Cottages in Middlesex County

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Top Cities in Middlesex County

Beautiful sunrise at the mouth of the Connecticut River, Old Saybrook, Connecticut.
CottagesCottages

Old Saybrook

Old Saybrook
Arrigoni Bridge
CottagesCottages

Cromwell

Cromwell

Our top choices for Middlesex County cottages

Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
North Fork Cottages & RV Resort
Exterior

Waterfront Cottage in Branford

Waterfront Cottage in Branford
branford
10.0 out of 10, Exceptional, (99 reviews)
"Beautiful location "
United States
Anne d.
Waterfront Cottage in Branford
Property grounds

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Pipes Cove
9.8 out of 10, Exceptional, (102 reviews)
"Relaxing stay on beautiful property."
United States
Annie B.
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Terrace/patio

115 Rose Cottage with 2 bedroom walk to Groton Bay

115 Rose Cottage with 2 bedroom walk to Groton Bay
Groton
8.8 out of 10, Excellent, (8 reviews)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
United States
Nicholas C.
115 Rose Cottage with 2 bedroom walk to Groton Bay
Exterior

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
West Haven
9.4 out of 10, Exceptional, (13 reviews)
"Tom is excellent host. Great house, clean and very nicely set up. Great care to details. House comes with everything you need. "
United States
Brandon R.
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Exterior

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
Westbrook Center
9.8 out of 10, Exceptional, (113 reviews)
"Great location, cozy cottage, friendly neighbors, and stunning beaches. There are plenty of places to visit, restaurants to try, and beautiful sunrises and sunsets to enjoy!"
United States
Carol E.
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
Exterior

Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (84 reviews)
"Excellent property and great location. Will stay there again. "
United States
Brian L.
Direct waterfront renovated cottage.
Cottage (1 Bedroom) | Interior

Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!
3.0 star property
Guilford
9.0 out of 10, Wonderful, (2 reviews)
"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"
United States
Anonymous traveler
Guilford Carriage House at Granite Lodge!
Exterior

Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (73 reviews)
"Lovely little cottage in a beautiful area of short beach. Joel the host was very kind and knowledgeable about the area and things to do. Would absolutely stay again. "
United States
Douglas M.
Cozy Home near private beach , close to New Haven area colleges Hospitals
Exterior

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 735
AED 1,305 total
includes taxes & fees
1 Mar - 2 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Cutchogue
10.0 out of 10, Exceptional, (28 reviews)
"We had an amazing stay at this home. The house was exactly as described and was plenty of space for a family of 4 to spend a weekend. We particularly enjoyed the porch and large back yard as well as the proximity to beaches, wineries, and dining. The owner was extremely responsive throughout our stay and made us feel very welcome. Would highly recommend! "
United States
Kathryn P.
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Exterior

Lovely Cottage in the Heart of Long Island Wine country

Lovely Cottage in the Heart of Long Island Wine country
Southold
9.8 out of 10, Exceptional, (30 reviews)
"Perfect for what I needed"
United States
Mike H.
Lovely Cottage in the Heart of Long Island Wine country
Exterior

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
Adorable Cottage with Cottage porch, walk to water & town
Outdoor dining

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
Saybrook Manor
10.0 out of 10, Exceptional, (5 reviews)
"This lovely home was perfect in every way!"
United States
Patricia C.
Charming 3-bedroom cottage short walk to Chalker Beach
Exterior

Direct waterfront cottage on private sandy beach

Direct waterfront cottage on private sandy beach
Morgan Point
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful stay! The backyard beach views couldn’t be better! Great use of cozy space. Will book again if possible!"
United States
Megan
Direct waterfront cottage on private sandy beach
Exterior

Luxury Tiny Home In Niantic

Luxury Tiny Home In Niantic
East Lyme
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic "tiny home" with lots to do and spacious lot/house. We've stayed twice and will be back-"
United States
Joseph P.
Luxury Tiny Home In Niantic
House (3 Bedrooms) | Interior

New Haven Gem w/ Private Pool, Walk to Beach!

New Haven Gem w/ Private Pool, Walk to Beach!
3.0 star property
East Shore
New Haven Gem w/ Private Pool, Walk to Beach!
Exterior

Relax with a beautiful lake view

Relax with a beautiful lake view
Colchester
10.0 out of 10, Exceptional, (22 reviews)
"Great location"
United States
Anonymous traveler
Relax with a beautiful lake view
Exterior

Charming Cottage by the Lake❤️

Charming Cottage by the Lake❤️
Coventry Lake
9.6 out of 10, Exceptional, (21 reviews)
"Nice lake access"
United States
Stephanie Z.
Charming Cottage by the Lake❤️
Exterior

Ritz - East Hampton Cottage On The Water

Ritz - East Hampton Cottage On The Water
East Hampton
9.6 out of 10, Exceptional, (9 reviews)
"Very nice place to stay and close to everything. The available tennis court and kayaks were a great amenity, and it was a treat to walk to S&S in the mornings for coffee."
United States
Matthew K.
Ritz - East Hampton Cottage On The Water
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 Middlesex County Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Overall great stay. Staff was friendly and helpful, room was clean, breakfast was nice, and the gym was well taken care of. We had loud neighbors one night, but we called the desk and the helped us out instantly. Overall, we felt very comfortable here. "
Juan 2-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG