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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Middletown vacation homes

1. 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 ￥21,095
￥38,948 total
includes taxes & fees
Sep 30 - Oct 1
Family Stays: Middletown, CT
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

2. #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 ￥33,272
￥64,515 total
includes taxes & fees
Sep 20 - Sep 21
#24 Serenity A Lakefront Cottage Retreat
A two-story house with a front porch, a garage, and a well-maintained lawn.

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
9.6 out of 10, Exceptional, (18 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 ￥78,474
￥136,850 total
includes taxes & fees
Sep 15 - Sep 16
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

4. 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 ￥18,439
￥45,581 total
includes taxes & fees
Sep 7 - Sep 8
Once the old Schools house now a newly furnished Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

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 ￥18,439
￥45,581 total
includes taxes & fees
Sep 20 - Sep 21
Newly Remodeled 1-BR Close to Everything yet Very Private
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is ￥42,190
￥100,045 total
includes taxes & fees
Sep 8 - Sep 9
The Cottage by the Woods -private getaway to relax
A modern kitchen with a central island, bar stools, and pendant lighting.

7. 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 ￥101,569
￥161,573 total
includes taxes & fees
Sep 7 - Sep 8
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

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

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is ￥26,017
￥78,048 total
includes taxes & fees
Sep 8 - Sep 9
Cozy basement apartment with private bathroom, kitchen and entrance.
A modern living room with a grey sectional sofa, a wooden dining table, and a kitchen in the background.

9. #22- 4 Br 2 Ba house-Central CT

#22- 4 Br 2 Ba house-Central CT
New Britain
10.0 out of 10, Exceptional, (1 review)
"Host was great and responsive and the property was perfect for what we needed."
United States
Hilda C.
The price is ￥29,928
￥64,732 total
includes taxes & fees
Sep 7 - Sep 8
#22- 4 Br 2 Ba house-Central CT
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

10. 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, (29 reviews)
"Was a great stay"
United States
John S.
The price is ￥23,283
￥48,183 total
includes taxes & fees
Sep 7 - Sep 8
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A modern living room with a sofa, a coffee table, and a rug.

11. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (9 reviews)
"Good location"
United States
Arthur
The price is ￥13,923
￥19,137 total
includes taxes & fees
Sep 8 - Sep 9
Entire guest suite in South Windsor, Connecticut

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 ￥41,178
￥80,468 total
includes taxes & fees
Sep 14 - Sep 15
Prime West Hartford Center: Timeless Charm

13. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is ￥46,648
￥94,898 total
includes taxes & fees
Sep 7 - Sep 8
#41- Available 12/8! - sleeps 14
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

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 ￥20,158
￥45,683 total
includes taxes & fees
Sep 28 - Sep 29
Modern & Cozy Cape | 4 Bedroom House | Central Location
A modern dining area with a marble table, white chairs, and a chandelier.

15. 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 ￥25,783
￥52,933 total
includes taxes & fees
Sep 10 - Sep 11
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

16. #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 ￥33,272
￥73,890 total
includes taxes & fees
Oct 5 - Oct 6
#27- Luxury Collection
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

17. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥27,494
￥75,706 total
includes taxes & fees
Sep 9 - Sep 10
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful views of the water and grounds. Everything was well maintained and clean."
Nina 2-night trip
Posted less than an hour ago
Water's Edge Resort & Spa

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
197
Accommodation
341 Vacation Homes
Lowest Price
￥19,137
Highest Price
￥161,573