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

Search Middletown Cottages

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Middletown cottages

Exterior

Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (18 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$297 nightly
The price is $337
Aug 19 - Aug 20
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
House (3 Bedrooms) | Interior

Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
$410 nightly
The price is $472
Aug 3 - Aug 4
Total with taxes and fees
Lakefront Home, Close to Mt Southington!
Exterior

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
9.8 out of 10, Exceptional, (158 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
$343 nightly
The price is $388
Aug 20 - Aug 21
Total with taxes and fees
Go Jump in the Lake!
Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay"
United States
JM B.
$217 nightly
The price is $246
Jul 29 - Jul 30
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

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
$319 nightly
The price is $361
Aug 2 - Aug 3
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Interior

Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
$287 nightly
The price is $324
Jul 29 - Jul 30
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
House (3 Bedrooms) | 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
$469 nightly
The price is $539
Jul 31 - Aug 1
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

8/10 Good
"It shows they have a pool and they don’t."
Ava 1-night trip
Posted less than an hour ago
Courtyard by Marriott Waterbury Downtown

Find out more about Middletown

Middletown Cottages information

Number of reviews
229
Accommodation
108 Cottages
Lowest Price
$246
Highest Price
$539

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.
How can I find cheap cottages in Middletown?
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.

Explore a world of travel with Expedia