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

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Dates

November 2026

5

December 2026

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Top cities in Middlesex County

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

Check prices for these dates

In two weeks

20 Nov - 22 Nov

In two months

In three months

29 Jan - 31 Jan

In four months

26 Feb - 28 Feb

Map of Middlesex County

Our top choices for Middlesex County holiday rentals

A glass enclosure with a view of a forest interior, including a bed and a small table with items.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

United States

Kelvin

₹19,048 total

includes taxes & fees

6 Dec - 7 Dec

A balcony with a view of the ocean, a lawn, and a house in the background.

2. Cliffside Resort Condominiums

Greenport

United States

William

₹28,808 total

includes taxes & fees

15 Nov - 16 Nov

A modern house with a deck, outdoor seating, and a fire pit.

3. North Fork Resort

Greenport

United States

Altynai

₹33,586 total

includes taxes & fees

16 Nov - 17 Nov

A modern conference room with wooden flooring, grey sofas, a blue ottoman, and a flat-screen TV on the wall.

4. Trumbull Apartments

Downtown Hartford

United States

Nicolas

₹29,090 total

includes taxes & fees

27 Nov - 28 Nov

A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Oakville

₹51,019 total

includes taxes & fees

6 Nov - 7 Nov

A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

6. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton

₹76,281 total

includes taxes & fees

22 Nov - 23 Nov

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Top Middlesex County Hotel Reviews

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

United Kingdom

Jessica

A patio with Adirondack chairs, a fire pit, and a view of a lake.

Westbrook Inn B&B

Westbrook Center

8/10 Good

United Kingdom

Nicola

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

United Kingdom

Chris

A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.

Springhill Suites by Marriott Hartford Cromwell

Cromwell

10/10 Excellent

United Kingdom

Shahzad

A brick building with a sign that reads "Inn at Middletown."

Inn at Middletown

Washington Street Historic District

10/10 Excellent

United Kingdom

Dianne

A sign for Pier Blue Guesthouse with a landscaped garden featuring various shrubs and trees.

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

10/10 Excellent

United Kingdom

Mary

A hotel room with a large bed, two bedside lamps, a wooden nightstand, a desk with a chair, and a view of the outdoors through a window.

Liberty Inn

Old Saybrook

8/10 Good

United Kingdom

SandyE

A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

10/10 Excellent

United Kingdom

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Find out more about Middlesex County

Holiday Apartments in Middlesex County

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