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.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $1,128, price is now CA $1,123 per person
CA $1,123
per person
Nov 14 - Nov 17
found 6 hours ago
Roundtrip flight included
Terrace (YXT) to New Haven (HVN)
Book a stay at this golf hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hartford HealthCare Amphitheater and Stratford Historical Society Capt David Judson House are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,717, price is now CA $1,933 per person
CA $1,933
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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 Svihra Park are located nearby.
Head of Pond House

Head of Pond House

3 out of 5
Price was CA $3,224, price is now CA $2,775 per person
CA $2,775
per person
Oct 4 - Oct 10
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this business-friendly B&B in Water Mill. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Hamptons Beaches and Cooper's Beach are located nearby.
Three Ducks

Three Ducks

2 out of 5
Price was CA $3,064, price is now CA $2,783 per person
CA $2,783
per person
Oct 4 - Oct 10
found 10 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

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 $120 per night
CA $120
CA $138 total
Aug 23 - Aug 24
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
Free cancellation
Reserve now, pay when you stay
The price is CA $321 per night
CA $321
CA $393 total
Sep 14 - Sep 15
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 $186 per night
CA $186
CA $340 total
Sep 21 - Sep 22
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.
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 $129 per night
CA $129
CA $149 total
Sep 2 - Sep 3
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
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free cancellation
The price is CA $87 per night
CA $87
CA $101 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Branford Supply Pond and Polished are located nearby.
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 $189 per night
CA $189
CA $217 total
Aug 30 - Aug 31
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.
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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 $1,123 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.