Middlesex County Vacation Packages 2026 from $403

Search vacation packages deals in Middlesex County's top destinations

This photo was taken during a nice fall weekend. The water level was low enough to cross to the other side to capture the falls from a different angle than most. Best time however is early morning before most people get there.

Middletown

Vacations

Essex

Vacations

Middlesex County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Alameda Highline

Manhattan

$403

per person

Mar 22 - Mar 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Limo/town car service, dry cleaning, and luggage storage are also on offer.

Topping Rose House

$551

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

INNSiDE by Meliá New York Nomad

Manhattan

$548

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,141

per person

Mar 9 - Mar 13

found 17 hours ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

The Inn At Fox Hollow Hotel

$618

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Top Middlesex County hotels deals

Inn at Middletown

70 Main Street Middletown CT

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$219 total

Feb 8 - Feb 9

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$281 total

Jan 15 - Jan 16

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

On private beach

Pool

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

Jan 15 - Jan 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Pet friendly

Parking included

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

298 E Haddam Moodus Rd East Haddam CT

$149 nightly

$171 total

Jan 15 - Jan 16

Total with taxes and fees

Stay at this cabin in East Haddam. Enjoy free parking, patios, and climate control. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.

Kitchen

Pet friendly

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$120 total

Jan 25 - Jan 26

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pet friendly

Free WiFi

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$102 total

Jan 15 - Jan 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

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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.

Photos of local treasures

Browse Middlesex County vacation photos for more inspiration

Chapman Falls at Devil's Hopyard State Park in CT. The falls are just a short walk from the parking lot. This photo was taken in the Spring but in the summer you can swim here.

Lyman orchards is lovely any time of year, but especially in spring when the apples and peaches are in bloom. These are their peach trees. Plus, Lyman orchard's store has great cider, sandwiches, and snacks.

Frequently asked questions

How much are vacation packages to Middlesex County?

$403 is all you'll need for a memorable vacation in Middlesex County. Bundle your hotel and flights into a vacation package with Travelocity and watch the savings start to grow. With prices as good as these, there's never been a better time to travel.

Where can I get the best vacation package deals for Middlesex County?

There are fantastic Middlesex County package deals to be gained with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Remember this the next time you're ready to tick another place off your must-visit list.

Why should I purchase my Middlesex County vacation bundle with Travelocity?

Because we believe in crafting one-of-a-kind vacation experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our support team is on hand 24/7 to make sure you're never alone. We also offer a Price Match Guarantee, so you can lock in your vacation knowing you've landed the best deal around. How? If you find a lower price, we'll match it!

Will I save money on my Middlesex County car rental if I combine it with hotels and flights?

You sure can with our Middlesex County vacation packages. With one of these, there are loads of ways to make your vacation budget go further. Combine any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With your own ride, all the main sights around Middlesex County are just a road trip away.

Which airport is best for Middlesex County?

Bradley Intl. Airport (BDL) is where many visitors choose to touch down. Depending on your Middlesex County itinerary, T.F. Green Airport (PVD) and MacArthur Airport (ISP) are other choices for you to consider.

What is there to do in Middlesex County?

Middlesex County has hidden surprises at every corner, however make sure you visit TPC River Highlands and Clinton Crossing Premium Outlets during your stay. These attractions shouldn't be missed.