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

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Middletown cottages

Exterior

1. 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.
$275 nightly
The price is $312
Sep 3 - Sep 4
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
House (3 Bedrooms) | Interior

2. 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
Lakefront Home, Close to Mt Southington!
Exterior

3. Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
9.8 out of 10, Exceptional, (159 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

4. 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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$288 nightly
The price is $326
Sep 2 - Sep 3
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

5. 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
$322 nightly
The price is $364
Aug 24 - Aug 25
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
$216 nightly
The price is $245
Sep 2 - Sep 3
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
$309 nightly
The price is $350
Aug 24 - Aug 25
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Very clean room, some hidden costs added during check in. Resort fee tax and town or state"
Jan 1-night trip
Posted less than an hour ago
Water's Edge Resort & Spa

Find out more about Middletown

Middletown Cottages information

Number of reviews
256
Accommodation
108 Cottages
Lowest Price
$245
Highest Price
$388

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.
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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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