Middlesex County Vacation Packages 2026 from $499

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.

Heritage Hotel, Golf & Conference Center

$499

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,680

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$800

per person

Aug 7 - Aug 11

found 22 hours ago

Roundtrip non-stop flight included

Hot Springs (HOT) to New Haven (HVN)

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 is also provided.

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$1,188

per person

Aug 7 - Aug 10

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.

Hyatus Luxury Residences City Crossing

The Hill

$1,070

per person

Aug 7 - Aug 10

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

Top Middlesex County hotels deals

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$314 nightly

$361 total

Jun 17 - Jun 18

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

$109 nightly

$126 total

Jun 15 - Jun 16

Total with taxes and fees

Pet friendly

Parking included

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

298 E Haddam Moodus Rd East Haddam CT

$175 nightly

$201 total

Jul 13 - Jul 14

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

$122 nightly

$140 total

Jul 6 - Jul 7

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

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$67 nightly

$77 total

Jul 13 - Jul 14

Total with taxes and fees

A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.

Pet friendly

Parking included

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$134 total

Jun 15 - Jun 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

Summer sunset on the Connecticut River, Shoreline, and Long Island Sound in Old Saybrook, CT, with Lynde Lighthouse in the foreground, along with Fenwick, and a colorful summer sunset sky

Frequently asked questions

How much are vacation packages to Middlesex County?

$499 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.