Middlesex County Vacation Packages 2026 from $396

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.

Omni New Haven Hotel at Yale

Downtown New Haven

$396

per person

Aug 7 - Aug 10

found 10 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to New Haven (HVN)

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

Hyatus Luxury Residences City Crossing

The Hill

Save 100% on your flight

$600

per person

Aug 7 - Aug 10

found 10 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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.

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

Save 100% on your flight

$710

per person

Aug 7 - Aug 10

found 10 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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.

Madison Beach Hotel

Madison Center

Save 100% on your flight

$2,356

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip flight included

West Palm Beach (PBI) to New Haven (HVN)

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

Landing Apartments New Haven Near Dixwell

Newhallville

Save 100% on your flight

$588

per person

Aug 7 - Aug 10

found 10 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to New Haven (HVN)

This apartment includes free WiFi in public areas and a virtual front desk.

Top Middlesex County hotels deals

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$295 nightly

$339 total

Jun 9 - Jun 10

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

$102 nightly

$117 total

Jun 7 - Jun 8

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

$189 nightly

$217 total

Jun 4 - Jun 5

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

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$123 total

Jun 28 - Jun 29

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

New Haven Hotel

229 George Street New Haven CT

$124 nightly

$143 total

Jun 14 - Jun 15

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

$105 nightly

$121 total

Jun 16 - Jun 17

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

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?

$396 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.