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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Middletown cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (61 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €192
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A two-story house with a porch, a mailbox, and a lawn.

2. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is €322
includes taxes & fees
20 Oct - 21 Oct
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A white cottage with a front door, a garage, and a small porch with a potted plant.

3. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is €274
includes taxes & fees
18 Oct - 19 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

4. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
The price is €291
includes taxes & fees
14 Oct - 15 Oct
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

5. 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 €481
includes taxes & fees
14 Oct - 15 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A living room with a sofa, armchair, coffee table, and a television.

6. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is €251
includes taxes & fees
11 Nov - 12 Nov
Westbrook Getaway-Near Beaches, Train & Shoreline
A house with a porch and a small shed in the background.

7. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
The price is €534
includes taxes & fees
27 Oct - 28 Oct
Waterfront Lake Cottage - Lake Access -Kayaks
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"A fairly clean hotel with very nice staff! The only thing that bothered us was the constant smell of weed/marijuana every day we were there."
Denise 3-night trip
Posted 2 hours ago
Holiday Inn Express Southington by IHG

Find out more about Middletown

Middletown Cottages information

Number of reviews
36
Accommodation
103 Cottages
Lowest Price
€192
Highest Price
€534

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think that vacays should be stress-free, so if you're seeking cottages in Middletown at a nice price, Expedia can help. Keep the budget under control and opt for a thrifty option surrounded by nature, or splurge on an upmarket cottage to spoil your loved ones.
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Expedia is here to help you locate cheap cottages in Middletown. To reserve a fantastic stay in a matter of clicks, simply use our handy filter tool to refine your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
After you've settled into your hotel, set out and explore the incredible things Middletown has on offer. Kidcity Children's Museum is a great attraction to add to your itinerary.