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

Middlesex County Vacations & Trips from $605

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Your Middlesex County Vacation

Leave all the planning to us with a Middlesex County vacation package. With everything organized before you leave, the only thing left to do is sit back, relax and experience this destination's countless delights. Begin your trip to Middlesex County with a couple of nights in Old Saybrook visiting popular sights like Westbrook Town Beach and Clinton Crossing Premium Outlets. East Hampton is another city that lures crowds from near and far. TPC River Highlands and Brownstone Exploration & Discovery Park are two of the top places to see here. Expedia is a one-stop shop when it comes to planning your Middlesex County vacation. From accommodations and flights, to car rentals and activities, we're here to help you curate a travel experience like no other.

Top destinations in Middlesex County

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

Old Saybrook

Old Saybrook

The Latest Middlesex County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An outdoor dining area with tables and chairs, surrounded by plants and trees.
    Jan 22 - Jan 24

    Delamar West Hartford + Flight

    West Hartford
    2 nights
    4.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Very clean and the staff was very friendly"
    Reviewed November 10, 2026
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $803
    $605
    per traveler
    found 14 hours ago
    Delamar West Hartford
  • A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.
    Jan 22 - Jan 25

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    3 nights
    5.0 star property
    Roundtrip • Orlando (MCO) - New Haven (HVN)
    MCO - LGA • Nonstop LGA - MCO • 1 stop
    $1,341
    $1,014
    per traveler
    found 1 hour ago
    Beechmont - Perfect for Family Retreat!
  • A modern lounge area with a leather sofa, wooden coffee tables, and a large window providing natural light.
    Dec 28 - Jan 3

    Landing Apartments Downtown New Haven + Flight

    Downtown New Haven
    6 nights
    3.0 star property
    Roundtrip • Atlanta (ATL) - New Haven (HVN)
    ATL - HVN • Nonstop HVN - ATL • Nonstop
    $1,418
    $1,128
    per traveler
    found 1 day ago
    Landing Apartments Downtown New Haven
  • A modern kitchen with a central island, a dining area with chairs, and a view through large windows.
    Dec 28 - Jan 3

    Landing Apartments New Haven Near Dixwell + Flight

    Newhallville
    6 nights
    3.0 star property
    2.0/10 - (1 review)
    "The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host."
    Reviewed May 25, 2026
    Roundtrip • Atlanta (ATL) - New Haven (HVN)
    ATL - HVN • Nonstop HVN - ATL • Nonstop
    $1,630
    $1,322
    per traveler
    found 1 day ago
    Landing Apartments New Haven Near Dixwell
  • A dining area with tables and chairs, large windows with curtains, and a view of a cityscape.
    Dec 28 - Jan 3

    Omni New Haven Hotel at Yale + Flight

    Downtown New Haven
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,126 reviews)
    Roundtrip • Atlanta (ATL) - New Haven (HVN)
    ATL - HVN • Nonstop HVN - ATL • Nonstop
    $1,132
    $922
    per traveler
    found 1 day ago
    Omni New Haven Hotel at Yale

Discover the most popular places to visit in Middlesex County

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard
Open Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
You can spend time browsing the exhibits at Essex Steam Train during your travels in Essex Village. While you're in the area, stroll along the beautiful beaches.
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What to do in Middlesex County

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

$10
per adult
0% of travelers recommend
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Middlesex County

Middlesex County Hotel Deals

A cozy dining area with a brick fireplace, wooden chairs, and tables set for a meal.

Inn at Middletown

Inn at Middletown
3.5 star property
9.2 mi from Middlesex County
8.8 out of 10, Excellent, (683 reviews)
"Location was great as always"
$184 nightly
The price is $208
Dec 13 - Dec 14
Total with taxes and fees
Inn at Middletown
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.
See all properties in Middlesex County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.