Photo by Simmie Reagor

Search Cottages in Middletown

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 85 Cottages in Middletown with updated reviews, rates, and availability.

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beach Bungalow, large porch, 1/2 mile to the water.
8.4 out of 10, Very Good, (5)
"Very nice and comfortable property "
The price is AED 848
AED 1,556 total
includes taxes & fees
30 Nov - 1 Dec
Beach Bungalow, large porch, 1/2 mile to the water.
Charming Deep River Vacation Rental on Star Lake!
7.0 out of 10, Good, (4)
"Nice relaxing small house for a quick weekend getaway. Plenty of space in the kitchen and bedrooms. The shower is very very small, especially with a curtain that you kind of have to hold back away from you while you shower. If you like very firm beds youre in luck, the matresses are pretty firm. I would bring your own pillows as those provided were very thin. Other than that, its the perfect spot for a getaway. We had a wonderful relaxing weekend."
Charming Deep River Vacation Rental on Star Lake!
Shalom Cottage with private beach rights.
9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 301
AED 610 total
includes taxes & fees
17 Nov - 18 Nov
Shalom Cottage with private beach rights.
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Enchanted Waterfront Cottage
9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (20)
"The island was the perfect vacation spot for a large family group! We enjoyed the paddle boards and kayaks daily , exploring the ocean and other Thimnle Islamds. We swam off the private beach when the rose was right and off the dock. The gazebo, porches and seating on the rocks were great for reading and boat and bird watching. The single storm was even a unique experience - weather and ocean on all sides! The ferry was convenient - making of island meals possible. E"
Private Island Compound with Large Cottage and Guest House
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (8)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!
Waterfront Cottage w/ Sunroom + Patio & Grill
8.0 out of 10, Very Good, (5)
"Overall it was a nice relaxing stay. Nice and clean. Lots of sun through the back windows. Amenities were much appreciated, in kitchen, bathroom and bedrooms."
Waterfront Cottage w/ Sunroom + Patio & Grill
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (12)
"Very convenient for what we needed. Nice little cottage."
Historic Whitneyville Cottage
Go Jump in the Lake!
10.0 out of 10, Exceptional, (137)
"We like this place a lot. House was clean and Todd was very responsive to my questions. There are two bedrooms with one on the second floor. One thing we didn’t realize was, to get to the second floor there is a spiral staircase. "
Go Jump in the Lake!
DIRECT WATERFRONT PRIVATE BEACH
9.4 out of 10, Exceptional, (23)
"I picked this rental because I recognized it as soon as I saw it! I grew up 5 houses from here. The rental was immaculate, the beach beautiful….home. Owners were very nice and helpful. They say you can’t go home again but I got pretty close! Fantastic spot. I’ll be back!"
DIRECT WATERFRONT PRIVATE BEACH
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (60)
"Our 2nd time to stay at this cozy little cottage. We always enjoy our time spent here. And we do enjoy the homemade banana bread."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
The Perfect Family Beachfront Cottage The Viola Cottage
10.0 out of 10, Exceptional, (34)
"A fantastic visit! The cottage was so cute, quiet and right on the beach. Karl was an excellent host and so easy to work with. We will most definitely be back!!"
The Perfect Family Beachfront Cottage The Viola Cottage
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (12)
"Property is charming, beautifully decorated, clean. Host was very responsiveand even shared produce from her lovely garden! We hope to return."
The gardners Cottage 1 mile from long Island Sound - pet friendly
'Grandma's Cottage' w/ Sunroom: Walk to Beach
8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to 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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middletown

Cozy newly remodeled home close to major amenities in Connecticut a
8.4 out of 10, Very Good, (16)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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?
Booking a cottage in Middletown is as simple as clicking on your travel dates and choosing your ideal place for a vacation in nature. From chic retreats to low-cost properties and cottages that come with amenities like laundry facilities, Expedia has something for all styles and tastes. As for the best deals around? We have them too!
How can I find cheap cottages in Middletown?
The best way to track down cheap cottages in Middletown is with Expedia’s useful filter tool. Narrow down your search by budget, star rating and amenities to grab awesome rates in just a few clicks.