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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 88 Cottages in Middletown with updated reviews, rates, and availability.

Waterfront Cottage in Branford
Exterior

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (90)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford
Historic Whitneyville Cottage
Exterior detail

Historic Whitneyville Cottage

9.6 out of 10, Exceptional, (14)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is AED 793
AED 1,850 total
includes taxes & fees
24 Feb - 25 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
The Dream Location for Your Perfect Vacation
Property grounds

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
Go Jump in the Lake!

Go Jump in the Lake!

10.0 out of 10, Exceptional, (138)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Fall sunsets are a prize possession here at the lake!

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (29)
"Vladimir and Cristina's Plymouth listing is such a great find! It was a great home base for visiting family in the area for the holidays. I don't think I've ever been to a rental that had everything you could possibly need. All this plus an amazing view - we'll be back!"
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Updated cottage "Beriozka" on Cedar Lake
Exterior

Updated cottage "Beriozka" on Cedar Lake

10.0 out of 10, Exceptional, (5)
"Pleasant and fully equipped, walking distance to a small lake with a beach good for watching the sunrise and reading."
Updated cottage "Beriozka" on Cedar Lake
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Exterior

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
Living area

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Exterior

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AED 353
AED 648 total
includes taxes & fees
26 Feb - 27 Feb
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Living area

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Welcome to our cute getaway

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"We had a magical Christmas here. I fulfilled a lifelong dream to host my family for Christmas Eve Smorgasbord and the jigsaw puzzle had all of the pieces! "
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Enchanted Waterfront Cottage
Beach

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Charming Westbrook Cottage, Steps to Private Beach
Westbrook Vacation Rental | 3BR | 1BA | 800 Sq Ft | Steps Required

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
DIRECT WATERFRONT PRIVATE BEACH
Exterior

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
Guilford Carriage House at Granite Lodge!
Guilford Vacation Rental | 1BR | 1BA | Step-Free Access via Side Door

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (9)
"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!
Relax with a beautiful lake view
Perfect view of the lake from your private deck

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Exterior

Charming 3-bedroom cottage in Old Saybrook with AC, WiFi

Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Family Friendly Waterfront Cottage
Outdoor dining

Family Friendly Waterfront Cottage

4.0 out of 10, (1)
"This property is completely misrepresented! I sent pictures in an email to someone named Luis two days ago. 1. Home is on a gravel road and you need to walk down a steep hill to get to the house. 2. House is covered in cob webs inside and out and windows are dirty and covered in green mold. 3. Two queen beds listed turned out to be full size mattresses (we measured!) so that my husband and I had to sleep in separate rooms. 4. Third bedroom had a sleeper sofa that we had to use to keep an...
Family Friendly Waterfront Cottage
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, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
Postcard Cabins Machimoodus
Waterfront House with picture-perfect views from all 3 levels.
Third level patio, off of bedroom with queen bed and twin bed with trundle.

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
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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