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.
The Best Way Inn

The Best Way Inn

2 out of 5
West New Haven
Price was $487, price is now $407 per person
$407
per person
Oct 8 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Donald J. Trump Intl. Airport (PBI) to New Haven (HVN)
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
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 $1,216, price is now $895 per person
$895
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $950, price is now $740 per person
$740
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Denver (DEN) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,072, price is now $848 per person
$848
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,185, price is now $996 per person
$996
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.

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
Jul 20 - Jul 21
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

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $155 total per night
$155 total
Aug 9 - Aug 10
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
Aug 12 - Aug 13
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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
$91 nightly
The price is $104 total per night
$104 total
Aug 2 - Aug 3
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.
Pool
Breakfast included
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
$142 nightly
The price is $163 total per night
$163 total
Aug 9 - Aug 10
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
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $129 total per night
$129 total
Jul 26 - Jul 27
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
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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 $407. 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.