Cheshire Vacation Packages 2026 from $499

Cheshire flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Heritage Hotel, Golf & Conference Center

$499

per person

Jul 17 - Jul 20

found 18 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,680

per person

Jul 17 - Jul 20

found 18 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$1,188

per person

Aug 7 - Aug 10

found 21 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Hyatus Luxury Residences City Crossing

The Hill

$1,070

per person

Aug 7 - Aug 10

found 21 hours 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.

Landing Apartments New Haven Near Dixwell

Newhallville

$1,007

per person

Aug 7 - Aug 10

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This apartment includes free WiFi in public areas and a virtual front desk.

Top Cheshire hotels deals

Cheshire Welcome Inn

1106 S Main St. Cheshire CT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$114 total

Jul 1 - Jul 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Parking included

Free WiFi

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$121 total

Jun 14 - Jun 15

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

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$65 nightly

$75 total

Jun 30 - Jul 1

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

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

Jun 14 - Jun 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$82 total

Jun 21 - Jun 22

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pet friendly

Parking included

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$165 total

Jun 21 - Jun 22

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

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.

Popular places to visit

Roaring Brook Park

Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.

Maplecroft Plaza Shopping Center

You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene.

Frequently asked questions

How much are vacation packages to Cheshire?

You'll find an amazing hotel + flight bundle for as little as $499. With one of our Travelocity vacation packages, a stay in Cheshire has never looked more irresistible! Save both time and money and then get a start on packing those bags.

How long should my Cheshire vacation be?

There are no firm rules when it comes to how long you should spend in Cheshire, but most people stay around 3 nights. Got some wiggle room in your departure date? Consider treating yourself to an extra night or two. Then you'll have enough time to check out the area's hidden treasures as well.

Where can I get the best vacation package deals for Cheshire?

For an amazing package deal to Cheshire, nothing compares to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties worldwide to create the ultimate escape — it couldn't be easier than that.

Why should I book my Cheshire vacation bundle with Travelocity?

We offer experiences to suit every type of globetrotter, top-quality service and 24/7 customer support. And to top all that off, we'll match any better price you find with our Price Match Guarantee.

Can I save on my Cheshire car rental if I combine it with a hotel or flight?

With a Cheshire vacation package, you can bundle your car, flight and hotel bookings and save a ton. If you'd love to explore the best of this wonderful location, why not check out Times Square? This popular sight is 75 mi from Cheshire. With your own wheels, you'll be there in the blink of an eye.

Which airport is best for Cheshire?

Many visitors choose to fly into Bradley Intl. Airport (BDL), 30 mi north of downtown Cheshire. Others prefer MacArthur Airport (ISP) (50 mi away from central Cheshire) or Tweed - New Haven Regional Airport (HVN) (17 mi away from central Cheshire).

What is there to do in Cheshire?

Cheshire is overflowing with things to see and do, including Cheshire Golf Course and Cheshire Hollow Farm. These two popular attractions are at the top of most tourists' must-see lists.

Where should I stay when visiting Cheshire?

Many travelers spend their nights at the Holiday Inn Cheshire - Southington, an IHG Hotel. It's a great base for your Cheshire escape.