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. 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

2. 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.
$766 nightly
The price is $866
Aug 11 - Aug 12
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Exterior

3. 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 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

4. 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.
$196 nightly
The price is $222
Sep 7 - Sep 8
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
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!
Interior

6. 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 11 - Aug 12
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

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

10/10 Excellent
"The room was nice and large and the kitchen area was perfect for our needs. Home 2 Suites is our go to hotel for out trips!"
Alexander 3-night trip
Posted 10 hours ago
Home2 Suites by Hilton East Haven New Haven

Find out more about Middletown

Middletown Cottages information

Number of reviews
235
Accommodation
108 Cottages
Lowest Price
$222
Highest Price
$866

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.
How can I find cheap cottages in Middletown?
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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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