Book Exclusive Middlesex County Vacation Packages

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Bright colors of autumn. View above. Road in the forest. Middletown, Connecticut

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Clinton

Middlesex County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $1,145, price is now CA $881 per person
CA $881
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Three Ducks

Three Ducks

2 out of 5
Price was CA $4,310, price is now CA $2,908 per person
CA $2,908
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Westhampton (FOK)
Stay at this hotel in Westhampton. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions The Great Lawn and Westhampton Beach Performing Arts Center are located nearby.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was CA $1,073, price is now CA $907 per person
CA $907
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Seabluff Beach and Bradley Point Beach are located nearby.
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was CA $3,325, price is now CA $2,871 per person
CA $2,871
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
Book a stay at this beach hotel in Madison. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Hammonasset Beach State Park and Madison Green Historic District are located nearby.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was CA $1,189, price is now CA $1,057 per person
CA $1,057
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Plus Studio and Louis' Lunch are located nearby.

Top Middlesex County hotels deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free cancellation
Reserve now, pay when you stay
The price is CA $293 per night
CA $293
CA $360 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
On private beach
Pool
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free cancellation
The price is CA $121 per night
CA $121
CA $139 total
Jun 7 - Jun 8
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Pet-friendly
Parking included
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is CA $186 per night
CA $186
CA $277 total
Jun 22 - Jun 23
includes taxes & 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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $189 total
May 24 - May 25
includes taxes & fees
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and Louis' Lunch are located nearby.
Pet-friendly
Free WiFi
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Free cancellation
Reserve now, pay when you stay
The price is CA $135 per night
CA $135
CA $155 total
Jun 10 - Jun 11
includes taxes & fees
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located nearby.
Pool
Breakfast included
Great Wolf Lodge Mashantucket

Great Wolf Lodge Mashantucket

2 out of 5
201 Rainmaker Dr Mashantucket CT
Free cancellation
Reserve now, pay when you stay
The price is CA $302 per night
CA $302
CA $392 total
May 25 - May 26
includes taxes & fees
Book a stay at this family-friendly hotel in Mashantucket. Enjoy free WiFi, 4 indoor pools, and 3 restaurants. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
Pool
Hot tub
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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
Middlesex County
Middlesex County
Middlesex County
Middlesex County

Frequently asked questions

How much are vacation packages to Middlesex County?
CA $881 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.