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

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Check prices for these dates

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

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, (63 reviews)
"We enjoyed our stay"
United States
JM B.
$183 nightly
The price is $207
Oct 21 - Oct 22
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, (30 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$257 nightly
The price is $291
Oct 20 - Oct 21
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, a mailbox, and a lawn.

3. 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.
$312 nightly
The price is $354
Oct 27 - Oct 28
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A compact kitchen with white cabinets, a microwave, an oven, a refrigerator, and a trash bin.

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
$287 nightly
The price is $324
Oct 20 - Oct 21
Total with taxes and fees
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
$469 nightly
The price is $539
Oct 20 - Oct 21
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A two-story house with a porch, multiple windows, and a front door.

6. 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)
"Very clean and comfortable"
United States
Francine F.
$485 nightly
The price is $549
Oct 20 - Oct 21
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A wooden deck with two Adirondack chairs and a sliding glass door leading to a room.

7. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
$520 nightly
The price is $588
Oct 27 - Oct 28
Total with taxes and fees
Waterfront Lake Cottage - Lake Access -Kayaks
A room with white shelving units filled with framed photos and decorative items, a window with blinds, and a radiator.

8. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
$303 nightly
The price is $343
Oct 20 - Oct 21
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

8/10 Good
"Need more clear update everything"
benjamin 1-night trip
Posted less than an hour ago
Hamden Hotel and Suites – Hamden New Haven

Find out more about Middletown

Middletown Cottages information

Number of reviews
108
Accommodation
104 Cottages
Lowest Price
$207
Highest Price
$588

Frequently asked questions

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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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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.

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