Bright colors of autumn. View above. Road in the forest. Middletown, Connecticut

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Middletown vacation rentals

Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is AED 632
AED 1,380 total
includes taxes & fees
29 Jun - 30 Jun
3 BR Apartment Near Wesleyan 201
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 AED 1,057
AED 1,877 total
includes taxes & fees
22 Jul - 23 Jul
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (28 reviews)
"House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!"
United States
Diana C.
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.4 out of 10, Good, (3 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AED 588
AED 1,322 total
includes taxes & fees
1 Jul - 2 Jul
Private Apt in Middletown-Wesleyan 101
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (159 reviews)
"Great stay! "
United States
Tanitra
The price is AED 621
AED 883 total
includes taxes & fees
15 Jul - 16 Jul
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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, (27 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is AED 2,388
AED 3,798 total
includes taxes & fees
28 Jun - 29 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Marina

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
The price is AED 2,094
AED 3,337 total
includes taxes & fees
1 Jul - 2 Jul
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
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.
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Property grounds

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 900
AED 1,156 total
includes taxes & fees
30 Jun - 1 Jul
NEW Coastal Cottage 2 Miles to Beach + Lake Access
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 569
AED 1,013 total
includes taxes & fees
1 Jul - 2 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Terrace/patio

Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (30 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
The price is AED 1,230
AED 2,233 total
includes taxes & fees
2 Jul - 3 Jul
Charming New England Home in West Hartford Center
Exterior

Spacious Urban Townhouse • Groups and Family

Spacious Urban Townhouse • Groups and Family
Clay-Arsenal
10.0 out of 10, Exceptional, (1 review)
"Excellent communication with the host. Very clean and comfortable property. We really enjoyed our stay."
United States
Kathy D.
Spacious Urban Townhouse • Groups and Family
Dining

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (38 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is AED 4,408
AED 6,641 total
includes taxes & fees
7 Jul - 8 Jul
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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, (66 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,927 total
includes taxes & fees
29 Jun - 30 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 1,350
AED 2,930 total
includes taxes & fees
1 Jul - 2 Jul
Beachside Bliss w/ Game Room, Gym & Golf Green
TV, fireplace

#41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AED 1,057
AED 2,174 total
includes taxes & fees
28 Jun - 29 Jun
#41- Available 12/8! - sleeps 14
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 AED 2,122
AED 2,870 total
includes taxes & fees
30 Jun - 1 Jul
Heavenly Home in New Haven /5 mins drive from Yale
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is AED 612
AED 1,835 total
includes taxes & fees
29 Jun - 30 Jun
Cozy basement apartment with private bathroom, kitchen and entrance.
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, (8 reviews)
"We had a very nice stay at Roger’s Lake! The house was so cool! It had all the amenities we needed and the location was charming and peaceful. In particular, the beds are really comfortable! They have this awesome exercise room where you can stretch out and enjoy the light. The host, Peter, was especially easy to work with and was very communicative. My family and I are hoping to come back soon for another stay."
United States
Andrea
The price is AED 592
AED 1,830 total
includes taxes & fees
28 Jun - 29 Jun
Rogers Lake House (87) · CT College+Beach+USCGA
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is AED 704
AED 1,323 total
includes taxes & fees
7 Jul - 8 Jul
1 Min to I-91 - Newly Renovated Modern 2 BR Home
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

Frequently asked questions

Are there vacation rentals in Middletown?

Yes, you can find vacation rentals in Middletown close to Van Vleck Observatory, or you can choose a more remote option if you want 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 vacation rentals that Middletown has to offer?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This vacation home rental outside of Middletown is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

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

What’s there to see and do in Middletown?

Family-friendly attractions include Van Vleck Observatory and Kidcity Children's Museum, whereas Wadsworth Falls State Park and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and General Mansfield House.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Middletown. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.