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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Middlesex County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was CA $2,119, price is now CA $1,830 per person
CA $1,830
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,933, price is now CA $2,023 per person
CA $2,023
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $2,201, price is now CA $1,900 per person
CA $1,900
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to New Haven (HVN)
Stay at this hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Art Plus Studio and Harkness Tower are located nearby.
Three Ducks

Three Ducks

2 out of 5
Price was CA $2,578, price is now CA $2,240 per person
CA $2,240
per person
Jul 12 - Jul 15
found 21 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 $293 per night
CA $293
CA $361 total
May 31 - Jun 1
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 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is CA $199 per night
CA $199
CA $292 total
Jun 25 - Jun 26
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 $189 per night
CA $189
CA $217 total
Jun 7 - Jun 8
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 White Space Gallery 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 $151 per night
CA $151
CA $173 total
Jun 9 - Jun 10
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 $393 total
May 28 - May 29
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.
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
The price is CA $142 per night
CA $142
CA $164 total
May 28 - May 29
includes taxes & fees
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PeoplesBank Arena and Bushnell Park 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.

Photos of local treasures

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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 $1,830 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.