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

Search Holiday Homes in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Middletown holiday homes

Property grounds

1. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
#24 *Serenity* A Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

2. “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 £213
includes taxes & fees
17 Sept - 18 Sept
“3BR Home Near Wesleyan & Downtown Middletown
Exterior

3. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is £627
includes taxes & fees
16 Sept - 17 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Interior

4. Belltown House at Airline Trail

Belltown House at Airline Trail
East Hampton
The price is £339
includes taxes & fees
9 Sept - 10 Sept
Belltown House at Airline Trail
Coffee/tea maker, fridge, microwave, oven

5. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
The price is £342
includes taxes & fees
14 Sept - 15 Sept
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Iron/ironing board, WiFi, bed sheets

6. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is £474
includes taxes & fees
25 Aug - 26 Aug
The Cottage by the Woods -private getaway to relax
1 bedroom, iron/ironing board, WiFi, bed sheets

7. 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 £222
includes taxes & fees
30 Aug - 31 Aug
Once the old Schools house now a newly furnished Apartment
Interior

8. 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 £768
includes taxes & fees
20 Aug - 21 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Smart TV

9. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is £108
includes taxes & fees
8 Sept - 9 Sept
Entire guest suite in South Windsor, Connecticut
Coffee/tea maker, fridge, microwave, oven

10. #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 £443
includes taxes & fees
19 Aug - 20 Aug
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

11. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is £367
includes taxes & fees
31 Aug - 1 Sept
Cozy basement apartment with private bathroom, kitchen and entrance.
Dining

12. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is £395
includes taxes & fees
14 Sept - 15 Sept
Prime West Hartford Center: Timeless Charm
Interior

13. #22- 4 Br 2 Ba house-Central CT

#22- 4 Br 2 Ba house-Central CT
New Britain
The price is £329
includes taxes & fees
21 Aug - 22 Aug
#22- 4 Br 2 Ba house-Central CT
Interior

14. 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 £223
includes taxes & fees
31 Aug - 1 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV

15. 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, (28 reviews)
"Was a great stay"
United States
John S.
The price is £235
includes taxes & fees
9 Sept - 10 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Dining

16. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is £234
includes taxes & fees
19 Aug - 20 Aug
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
TV, fireplace

17. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is £296
includes taxes & fees
19 Aug - 20 Aug
Willow Haven 2BR Cozy Retreat, Close to Hartford
TV, books

18. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is £396
includes taxes & fees
19 Aug - 20 Aug
The Game House Arcade – West Hartford
TV, fireplace

19. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is £473
includes taxes & fees
26 Aug - 27 Aug
#41- Available 12/8! - sleeps 14
Dining

20. Summer is filling up-Beach, Shopping and Golf

Summer is filling up-Beach, Shopping and Golf
Clinton
10.0 out of 10, Exceptional, (5 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is £526
includes taxes & fees
19 Aug - 20 Aug
Summer is filling up-Beach, Shopping and Golf
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Very friendly environment, helpful staff and clean room, worth the money spent and excellent experience"
Danny 1-night trip
Posted 10 hours ago
Holiday Inn Cheshire - Southington by IHG

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
140
Accommodation
349 Holiday Homes
Lowest Price
£108
Highest Price
£768