Cheshire Vacation Packages 2026 from $427

Cheshire flight + hotel vacation packages

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

New Haven Hotel

Downtown New Haven

$427

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Jacksonville (JAX) 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.

Landing Apartments New Haven Near Dixwell

Newhallville

Save 100% on your flight

$710

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Jacksonville (JAX) to New Haven (HVN)

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

Landing Furnished Apartments near YSM

Downtown New Haven

$579

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Jacksonville (JAX) to New Haven (HVN)

A gym is featured at this apartment, along with free WiFi in public areas and a virtual front desk.

Landing Furnished Apartment Near Yale University

Downtown New Haven

$518

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Jacksonville (JAX) 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.

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$1,189

per person

Aug 20 - Aug 23

found 12 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.

Top Cheshire hotels deals

Cheshire Welcome Inn

1106 S Main St. Cheshire CT

$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.

The Capitol Hotel

440 Asylum St Hartford CT

$105 nightly

$120 total

Jun 28 - Jun 29

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.

New Haven Hotel

229 George Street New Haven CT

$126 nightly

$144 total

Jul 5 - Jul 6

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.

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

$72 nightly

$83 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.

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT

$66 nightly

$76 total

Jul 8 - Jul 9

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.

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT

$103 nightly

$119 total

Jun 28 - Jun 29

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

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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 Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and 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 $427. 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.