Middletown Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Middletown holiday rentals

Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (23 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$901
HK$1,758 total
includes taxes & fees
15 Apr - 16 Apr
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
6.0 out of 10, (2 reviews)
"The apartment was exactly what we needed to rest between events at Wesleyan. Good communication, fixed an air conditioner and added one prior to our arrival (and it was very very hot. So it was appreciated."
United States
Carolyn O.
The price is HK$909
HK$2,339 total
includes taxes & fees
6 Apr - 7 Apr
Private Apt in Middletown-Wesleyan 101
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is HK$776
HK$2,193 total
includes taxes & fees
4 Apr - 5 Apr
2BR Apartment Near Wesleyan 301
Smart TV

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Nice place"
United States
Jousette C.
The price is HK$1,724
HK$2,202 total
includes taxes & fees
15 Apr - 16 Apr
3-bedroom Unit in tranquil Middletown
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is HK$972
HK$2,450 total
includes taxes & fees
8 Apr - 9 Apr
3 BR Apartment Near Wesleyan 201
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is HK$1,011
HK$2,495 total
includes taxes & fees
14 Apr - 15 Apr
2BR Apartment Near Wesleyan 102
Dining

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
The price is HK$1,136
HK$2,957 total
includes taxes & fees
6 Apr - 7 Apr
3 BR Apartment Near Wesleyan 202
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (132 reviews)
"Our favorite place to visit ♥️"
United States
Teresa
The price is HK$1,011
HK$1,523 total
includes taxes & fees
15 Apr - 16 Apr
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (35 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is HK$745
HK$1,464 total
includes taxes & fees
14 Apr - 15 Apr
Walk To Goodspeed Opera House!
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 HK$1,325
HK$2,487 total
includes taxes & fees
6 Apr - 7 Apr
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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)
"Check in easy, great communications - very quick & answered any questions. Great location for what we needed, layout of house was perfect for us, Roku let us stream all the shows we wanted to watch. Ate out so didn’t use kitchen a lot, beds were comfortable. When we come back to visit our daughter will use again. "
United States
mike p.
The price is HK$1,250
HK$2,598 total
includes taxes & fees
5 Apr - 6 Apr
15mins to Hartford, Home in Manchester w/ King Bed
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 HK$939
HK$3,488 total
includes taxes & fees
8 Apr - 9 Apr
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is HK$676
HK$1,655 total
includes taxes & fees
6 Apr - 7 Apr
Crested One Place - with Free Parking, Heat & AC
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (14 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveller
The price is HK$745
HK$2,073 total
includes taxes & fees
5 Apr - 6 Apr
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$941
HK$1,238 total
includes taxes & fees
5 Apr - 6 Apr
Humble Abode #2
Exterior

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is HK$1,677
HK$3,694 total
includes taxes & fees
14 Apr - 15 Apr
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$1,724
HK$3,995 total
includes taxes & fees
6 Apr - 7 Apr
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior

Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds

Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds
East Rock
9.6 out of 10, Exceptional, (8 reviews)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
United States
Derek L.
The price is HK$1,677
HK$3,694 total
includes taxes & fees
6 Apr - 7 Apr
Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds
TV, offices

PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds

PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"The house was super clean and perfect for a larger group. Also, the location was convenient to nearby attractions."
United States
Luke B.
The price is HK$1,677
HK$3,694 total
includes taxes & fees
7 Apr - 8 Apr
PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is HK$2,116
HK$3,703 total
includes taxes & fees
6 Apr - 7 Apr
Welcoming 4-bedroom house in charming Hamden
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

8/10 Good
"Clean room, friendly staff, and easy parking. Only note would be that tubs shouldn’t be included in the picture if they’re not included with the room."
Anisa 1-night trip
Posted 5 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Are there holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Kidcity Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Large Charming Historic House close to Beaches: This holiday home rental outside of Middletown is located near the beach, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middletown?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Kidcity Children's Museum and Van Vleck Observatory, whereas Connecticut River and Middletown Nature Gardens are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Artfarm.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.