A coastal town with a lighthouse, houses, and a river.

Cottages in Middlesex County

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Top Cities in Middlesex County

A steel bridge with a truss design spanning over a calm river, surrounded by lush greenery.
CottagesCottages

Cromwell

Cromwell
A rocky beach with large boulders and the ocean in the background.
CottagesCottages

Old Saybrook

Old Saybrook

Our top choices for Middlesex County cottages

Balcony

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (45 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AED 1,167
AED 1,333 total
includes taxes & fees
7 Sep - 8 Sep
North Fork Resort
Exterior

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 423
AED 828 total
includes taxes & fees
8 Sep - 9 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

3. 2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard
Westbrook Center
9.6 out of 10, Exceptional, (12 reviews)
"Great Vacation, everything just as described. The owner is very nice and accommodating. Will definitely be back!"
United States
Dana S.
2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard
Exterior

4. Carriage House at 26 Pearl: Private Suite, 3 Minute Walk Downtown & Pet Friendly

Carriage House at 26 Pearl: Private Suite, 3 Minute Walk Downtown & Pet Friendly
Mystic River Historic District
9.8 out of 10, Exceptional, (124 reviews)
"Lovely cottage, clean, well-maintained, extremely convenient to downtown Mystic and Mystic Seaport. Wonderful stay!"
United States
Jeremy H.
Carriage House at 26 Pearl: Private Suite, 3 Minute Walk Downtown & Pet Friendly
Exterior

5. '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, (120 reviews)
"Great location, lovley property, exllent host!"
United States
Bill K.
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Terrace/patio

6. Enchanted Waterfront Cottage

Enchanted Waterfront Cottage
Old Lyme
9.0 out of 10, Wonderful, (20 reviews)
"Easy process, owner was very responsive!"
United States
Colleen C.
Enchanted Waterfront Cottage
Property grounds

7. Carriage House at 26 Pearl: Private Suite, 3 Min Walk Downtown, Pet Friendly

Carriage House at 26 Pearl: Private Suite, 3 Min Walk Downtown, Pet Friendly
Mystic River Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Our pup loved the space, and so did her parents! Great location, great time walking the town."
United States
Tina B.
Carriage House at 26 Pearl: Private Suite, 3 Min Walk Downtown, Pet Friendly
Exterior

8. Charming 1920's no frills cottage in peaceful Old Saybrook

Charming 1920's no frills cottage in peaceful Old Saybrook
Old Saybrook
10.0 out of 10, Exceptional, (5 reviews)
"Perfect cottage for a long weekend getaway for my husband and I! Location is great and the cottage was very clean and well appointed. Jodi was a pleasure to deal with and reached out during our stay to see if we needed anything. We would definitely stay here again when we are in the are!"
United States
Meg D.
Charming 1920's no frills cottage in peaceful Old Saybrook
Exterior

9. Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Clinton
10.0 out of 10, Exceptional, (89 reviews)
"Responded very quickly, everything was clean, place was perfect for a weekend getaway "
United States
Sarah B.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

10. Waterfront! The Perfect Cozy Cottage in Old Lyme, CT

Waterfront! The Perfect Cozy Cottage in Old Lyme, CT
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"Was a great stay very cute property and quiet neighborhood. Stores nearby and easy to access. Friendly and helpful host."
United States
Jessica H.
Waterfront! The Perfect Cozy Cottage in Old Lyme, CT
Exterior

11. Charming Cottage by the Lake❤️

Charming Cottage by the Lake❤️
Coventry Lake
9.4 out of 10, Exceptional, (30 reviews)
"Great place! Would definitely stay again! "
United States
Sam F.
Charming Cottage by the Lake❤️
House (3 Bedrooms) | Front of property

12. 2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
3.0 star property
Madison
10.0 out of 10, Exceptional, (1 review)
"Excellent. The property was simply lovely and the owner was excellent to work with. Location was just what we were looking for, the yard was large and landscaping & outdoor areas were wonderful. Thank you!"
United States
Cindie
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Terrace/patio

13. 4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Westbrook
9.8 out of 10, Exceptional, (86 reviews)
"Great location and service."
United States
Richard P.
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Exterior

14. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is AED 529
AED 1,156 total
includes taxes & fees
7 Sep - 8 Sep
Lakeview Carriage House with Spectacular Sunset Views
Terrace/patio

15. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, Exceptional, (39 reviews)
"I had a pleasant stay, the house is very clean, well-equipped, and the peace and quiet were perfect. I commend the owner."
United States
Faniola O.
Private Guest House w/ Deck + Spectacular Views!
Exterior

16. Wonderful location, walk to beach, private yard, Voted #1 in town by AB&B

Wonderful location, walk to beach, private yard, Voted #1 in town by AB&B
Saybrook Manor
9.4 out of 10, Exceptional, (76 reviews)
"Had a great stay at the property! Great location and you can see the care put into the house! It was the perfect spot for our excursions up the coast!"
United States
Peter S.
Wonderful location, walk to beach, private yard, Voted #1 in town by AB&B
Exterior

17. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is AED 2,336
AED 3,731 total
includes taxes & fees
18 Aug - 19 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

18. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AED 446
AED 587 total
includes taxes & fees
16 Aug - 17 Aug
The Tiny Cottage & Mini Farm
Exterior

19. Beach duplex—2 full homes with private access, backyard, and ocean views!

Beach duplex—2 full homes with private access, backyard, and ocean views!
Clinton
10.0 out of 10, Exceptional, (28 reviews)
"This was a great location- right by the beach- the house was super clean and well stocked. The backyard was a huge plus and our family enjoyed playing corn hole and relaxing out back. "
United States
Robin L.
Beach duplex—2 full homes with private access, backyard, and ocean views!
Exterior

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (26 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 735
AED 1,308 total
includes taxes & fees
1 Sep - 2 Sep
The gardners Cottage 1 mile from long Island Sound - 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.
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Top Middlesex County Hotel Reviews

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"Excellent service great staff"
David 4-night trip
Posted 7 hours ago
Motel 6 New Haven - Branford, CT

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