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

Search Middletown Cottages

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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.
$286 nightly
The price is $324
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
Exterior

2. 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)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$291 nightly
The price is $329
Sep 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
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
10.0 out of 10, Exceptional, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$324 nightly
The price is $366
Sep 3 - Sep 4
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

4. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
$203 nightly
The price is $229
Sep 8 - Sep 9
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Dining

5. 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)
"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 31 - Sep 1
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
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. 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.
$705 nightly
The price is $797
Aug 31 - Sep 1
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Clean"
Barbara 2-night trip
Posted 2 hours ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

Find out more about Middletown

Middletown Cottages information

Number of reviews
50
Accommodation
105 Cottages
Lowest Price
$229
Highest Price
$797

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?
Expedia is here to help you locate cheap cottages in Middletown. To reserve a fantastic stay in a matter of clicks, simply use our handy filter tool to refine your search by budget, amenities and star rating.
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.

Explore a world of travel with Expedia