Middlesex County Vacations & Trips from $839
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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
Old Saybrook
Middletown
Westbrook
Clinton
Cromwell
Essex
East Hampton
Chester
The Latest Middlesex County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
New Haven Hotel
Downtown New Haven
$839
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (2,355 reviews)
Room is average but more spacious than we thought. AC fan is loud. TV remote is sticky, it might not be wiped and cleaned for a while. Location is good but parking is a problem. Public parking lot charges less if you check out early. Reception people are indifferent and reluctant to introduce details about the hotel.
Reviewed on Oct 7, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$1,069
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (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 on May 25, 2026
Landing Furnished Apartment Near Yale University
Downtown New Haven
$899
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (2 reviews)
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 2026
Find the Best Middlesex County Vacation Packages
Middlesex County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Top Sights | Harveys Beach, Devils Hopyard State Park and Clinton Town Beach |
Middlesex County Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$84 nightly
$97 total
Nov 5 - Nov 6
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"I would not recommend this property. Very expensive -244- for a smelly room, one small packet of shampoo, stained mattress pad."
Reviewed on Oct 4, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$193 nightly
$222 total
Nov 1 - Nov 2
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
$199 nightly
$229 total
Oct 27 - Oct 28
Total with taxes and fees
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.
Stay near popular Middlesex County attractions
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.
Goodspeed Opera House
9.0/10 (18 reviews)
You can make plans for a show at Goodspeed Opera House during your stay in East Haddam. Wander the riverfront and beaches in the area.
Harvey's Beach
8.8/10 (93 reviews)
If a restful vacation is part of your travel plans, Harvey's Beach might be the perfect place to seek out during your trip to Old Saybrook. Visit the shops and spas in this relaxing area.
Photo by Dawn Johnson
Machimoodus State Park
You can take time to visit Machimoodus State Park during your travels to Moodus. Amble around this family-friendly area's riverfront or experience its entertainment venues.
Wesleyan University
8.6/10 (189 reviews)
Enjoy the collegiate vibe when you visit Wesleyan University, during your travels in Middletown. Experience the area's festivals or attend a sporting event.
Clinton Crossing Premium Outlets
8.6/10 (135 reviews)
You can find the perfect gifts to bring home at Clinton Crossing Premium Outlets during your stay in Clinton. While you're in the area, stroll along the beautiful beaches.
TPC River Highlands
6.8/10 (22 reviews)
Enjoy a round of golf in Cromwell at TPC River Highlands. While in this family-friendly area, you can savor the top-notch restaurants.
Westbrook Town Beach
8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
What to do in Middlesex County
Connecticut Coloured Regiment Parade Route: An Audio Tour
$10
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
