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In two weeks
Oct 3 - Oct 5
In one month
Oct 17 - Oct 19
In two months
Nov 14 - Nov 16
In three months
Dec 12 - Dec 14

Cottages in Middletown

Direct waterfront renovated cottage.
Exterior

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (80)
"Beautiful location on water, comfortable cottage "
$1,177 nightly
The price is $1,332
Sep 20 - Sep 21
Total with taxes and fees
Direct waterfront renovated cottage.
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
$193 nightly
The price is $218
Oct 7 - Oct 8
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Go Jump in the Lake!
Exterior

Go Jump in the Lake!

10.0 out of 10, Exceptional, (144)
"owner was super nice and the environment was great i would come back "
Go Jump in the Lake!
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (81)
"This was a great property and close to many things to see and visit. The welcome note and goodies were much appreciated. Great communication from the host!!!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
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, (17)
"Robin was an excellent host and the cottage was beautiful and very well kept! After a very long work day, it was so relaxing to sit in the garden."
The gardners Cottage 1 mile from long Island Sound - pet friendly
Historic cottage in Deep River, CT
Exterior

Historic cottage in Deep River, CT

10.0 out of 10, Exceptional, (1)
"Wonderful stay. Charming and perfect. "
$309 nightly
The price is $350
Sep 24 - Sep 25
Total with taxes and fees
Historic cottage in Deep River, CT
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Exterior

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (14)
"The place was great and we enjoyed the fishing."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Outdoor dining

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

10.0 out of 10, Exceptional, (64)
"Loved the salt marsh with all the birds. The views at the beach were amazing! Scott and Mary-Jo were wonderful! I would definitely stay again!"
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Guilford Carriage House at Granite Lodge!
Cottage (1 Bedroom) | Interior

Guilford Carriage House at Granite Lodge!

3.0 star property
9.0 out of 10, Wonderful, (2)
"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!
Adorable Cottage with Cottage porch, walk to water & town
Exterior

Adorable Cottage with Cottage porch, walk to water & town

8.8 out of 10, Excellent, (6)
"Great host and property"
Adorable Cottage with Cottage porch, walk to water & town
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Terrace/patio

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (75)
"This was the best place to celebrate my family member’s 60th! Being right on the water was amazing! We enjoyed the outdoor fire pit, the beachy air and the outdoor setting. Inside was clean and adorable. The bunk beds were much larger than appears in the picture. If you want a little getaway to enjoy the salty air, I highly recommend! The owner was very timely in getting back regarding any questions I had and was friendly. "
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Updated cottage "Beriozka" on Cedar Lake
Exterior

Updated cottage "Beriozka" on Cedar Lake

10.0 out of 10, Exceptional, (12)
"Fantastic cottage. Loved the location. Clean well stocked amenities comfy beds. Would definitely stay here again "
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, (3)
"A perfect stay - John and his family were truly wonderful. The house is attached to thier main house, but also very private and secure. We were in town for a wedding weekend and this was the perfect spot for us - truly a beatuiful property! John was helpful in telling us about all of the local spot and supplying us with everything we needed. His wife even welcomed us with a cheese board and wine! Thanks John and family - we had a great time!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Relax with a beautiful lake view
Exterior

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (21)
"Lovely cottage on beautiful Lake Hayward. Very clean, comfortable accommodations and the view of the lake is stunning. The bathroom was newly renovated and the kitchen was well stocked with everything we needed to make and serve our meals. The host was very responsive and kind. Would highly recommend this property and we hope to return soon! "
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

10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Everything was as described on the listing and the house had everything we needed for our family. It was great to have the grill and a kitchen with all the supplies needed. The area is lovely and quiet with two small but nice private beaches within walking distance"
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Exterior

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

9.8 out of 10, Exceptional, (109)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Waterfront Cottage in Branford
Property grounds

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (97)
"Stunning cottage! Great location. Well-equipped kitchen! Comfy beds. Loved the views! Truly a special place!"
Waterfront Cottage in Branford
DIRECT WATERFRONT PRIVATE BEACH
Outdoor dining

DIRECT WATERFRONT PRIVATE BEACH

9.6 out of 10, Exceptional, (24)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Front of property

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (38)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Good location."
Brian 1-night trip
Posted 19 hours ago
The Capitol Hotel

Find out more about Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
792
Accommodation
109 Cottages
Lowest Price
$218
Highest Price
$1,332

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