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 Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $925, price is now $699 per person
$699
per person
Oct 1 - Oct 4
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,351, price is now $917 per person
$917
per person
Oct 15 - Oct 18
just found
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,117, price is now $787 per person
$787
per person
Oct 15 - Oct 18
just found
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,159, price is now $867 per person
$867
per person
Oct 15 - Oct 18
just found
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,299, price is now $998 per person
$998
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

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
$104 nightly
The price is $120 total per night
$120 total
Aug 4 - Aug 5
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
$314 nightly
The price is $361 total per night
$361 total
Aug 26 - Aug 27
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
$215 nightly
The price is $247 total per night
$247 total
Aug 3 - Aug 4
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
$122 nightly
The price is $140 total per night
$140 total
Jul 30 - Jul 31
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
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$75 nightly
The price is $86 total per night
$86 total
Aug 2 - Aug 3
Total with taxes and fees
A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.
Pet friendly
Parking included
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
$105 nightly
The price is $121 total per night
$121 total
Aug 4 - Aug 5
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
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?
$699 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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