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

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middletown cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
$206 nightly
The price is $235
Nov 12 - Nov 13
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A two-story house with a porch, a mailbox, and a lawn.

2. 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
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
$252 nightly
The price is $287
Nov 15 - Nov 16
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A white cottage with a front door, a garage, and a small porch with a potted plant.

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, (32 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$300 nightly
The price is $341
Nov 12 - Nov 13
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
$273 nightly
The price is $310
Nov 12 - Nov 13
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

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
Nov 12 - Nov 13
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Two Adirondack chairs facing a river with a grassy area and trees in the background.

6. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
10.0 out of 10, Exceptional, (1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
United States
Victoria F.
$512 nightly
The price is $583
Dec 8 - Dec 9
Total with taxes and fees
Waterfront Lake Cottage - Lake Access -Kayaks
A lakeside house with a deck, surrounded by trees and a dock.

7. Waterfront! Brand New Cozy Cottage in Old Lyme, CT

Waterfront! Brand New Cozy Cottage in Old Lyme, CT
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Was a great stay very cute property and quiet neighborhood. Stores nearby and easy to access. Friendly and helpful host."
United States
Jessica H.
$403 nightly
The price is $459
Nov 20 - Nov 21
Total with taxes and fees
Waterfront! Brand New Cozy Cottage in Old Lyme, CT
A two-story house with a porch, multiple windows, and a front door.

8. 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)
"Very clean and comfortable"
United States
Francine F.
$497 nightly
The price is $566
Nov 12 - Nov 13
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

9. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
$353 nightly
The price is $403
Dec 2 - Dec 3
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
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

Economy Inn

Economy Inn

8/10 Good
"I am not sure but it seems like this hotel has new management. If not, then the old owners finally gave the place a makeover."
Joseph 1-night trip
Posted 15 hours ago
Economy Inn

Find out more about Middletown

Middletown Cottages information

Number of reviews
120
Accommodation
104 Cottages
Lowest Price
$235
Highest Price
$583

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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