Deals on vacations and trips to Middlesex County

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A sandy beach with a breakwater, calm sea, and a clear sky.

Westbrook

Vacations
Westbrook

Middlesex County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,004, price is now $767 per person
$767
per person
Oct 19 - Oct 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
A gym is featured at this apartment, along with free WiFi in public areas and laundry facilities. A virtual front desk are provided for your convenience.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,425, price is now $1,027 per person
$1,027
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,804, price is now $1,329 per person
$1,329
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $1,095, price is now $813 per person
$813
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,744, price is now $2,103 per person
$2,103
per person
Oct 17 - Oct 23
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

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
$83 nightly
The price is $95 total per night
$95 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
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
$218 nightly
The price is $251 total per night
$251 total
Oct 7 - Oct 8
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.
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
$175 nightly
The price is $201 total per night
$201 total
Sep 17 - Sep 18
Total with taxes and 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
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $105 total per night
$105 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
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
$164 nightly
The price is $188 total per night
$188 total
Oct 7 - Oct 8
Total with taxes and fees
This hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 20 restaurants.
Pool
Spa
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
$127 nightly
The price is $146 total per night
$146 total
Sep 27 - Sep 28
Total with taxes and fees
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pet friendly
Free WiFi
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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?
$767 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.

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