Middlesex County Vacations & Trips from $503
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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
Cromwell
Essex
Chester
Westbrook
Middletown
Clinton
East Hampton
The Latest Middlesex County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartment Near Yale University
Downtown New Haven
$503
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
2/10 (1 review)
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
Hyatus Luxury Residences City Crossing
The Hill
$526
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.4/10 Exceptional! (34 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
Landing Apartments New Haven Near Dixwell
Newhallville
$931
per person
Dec 17 - Dec 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) 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
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
$534
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.6/10 Exceptional! (88 reviews)
Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”!
I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!
Reviewed on Sep 18, 2026
Head of Pond House
$570
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to New Haven (HVN)
10/10 Exceptional! (13 reviews)
The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.
Reviewed on Sep 23, 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 refundable
$78 nightly
$90 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (1,014 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but ..."
Reviewed on Sep 27, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$218 nightly
$251 total
Oct 4 - Oct 5
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
$184 nightly
$211 total
Oct 13 - Oct 14
Total with taxes and fees
9.4/10 Exceptional! (194 reviews)
"It was AMAZING! What a perfect place to reconnect with your partner. We had everything we needed and with the nor’easter, we were cozy up, having a few glasses of wine and playing games and cooking together. We can’t wait to come back! The place was clean, safe, and not a far drive from home."
Reviewed on Sep 27, 2026
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.
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.
Westbrook Town Beach
8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
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.
General Mansfield House
You can spend time studying the exhibits at General Mansfield House during your travels in Middletown. Experience the festivals and entertainment venues in this family-friendly area.
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.