Middlesex County Vacations & Trips from $514

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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 rocky beach with large boulders and the ocean in the background.

Old Saybrook

Old Saybrook
A sandy beach with a breakwater, calm sea, and a clear sky.

Westbrook

Westbrook
A forested landscape with a winding dirt road and power lines.

Middletown

Middletown
Two wooden benches facing a calm body of water under a clear sky.

Clinton

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

Cromwell

Cromwell
A quaint white building with a dark shingled roof, a flag, and a sign reading "Toys Ahoy".

Essex

Essex
A forested hillside with autumn foliage.

East Hampton

East Hampton

The Latest Middlesex County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

Downtown New Haven
$514
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,072 reviews)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

North End
$1,580
per person
Oct 24 - Oct 29
found 17 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews
Las Flores Villa

Las Flores Villa

Save 100% on your flight
$4,781
per person
Sep 26 - Sep 30
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
10/10 Exceptional! (1 review)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

Newhallville
Save 100% on your flight
$883
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

The Hill
Save 100% on your flight
$883
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.

Reviewed on Aug 10, 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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
$99 nightly
$114 total
Aug 19 - Aug 20
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Great location & convenient to everything. Shawn (I believe his name was) was so helpful & friendly! Older place but was good for 1 night."

Reviewed on Aug 12, 2026

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$266 nightly
$306 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"Great staff Multiple food and drink options"

Reviewed on Aug 12, 2026

Water's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

298 E Haddam Moodus Rd East Haddam CT
$215 nightly
$247 total
Aug 18 - Aug 19
Total with taxes and fees
9.4/10 Exceptional! (177 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."

Reviewed on Aug 9, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,482 properties in Middlesex County
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

A steam locomotive with the number 40 on its front, traveling on a railway track.
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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A suspension bridge over a body of water, a large white building with a tower, and a forested hill in the background.

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.
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A wooden boardwalk leading to a beach at sunset.

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.
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A large white building with columns and a central staircase.

Wadsworth Mansion

Learn about the local history of Middletown when you take a trip to Wadsworth Mansion. Experience the area's entertainment venues and festivals.
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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.
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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.
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Westbrook Town Beach

8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
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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.
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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
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Middlesex County
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