Cheshire Vacation Packages

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Your Cheshire Vacation

There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire vacation packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like Toyota Oakdale Theatre, Choate Rosemary Hall and Mount Southington Ski Area. Expedia will help you escape your daily routine. Tailor your vacation to Cheshire to suit your style of travel, whatever that may look like.

Top Cheshire Vacation Deals

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

Mayflower Motel Milford

2 out of 5
per person
Jul. 7 - Jul. 11
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
5.6/10 (361 reviews)
It’s quiet for the most part and u have stores in walking distance

Reviewed on May 1, 2024

Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
per person
Jul. 7 - Jul. 11
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
5.8/10 (684 reviews)
Exterior door locks not functioning.

Reviewed on May 24, 2024

Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
per person
Jul. 7 - Jul. 11
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
8.2/10 Very Good! (1,002 reviews)
Convenient, right off the highway. Staff was good, hotel was clean.

Reviewed on May 12, 2024

Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
per person
Jul. 7 - Jul. 11
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
6.6/10 (1,004 reviews)
The property is good can’t say nothing bad about it

Reviewed on Feb. 22, 2024

Super 8 by Wyndham Milford/New Haven

Super 8 by Wyndham Milford/New Haven

2 out of 5
per person
Jul. 7 - Jul. 11
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
5.4/10 (659 reviews)
TO MUCH CIGARRET SMELL OUTSIDE

Reviewed on Mar. 23, 2024

Cheshire Hotel Deals

Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is CA $159 per night from May 27 to May 28
CA $159
CA $183 total
includes taxes & fees
May 27 - May 28
8.2/10 Very Good! (862 reviews)
"Good"

Reviewed on Apr. 26, 2024

Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is CA $129 per night from May 29 to May 30
CA $129
CA $149 total
includes taxes & fees
May 29 - May 30
8.4/10 Very Good! (554 reviews)
"Nice new property"

Reviewed on May 13, 2024

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from May 26 to May 27
CA $217
CA $250 total
includes taxes & fees
May 26 - May 27
8.8/10 Excellent! (1,232 reviews)
"Stayed only one night, location was quite close to Yale, within walking distance. Staff was friendly. Room was big but lots of unused space tbh."

Reviewed on May 21, 2024

New Haven Hotel
See all 1,096 properties in Cheshire
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
We make it simple to travel the world, with Cheshire vacation packages starting from just CA $1,071. You’ll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your travel itinerary?
How do I get a cheap travel package to Cheshire?
Track down flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a Cheshire vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 hotel options around the world to choose from, you’ll never be short of choice.
Where should I stay in Cheshire?
With so much to do in Cheshire, it makes sense to book a hotel close to its attractions. Cheshire Golf Course, Cheshire Hollow Farm and Bartlem Park are some popular ones to put on your must-see list.
What are the top hotels in Cheshire?
Whether you plan to stay for just one night or a week in Cheshire, you’ll get a good night’s sleep at Cheshire Welcome Inn. This place is a top pick for plenty of travelers.
How far in advance should I book my Cheshire vacation?
It all depends on the airline, but you can usually compare international fares on Expedia up to 12 months in advance. While it’s generally a good idea to book ahead of time, lucky travelers occasionally find a cheaper flight just weeks prior to the date of departure.
What does an Expedia Cheshire travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Cheshire travel package just how you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Cheshire travel package?
When you book your hotels, flights and car rentals together, you’ll score terrific discounts. Whether you’re organizing a beach break in a villa or want to stay in a fancy hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Cheshire Expedia vacation package?
Yes — that’s one of the best things about an Expedia package. You get to decide. We have access to more than 550 airline partners all over the world, so you have lots of choice when creating your Cheshire trip.
If I'm not able to travel, can I cancel my Cheshire vacation package?
Yes, you can. We realize life happens, so we’re happy to help if you need to make changes to your Cheshire vacation package. It may be possible to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Cheshire

Image for Cheshire Golf Course

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.

Cheshire Golf Course
Image for Cheshire Hollow Farm

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
Image for Barker Character, Comic and Cartoon Museum

Barker Character, Comic and Cartoon Museum

You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area.

Barker Character, Comic and Cartoon Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.