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.
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
Price was CA $668, price is now CA $597 per person
CA $597
per person
Nov 10 - Nov 13
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
Book a stay at this boutique hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Vicinanza Studios & Gallery and Hollow Park are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was CA $3,296, price is now CA $1,871 per person
CA $1,871
per person
Dec 10 - Dec 13
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Beardsley Zoo and Lafayette Park are located nearby.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,339, price is now CA $1,186 per person
CA $1,186
per person
Dec 4 - Dec 6
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
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
Saybrook Manor
Price was CA $938, price is now CA $867 per person
CA $867
per person
Dec 4 - Dec 6
found 1 hour ago
Roundtrip non-stop 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.
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
Price was CA $687, price is now CA $635 per person
CA $635
per person
Nov 10 - Nov 13
found 1 hour ago
Roundtrip flight included
Montreal (YUL) 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.

Top Middlesex County hotels deals

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
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $134 total
Oct 12 - Oct 13
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
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 $224 per night
CA $224
CA $282 total
Nov 1 - Nov 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
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 $193 per night
CA $193
CA $287 total
Nov 4 - Nov 5
includes taxes & fees
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
Kitchen
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 $132 per night
CA $132
CA $152 total
Oct 7 - Oct 8
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 Great Wolf Lodge Water Park 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
Free cancellation
Reserve now, pay when you stay
The price is CA $184 per night
CA $184
CA $252 total
Oct 19 - Oct 20
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 Tanger Outlet Foxwoods are located nearby.
Pool
Spa
Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

2.5 out of 5
269 North Frontage Road New London CT
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $130 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this family-friendly hotel in New London. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Connecticut College Arboretum and Old Town Mill are located nearby.
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.

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 $597 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.