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

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Middletown cottages

Exterior

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (18 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$295 nightly
The price is $334
Aug 19 - Aug 20
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Exterior

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
9.8 out of 10, Exceptional, (158 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
Jul 26 - Jul 27
Total with taxes and fees
Go Jump in the Lake!
House (3 Bedrooms) | Interior

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
$410 nightly
The price is $472
Aug 3 - Aug 4
Total with taxes and fees
Lakefront Home, Close to Mt Southington!
Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay"
United States
JM B.
$217 nightly
The price is $246
Aug 12 - Aug 13
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

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
$319 nightly
The price is $361
Jul 26 - Jul 27
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Interior

Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
$287 nightly
The price is $324
Jul 26 - Jul 27
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
Exterior

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

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
House (3 Bedrooms) | Interior

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
Jul 31 - Aug 1
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Breakfast was great, view was super pretty, great value for the price"
Olivia 1-night trip
Posted 5 hours ago
The Capitol Hotel

Find out more about Middletown

Middletown Cottages information

Number of reviews
237
Accommodation
108 Cottages
Lowest Price
$246
Highest Price
$539

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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