528
includes taxes & fees
5 Aug - 6 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (29 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is AU$407
includes taxes & fees
10 Aug - 11 Aug
Family Stays: Middletown, CT
Coffee/tea maker, fridge, microwave, oven

“3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is AU$459
includes taxes & fees
27 July - 28 July
“3BR Home Near Wesleyan & Downtown Middletown
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 AU$733
includes taxes & fees
11 Aug - 12 Aug
#29 - Modern 5 Bedroom/2 Bath
Interior

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is AU$1,425
includes taxes & fees
26 July - 27 July
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$419
includes taxes & fees
26 July - 27 July
Once the old Schools house now a newly furnished Apartment
TV

Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is AU$419
includes taxes & fees
1 Aug - 2 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
Coffee/tea maker, fridge, microwave, oven

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is AU$649
includes taxes & fees
28 July - 29 July
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is AU$698
includes taxes & fees
27 July - 28 July
Cozy basement apartment with private bathroom, kitchen and entrance.
TV, fireplace

#41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AU$767
includes taxes & fees
28 July - 29 July
#41- Available 12/8! - sleeps 14
Interior

Spacious 4-Bedroom Home for Groups & Families — Minutes from Hartford

Spacious 4-Bedroom Home for Groups & Families — Minutes from Hartford
East Hartford
8.4 out of 10, Very good, (5 reviews)
"Great place to stay the nites"
United States
John S.
The price is AU$650
includes taxes & fees
26 July - 27 July
Spacious 4-Bedroom Home for Groups & Families — Minutes from Hartford
Terrace/patio

Peek-A-Boo View, Amston Lake

Peek-A-Boo View, Amston Lake
Lebanon
9.8 out of 10, Exceptional, (53 reviews)
"Everything was perfect! "
United States
Melissa R.
The price is AU$542
includes taxes & fees
27 July - 28 July
Peek-A-Boo View, Amston Lake
Outdoor dining

Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (34 reviews)
"Everything was perfect! Amazing place to stay."
United States
J
The price is AU$1,084
includes taxes & fees
9 Aug - 10 Aug
Prime West Hartford Center Location: Historic Gem
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is AU$436
includes taxes & fees
25 Aug - 26 Aug
Modern & Cozy Cape | 4 Bedroom House | Central Location
Property grounds

Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
Wolcott
10.0 out of 10, Exceptional, (33 reviews)
"The place was a haven. Lovely home away from home. More than met my expectations. "
United States
Margaret W.
Lakefront Home, Close to Mt Southington!
Smart TV

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

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (26 reviews)
"Was a great stay"
United States
John S.
The price is AU$487
includes taxes & fees
30 July - 31 July
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Property grounds

Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (28 reviews)
"This place is a gem! It's very spacious. Beautiful views of the lake that is right outside your door. The kitchen is fully stocked with everything you need, if cooking. We found it very clean when we arrived. It's a comfortable place to stay. Will stay again. "
United States
Jean B.
The price is AU$673
includes taxes & fees
16 Aug - 17 Aug
Spacious modern home on private lake
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, (11 reviews)
"Place is nice would stay again "
United States
nic
The price is AU$674
includes taxes & fees
27 July - 28 July
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (6 reviews)
"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 AU$174
includes taxes & fees
27 July - 28 July
Entire guest suite in South Windsor, Connecticut
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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$758
includes taxes & fees
30 July - 31 July
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Hotel was great."
Shiva 1-night trip
Posted 1 hour ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
400
Accommodation
359 Holiday Homes
Lowest Price
AU$174
Highest Price
AU$1,425