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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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.
The price is €300
includes taxes & fees
20 Sept - 21 Sept
#24 Serenity A Lakefront Cottage Retreat
Exterior

2. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is €207
includes taxes & fees
12 Oct - 13 Oct
Family Stays: Middletown, CT
Living area

3. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is €419
includes taxes & fees
23 Sept - 24 Sept
#29 - Modern 5 Bedroom/2 Bath
Exterior

4. 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
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is €722
includes taxes & fees
29 Sept - 30 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Living area

5. 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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is €264
includes taxes & fees
20 Sept - 21 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
Room

6. 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 €264
includes taxes & fees
21 Sept - 22 Sept
Once the old Schools house now a newly furnished Apartment
Room

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is €560
includes taxes & fees
18 Sept - 19 Sept
The Cottage by the Woods -private getaway to relax
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
10.0 out of 10, Exceptional, (31 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is €907
includes taxes & fees
20 Sept - 21 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Private kitchen

9. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
#26 Beautifully Renovated 2 BR Home
Interior

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is €415
includes taxes & fees
29 Sept - 30 Sept
Cozy basement apartment with private bathroom, kitchen and entrance.
Living area

11. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is €466
includes taxes & fees
20 Sept - 21 Sept
#41- Available 12/8! - sleeps 14
Living area

12. 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, (30 reviews)
"Was a great stay"
United States
John S.
The price is €268
includes taxes & fees
20 Sept - 21 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Interior

13. 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 €256
includes taxes & fees
20 Sept - 21 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Living area

14. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is €107
includes taxes & fees
29 Sept - 30 Sept
Entire guest suite in South Windsor, Connecticut
Living area

15. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is €426
includes taxes & fees
23 Sept - 24 Sept
#30 - Spacious & Cozy!
Dining

16. 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 €464
includes taxes & fees
13 Oct - 14 Oct
Prime West Hartford Center: Timeless Charm
Living area

17. 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 €424
includes taxes & fees
20 Sept - 21 Sept
The Game House Arcade – West Hartford
Terrace/patio

18. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
Charming New England Home in West Hartford Center
Interior

19. 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
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is €131
includes taxes & fees
20 Sept - 21 Sept
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Private kitchen

20. #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 €396
includes taxes & fees
5 Oct - 6 Oct
#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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."
John 1-night trip
Posted 3 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
203
Accommodation
349 Holiday Homes
Lowest Price
€107
Highest Price
€907