Middlesex County Vacation Packages 2026 from $480

Search vacation packages deals in Middlesex County's top destinations

Westbrook

Vacations

Middlesex County flight + hotel vacation packages

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

Hotel St. James

Manhattan

Save 100% on your flight

$480

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,831

per person

May 20 - May 25

found 10 hours ago

Roundtrip flight included

Chicago (ORD) 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.

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,551

per person

Apr 22 - Apr 25

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

JW Marriott Essex House New York

Manhattan

Save 100% on your flight

$834

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.

1 Hotel Central Park

Manhattan

$1,724

per person

Apr 27 - May 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

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

Top Middlesex County hotels deals

Inn at Middletown

70 Main Street Middletown CT

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$225 total

Mar 3 - Mar 4

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$104 nightly

$120 total

Mar 3 - Mar 4

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

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$212 total

Apr 1 - Apr 2

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

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

298 E Haddam Moodus Rd East Haddam CT

$149 nightly

$171 total

Mar 3 - Mar 4

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

$97 nightly

$112 total

Mar 22 - Mar 23

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

Hyatt Place Uncasville - Casino Area

2049 Norwich Montville CT

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Breakfast included

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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?

$480 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.