Search Middletown Cottage Rentals from CA $185

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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)
"We enjoyed our stay"
United States
JM B.
The price is CA $185
CA $318 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $208
CA $404 total
includes taxes & fees
Nov 9 - Nov 10
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, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $284
CA $481 total
includes taxes & fees
Nov 8 - Nov 9
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
The price is CA $246
CA $416 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is CA $383
CA $756 total
includes taxes & fees
Nov 8 - Nov 9
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.
The price is CA $445
CA $796 total
includes taxes & fees
Nov 8 - Nov 9
Waterfront Lake Cottage - Lake Access -Kayaks
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

7. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is CA $394
CA $531 total
includes taxes & fees
Nov 17 - Nov 18
Westbrook Getaway-Near Beaches, Train & Shoreline
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.
The price is CA $342
CA $766 total
includes taxes & fees
Nov 8 - Nov 9
Adorable Cottage with Cottage porch, walk to water & town
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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Learn more about Middletown

Wesleyan University's stunning campus and the Connecticut River waterfront offer perfect spots for afternoon strolls and picnics. Explore Main Street's indie bookshops and farm-to-table restaurants, then catch a show at the historic Oddfellows Playhouse where locals gather.

See all hotels in Middletown
A coastal cityscape with a marina, dense urban buildings, and a river.

Top reviews in Middletown

A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.
Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell
Cromwell

10/10 Excellent

Solid
Canada
Chris
Reviewed April 7, 2026
Springhill Suites by Marriott Hartford Cromwell

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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