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

Search Middletown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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.
$278 nightly
The price is $315
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
Exterior

2. 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

3. 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.
$199 nightly
The price is $225
Sep 8 - Sep 9
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
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, (26 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$292 nightly
The price is $330
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
$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!
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
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.
$312 nightly
The price is $353
Sep 1 - Sep 2
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
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.
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

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"Very clean rooms and pleasant staff!!"
Marilyn 5-night trip
Posted 4 hours ago
Motel 6 New Haven - Branford, CT

Find out more about Middletown

Middletown Cottages information

Number of reviews
10,060
Accommodation
108 Cottages
Lowest Price
$81
Highest Price
$267

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