Book Exclusive Middlesex County Vacation Packages

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Search vacation packages deals in Middlesex County's top destinations

A forested landscape with a winding dirt road and power lines.

Middletown

Vacations
Middletown
Two wooden benches facing a calm body of water under a clear sky.

Clinton

Vacations
Clinton

Middlesex County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $595, price is now CA $555 per person
CA $555
per person
Aug 9 - Aug 12
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free WiFi, free parking, and room service. Popular attractions Tanger Outlets and Crystal Lake Town Park are located nearby.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $717, price is now CA $619 per person
CA $619
per person
Aug 9 - Aug 12
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,531, price is now CA $2,232 per person
CA $2,232
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartford HealthCare Amphitheater and Glenwood Park are located nearby.
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
Price was CA $1,012, price is now CA $963 per person
CA $963
per person
Aug 14 - Aug 17
just found
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quinnipiac River State Park and Wharton Brook State Park are located nearby.
Three Ducks

Three Ducks

2 out of 5
Price was CA $2,486, price is now CA $2,374 per person
CA $2,374
per person
Aug 9 - Aug 12
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) 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.

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
The price is CA $430 per night
CA $430
CA $519 total
Jul 8 - Jul 9
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.
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 $122 per night
CA $122
CA $140 total
Jul 8 - Jul 9
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

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is CA $204 per night
CA $204
CA $300 total
Aug 4 - Aug 5
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.
Kitchen
Pet-friendly
Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave Mystic CT
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
CA $198 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Mystic. Enjoy free parking, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Olde Mistick Village and Mystic Aquarium and Institute for Exploration are located nearby.
Pool
Pet-friendly
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Free cancellation
Reserve now, pay when you stay
The price is CA $218 per night
CA $218
CA $251 total
Aug 4 - Aug 5
includes taxes & fees
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
Pool
Hot tub
The Fox Tower at Foxwoods

The Fox Tower at Foxwoods

3.5 out of 5
350 Trolley Line Blvd Mashantucket CT
The price is CA $241 per night
CA $241
CA $318 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this spa hotel in Mashantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
Pool
Spa
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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.

Stay near popular Middlesex County attractions

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard
Open Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
You can spend time browsing the exhibits at Essex Steam Train during your travels in Essex Village. While you're in the area, stroll along the beautiful beaches.
See properties

Photos of local treasures

Browse Middlesex County vacation photos for more inspiration

A coastal town with a lighthouse, houses, and a river.
A sunset over a lake with a dock and a boat.
A waterfall cascading over rocks in a forested area.
A waterfall cascading over rocks in a forested area.
A row of blooming cherry trees in full bloom.

Frequently asked questions

How much are vacation packages to Middlesex County?
CA $555 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.