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

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$290 nightly
The price is $328
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
Exterior

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
$197 nightly
The price is $222
Sep 15 - Sep 16
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

3. 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
$324 nightly
The price is $366
Aug 24 - Aug 25
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Dining

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
6.0 out of 10, (1 review)
"Host was communicative before booking, but communication was not possible other than solely thru this platform. It was difficult to advise the host of my experience or needs. The bedroom rug had a potent urine odor, as well as, being dirty. The toilet was not clean. There is no dishwasher, limited wine glasses and one coffee mug. Though this is a pet-friendly host, the rooms smelled of pet urine. The window A/Cs were not adequately sealed, allowing bugs, moths, and spiders inside the bedroom and...
United States
Liz H.
$287 nightly
The price is $324
Aug 23 - Aug 24
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
House (3 Bedrooms) | Interior

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

6. 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.
$781 nightly
The price is $885
Aug 23 - Aug 24
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
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
"It was a nice experience the staff was very helpful"
Rosa 1-night trip
Posted 4 hours ago
New Haven Hotel

Find out more about Middletown

Middletown Cottages information

Number of reviews
20
Accommodation
105 Cottages
Lowest Price
$222
Highest Price
$885

Frequently asked questions

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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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