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

Search Middletown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (60 reviews)
"We enjoyed our stay"
United States
JM B.
$207 nightly
The price is $234
Oct 20 - Oct 21
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A white cottage with a front door, a garage, and a small porch with a potted plant.

2. 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, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$263 nightly
The price is $297
Oct 7 - Oct 8
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, multiple windows, and a front door.

3. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Great host and property"
United States
Kevin K.
$442 nightly
The price is $503
Sep 27 - Sep 28
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A two-story house with a porch, a mailbox, and a lawn.

4. 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$306 nightly
The price is $346
Oct 6 - Oct 7
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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
$469 nightly
The price is $539
Sep 26 - Sep 27
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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.

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
8.0 out of 10, Very good, (2 reviews)
"We enjoyed our stay at the cottage. It was perfect for traveling with our dogs very comfortable, nice and quiet."
United States
Ed B.
$287 nightly
The price is $324
Sep 27 - Sep 28
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A coastal residential area with houses, a beach, and a pier.

7. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Unbeatable views and professional hosts."
United States
Russell A.
$991 nightly
The price is $1,122
Sep 28 - Sep 29
Total with taxes and fees
Direct waterfront renovated cottage.
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"The person checking us in was very pleasant and helpful. The rooms were clean and well kept, noise level was low and not disturbing. Price was very reasonable."
Steven 1-night trip
Posted 7 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Middletown

Middletown Cottages information

Number of reviews
196
Accommodation
105 Cottages
Lowest Price
$234
Highest Price
$1,122

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