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

Holiday Homes in Middletown

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Our top choices for Middletown holiday homes

1. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is €234
includes taxes & fees
1 Dec - 2 Dec
Family Stays: Middletown, CT

2. #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 €382
includes taxes & fees
3 Nov - 4 Nov
#29 - Modern 5 Bedroom/2 Bath

3. 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, (35 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 €1,036
includes taxes & fees
3 Nov - 4 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

4. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is €445
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

5. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €270
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is €588
includes taxes & fees
3 Nov - 4 Nov
The Cottage by the Woods -private getaway to relax

7. #22- 4 Br 2 Ba house-Central CT

#22- 4 Br 2 Ba house-Central CT
New Britain
9.0 out of 10, Wonderful, (2 reviews)
"Host was great and responsive and the property was perfect for what we needed."
United States
Hilda C.
The price is €394
includes taxes & fees
7 Nov - 8 Nov
#22- 4 Br 2 Ba house-Central CT

8. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is €102
includes taxes & fees
3 Nov - 4 Nov
Entire guest suite in South Windsor, Connecticut

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is €405
includes taxes & fees
3 Nov - 4 Nov
Cozy basement apartment with private bathroom, kitchen and entrance.

10. 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 €364
includes taxes & fees
3 Nov - 4 Nov
The Game House Arcade | West Hartford

11. 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, (31 reviews)
"Was a great stay"
United States
John S.
The price is €267
includes taxes & fees
8 Nov - 9 Nov
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

12. #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 €433
includes taxes & fees
22 Nov - 23 Nov
#27- Luxury Collection

13. Prime West Hartford Center | Timeless Charm

Prime West Hartford Center | Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (27 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 €423
includes taxes & fees
3 Nov - 4 Nov
Prime West Hartford Center | Timeless Charm

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 €261
includes taxes & fees
3 Nov - 4 Nov
Modern & Cozy Cape | 4 Bedroom House | Central Location

15. 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 €127
includes taxes & fees
19 Nov - 20 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

16. 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
The price is €408
includes taxes & fees
3 Nov - 4 Nov
Charming New England Home in West Hartford Center

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

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is €267
includes taxes & fees
3 Nov - 4 Nov
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

18. #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 €592
includes taxes & fees
22 Nov - 23 Nov
#30 - Spacious & Cozy!

19. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €289
includes taxes & fees
3 Nov - 4 Nov
Bear Retreat - 2-bedroom house in Waterbury

20. 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, (12 reviews)
"Place is nice would stay again "
United States
nic
The price is €365
includes taxes & fees
17 Nov - 18 Nov
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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

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Middletown Holiday Homes information

Number of reviews
233
Accommodation
341 Holiday Homes
Lowest Price
€102
Highest Price
€1,036