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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Compare 34 Cottages in Middletown with updated reviews, rates, and availability.

Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!
Charming Connecticut Retreat Near Museums & Hiking
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, cookware/dishes/utensils

Charming Connecticut Retreat Near Museums & Hiking

3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Guilford Carriage House at Granite Lodge!
Interior

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
Pet-friendly Lebanon House w/ Lake Access!
Interior

Pet-friendly Lebanon House w/ Lake Access!

3.0 star property
Pet-friendly Lebanon House w/ Lake Access!
Cozy Westbrook Vacation Rental - Walk to Beach!
Property grounds

Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Elegant Middlefield Getaway w/ Game Room!
Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Lakefront Home, Close to Mt Southington!
House (3 Bedrooms) | Interior

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
Upscale Waterbury Retreat w/ Indoor Hot Tub!
House (3 Bedrooms) | Interior

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Modern Terryville Cottage w/ Deck & Lake View!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Wolcott Home w/ Deck: Near Connecticut Attractions
Interior

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
Historic Essex Home w/ Large Yard Near Downtown!
TV

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
Historic Essex Home w/ Large Yard Near Downtown!
Westbrook Home w/ Ocean Views - Walk to Beach
Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Waterfront Cottage w/ Sunroom + Patio & Grill
Interior

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Charming Old Saybrook Home: Half-mi to Sand & Sea!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Old Saybrook Home: Half-mi to Sand & Sea!

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Charming Westbrook Cottage, Steps to Private Beach
Interior

Charming Westbrook Cottage, Steps to Private Beach

3.0 star property
Charming Westbrook Cottage, Steps to Private Beach
Charming Farmington Home ~ 5 Mi to Uconn Health!
Interior

Charming Farmington Home ~ 5 Mi to Uconn Health!

3.0 star property
Charming Farmington Home ~ 5 Mi to Uconn Health!
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Interior

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3.0 star property
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
11 Mi to Powder Ridge Mountain: Connecticut Home
Interior

11 Mi to Powder Ridge Mountain: Connecticut Home

3.0 star property
11 Mi to Powder Ridge Mountain: Connecticut Home
Dreamy Waterfront Westbrook Home on Private Beach
Interior

Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
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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Other property types in Middletown

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is NT$4,482
NT$5,154 total
includes taxes & fees
Apr 29 - Apr 30
Postcard Cabins Machimoodus
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.

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.