Deals on vacations and trips to Cheshire

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Cheshire flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $516, price is now $389 per person
$389
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
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 and barbecue grills are also provided.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,135, price is now $864 per person
$864
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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 $1,092, price is now $844 per person
$844
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $664, price is now $528 per person
$528
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $609, price is now $496 per person
$496
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.

Top Cheshire hotels deals

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
$133 nightly
The price is $153 total per night
$153 total
Apr 26 - Apr 27
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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $115 total per night
$115 total
May 3 - May 4
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $97 total per night
$97 total
Apr 29 - Apr 30
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
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Apr 26 - Apr 27
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 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $172 total per night
$172 total
May 11 - May 12
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.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$72 nightly
The price is $83 total per night
$83 total
Apr 22 - Apr 23
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.
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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 Falls in the forest

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.

Roaring Brook Park

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.

Cheshire Hollow Farm

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.

Maplecroft Plaza Shopping Center

Frequently asked questions

How much are vacation packages to Cheshire?
You'll find an amazing hotel + flight bundle for as little as $389. 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.

Photos of local treasures

Browse Cheshire vacation photos for more inspiration

Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.
Golden sunlight shining on curved Wooden boardwalk over stream near forest
Castle Craig at Hubbard Park, Meriden, CT. American flags in the foreground and an easily replaceable sky.
Cheshire