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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middletown cottages

A white cottage with a front door, a garage, and a small porch with a potted plant.

1. 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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$271 nightly
The price is $309
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, 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$297 nightly
The price is $338
Sep 28 - Sep 29
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay"
United States
JM B.
$203 nightly
The price is $230
Oct 6 - Oct 7
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
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
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 17 - Sep 18
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
Sep 17 - Sep 18
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A coastal residential area with houses, a beach, and a pier.

6. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
$872 nightly
The price is $993
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.
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Top Middletown Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Very nice hotel right in the heart of New Haven and a very reasonable distance from the train station. I would stay here again if I'm back in town."
Douglas 1-night trip
Posted 5 hours ago
New Haven Hotel

Find out more about Middletown

Middletown Cottages information

Number of reviews
127
Accommodation
105 Cottages
Lowest Price
$230
Highest Price
$993

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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