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.
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $668, price is now $544 per person
$544
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,169, price is now $928 per person
$928
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Chicago (CHI) 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

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,851, price is now $1,375 per person
$1,375
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Chicago (CHI) 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

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,485, price is now $1,122 per person
$1,122
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $678, price is now $551 per person
$551
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
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.

Top Cheshire hotels deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St. Cheshire CT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $114 total per night
$114 total
Sep 8 - Sep 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.
Parking included
Free WiFi
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Sep 10 - Sep 11
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
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
$126 nightly
The price is $145 total per night
$145 total
Sep 7 - Sep 8
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
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $126 total per night
$126 total
Sep 10 - Sep 11
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.
Pool
Breakfast included
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
510 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $155 total per night
$155 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the express check-in and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
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
$135 nightly
The price is $155 total per night
$155 total
Sep 13 - Sep 14
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.
Breakfast included
Pet friendly
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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 Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
See properties

Frequently asked questions

How much are vacation packages to Cheshire?
You'll find an amazing hotel + flight bundle for as little as $544. 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

A stone tower with a metal gate, surrounded by trees and a stone wall.
A frozen lake with a solitary tree in the foreground and a sunset in the background.
A wooden bridge over a river with a forested area in the background.
A stone tower with American flags in front.
A road flanked by autumn trees with sunlight filtering through.