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 NZ$574
includes taxes & fees
22 July - 23 July
#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 NZ$479
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 NZ$543
includes taxes & fees
22 July - 23 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 NZ$903
includes taxes & fees
11 Aug - 12 Aug
#29 - Modern 5 Bedroom/2 Bath
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
1 Min to I-91 - Newly Renovated Modern 2 BR Home
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 NZ$494
includes taxes & fees
1 Aug - 2 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
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 NZ$494
includes taxes & fees
1 Aug - 2 Aug
Once the old Schools house now a newly furnished Apartment
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 NZ$1,769
includes taxes & fees
1 Aug - 2 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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 NZ$853
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 NZ$846
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 NZ$1,055
includes taxes & fees
22 July - 23 July
#41- Available 12/8! - sleeps 14
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 NZ$560
includes taxes & fees
22 July - 23 July
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
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is NZ$550
includes taxes & fees
27 July - 28 July
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.
The price is NZ$754
includes taxes & fees
3 Aug - 4 Aug
Lakefront Home, Close to Mt Southington!
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 NZ$204
includes taxes & fees
3 Aug - 4 Aug
Entire guest suite in South Windsor, Connecticut
Interior

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

Spacious 4-Bedroom Home for Groups & Families — Minutes from Hartford
East Hartford
8.0 out of 10, Very good, (4 reviews)
"Great place to stay the nites"
United States
John S.
The price is NZ$794
includes taxes & fees
2 Aug - 3 Aug
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, (52 reviews)
"Everything was perfect! "
United States
Melissa R.
The price is NZ$657
includes taxes & fees
27 July - 28 July
Peek-A-Boo View, Amston Lake
Dining

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
10.0 out of 10, Exceptional, (1 review)
"The host was extremely accommodating and reached out to address every need Very good stay for the price. Will book again if I ever need to. Close to anything that you need."
United States
Ismael P.
The price is NZ$192
includes taxes & fees
27 July - 28 July
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (1 review)
"House was clean and very good communication with owners. I put 4 stars only because there was only one television which some families might not mind but was t a deal breaker we bought one and made it work. Also only window unit which is not shown in the photos so it was really cold in the front of the home vs. bedrooms but again not a deal breaker. Beautiful nature outside rabbits woodchuck birds raccoon & skunk!!! very convenient location close to grocery not far from restaurants, etc."
United States
Dionne V.
The price is NZ$699
includes taxes & fees
22 July - 23 July
Willow Haven 2BR Cozy Retreat, Close to Hartford
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$729
includes taxes & fees
22 July - 23 July
Adorable Cottage, 5 min walk to water & town
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

8/10 Good
"We loved the hot breakfast! Rooms were clean but not immaculate."
Elizabeth 1-night trip
Posted 4 hours ago
Holiday Inn Express Southington by IHG

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
275
Accommodation
365 Holiday Homes
Lowest Price
NZ$192
Highest Price
NZ$1,769