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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Middletown vacation homes

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is ￥30,776
￥61,341 total
includes taxes & fees
May 18 - May 19
#24 *Serenity* A Lakefront Cottage Retreat
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 ￥32,740
￥72,665 total
includes taxes & fees
May 11 - May 12
#29 - Modern 5 Bedroom/2 Bath
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is ￥25,205
￥78,355 total
includes taxes & fees
May 12 - May 13
Rogers Lake House (87) · CT College+Beach+USCGA
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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,446
￥46,068 total
includes taxes & fees
May 12 - May 13
Once the old Schools house now a newly furnished Apartment
Smart TV

15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed
Manchester
9.2 out of 10, Wonderful, (7 reviews)
"Great location, spacious, comfortable and clean. The host was very responsive and easy to work with, Definitely deserves 5 stars for quality and price."
Singapore
Angelo N.
The price is ￥23,595
￥50,319 total
includes taxes & fees
May 13 - May 14
15mins to Hartford, Home in Manchester w/ King Bed
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is ￥31,264
￥55,806 total
includes taxes & fees
May 12 - May 13
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior

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, (10 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥30,692
￥76,912 total
includes taxes & fees
Jun 1 - Jun 2
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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, (9 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is ￥22,869
￥49,484 total
includes taxes & fees
May 27 - May 28
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"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 ￥13,627
￥18,825 total
includes taxes & fees
May 10 - May 11
Entire guest suite in South Windsor, Connecticut
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (2 reviews)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is ￥47,130
￥80,149 total
includes taxes & fees
May 12 - May 13
Welcoming 4-bedroom house in charming Hamden
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (22 reviews)
"Great place"
United States
John S.
The price is ￥24,230
￥51,000 total
includes taxes & fees
May 12 - May 13
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥48,772
￥82,170 total
includes taxes & fees
May 12 - May 13
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is ￥21,885
￥40,331 total
includes taxes & fees
May 12 - May 13
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fridge, microwave, oven, stovetop

#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, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is ￥45,397
￥89,112 total
includes taxes & fees
May 13 - May 14
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is ￥94,506
￥126,504 total
includes taxes & fees
May 31 - Jun 1
Heavenly Home in New Haven /5 mins drive from Yale
Fridge, microwave, oven, stovetop

#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 ￥33,285
￥73,450 total
includes taxes & fees
May 19 - May 20
#27- Luxury Collection
Interior

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 ￥15,614
￥21,111 total
includes taxes & fees
May 10 - May 11
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.4 out of 10, Exceptional, (21 reviews)
"Great value very close to university. "
United States
Lawrence
The price is ￥19,696
￥35,054 total
includes taxes & fees
May 12 - May 13
Stocked home close to Yale, in Heart of New Haven
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, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is ￥93,792
￥149,520 total
includes taxes & fees
May 20 - May 21
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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

The Capitol Hotel

The Capitol Hotel

4/10 Poor
"When I pulled up I was greeted by an enormius rat running across the lot. The lobby reeked of a oke.. Both ciggies and weed. Hallways as well. Room was smoke free and comfy but noisy af with amtrack station next door."
Stephanie 2-night trip
Posted 5 hours ago
The Capitol Hotel

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
261
Accommodation
357 Vacation Homes
Lowest Price
￥18,825
Highest Price
￥149,520