Middlesex County Holiday Rentals: Short-Term Accommodations for Rent

Summer sunset on the Connecticut River, Shoreline, and Long Island Sound in Old Saybrook, CT, with Lynde Lighthouse in the foreground, along with Fenwick, and a colorful summer sunset sky

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Our top choices for Middlesex County holiday rentals

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Gabrielly

HK$1,703 total

includes taxes & fees

1 Jun - 2 Jun

North Fork Resort

Greenport

James

HK$2,909 total

includes taxes & fees

1 Jun - 2 Jun

Cliffside Resort Condominiums

Greenport

Allison

HK$2,161 total

includes taxes & fees

1 Jun - 2 Jun

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Windsor

HK$5,432 total

includes taxes & fees

1 Jun - 2 Jun

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Oakville

HK$4,219 total

includes taxes & fees

30 May - 31 May

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Top Middlesex County Hotel Reviews

Omni New Haven Hotel at Yale

6/10 Okay

"No amenities. 5th Floor room with multiple motorcycles outside thought the evening and night. Long line to check in. No upgrades. Neighborhood needs to get CLEANED UP"

The Capitol Hotel

4/10 Poor

"The sink was clogged so you couldn't run the water continuously or the sink would fill and drain very slowly. The bathroom door wouldn't shut all the way, nor would it even open all the way. While the sheets on the bed were clean, the floor and carpet around the bed and furniture in the room was pretty old and gross and didn't look like it had been vacuumed or cleaned in a long time. The room also smelled like urine. The front desk staff was helpful and pleasant but the actual room was terrible. Stayed only one night."