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

Search Middletown Cottages

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Middletown cottages

Exterior

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.
$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
Exterior

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, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$309 nightly
The price is $350
Sep 28 - Sep 29
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

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.
$205 nightly
The price is $232
Oct 6 - Oct 7
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Private kitchen

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 14 - Sep 15
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
Exterior

5. 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.
$477 nightly
The price is $539
Sep 14 - Sep 15
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
House (3 Bedrooms) | Interior

6. 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 14 - Sep 15
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior

7. 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.
$965 nightly
The price is $1,096
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"Amazing pool. Lived the river trails and breakfast"
Christine 2-night trip
Posted 17 hours ago
Hampton Inn & Suites Hartford/East Hartford

Find out more about Middletown

Middletown Cottages information

Number of reviews
134
Accommodation
105 Cottages
Lowest Price
$232
Highest Price
$1,096

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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