Title: Cheshire Vacation Packages & Trips 2026 from CA $598 | Expedia.ca

[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)

![](https://images.trvl-media.com/place/183057/d187e44c-20c9-4663-9d61-d49fc5e6e9f7.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Cheshire Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Tai Bui 

- ##  
Plan, book, travel with confidence
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/Toyota-Presents-Oakdale-Theatre-Wallingford.d6089829.Vacation-Attraction), [Choate Rosemary Hall](https://www.expedia.ca/Choate-Rosemary-Hall-Wallingford.d553248635939586716.Vacation-Attraction) and [Mount Southington Ski Area](https://www.expedia.ca/Mount-Southington-Ski-Area-Plantsville.d6089845.Vacation-Attraction). 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](https://images.trvl-media.com/lodging/2000000/1730000/1721900/1721807/d9e240b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mayflower Motel Milford

CA $598

per person

Feb 17 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to New Haven (HVN)

6/10 (549 reviews)

We are staying here for a few nights to be close to my family. We drove by Mayflower Motel so many times. We always stayed at a hotel that we were familiar with, big named places

Reviewed on Nov 30, 2025

![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Graduate by Hilton New Haven

Downtown New Haven

CA $691

per person

Feb 17 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to New Haven (HVN)

9.2/10 Wonderful! (908 reviews)

Great staff, convenient central location, and tasteful retro-collegiate decor in a renovated historic building.

Reviewed on Jan 1, 2026

![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Motel 6 New Haven - Branford, CT

CA $605

per person

Feb 17 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to New Haven (HVN)

7/10 Good! (1,001 reviews)

The man the helped check me in was super nice. I picked this place because i had an 8am flight & it was very close to the airport. Also the rate was reasonable. The room next door had loud music playing, so i called the front desk. Within 10 - 15 min they turned it down.

Reviewed on Dec 2, 2025

![Super 8 by Wyndham Milford/New Haven](https://images.trvl-media.com/lodging/1000000/870000/866400/866321/f1ba5603_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Super 8 by Wyndham Milford/New Haven

CA $618

per person

Feb 17 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to New Haven (HVN)

5.6/10 (891 reviews)

The room was nice for the price like the fact no tub it's a stand up shower

Reviewed on Jan 2, 2026

![Comfort Inn Naugatuck-Shelton, CT](https://images.trvl-media.com/lodging/2000000/1940000/1932400/1932357/fcd29dce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Comfort Inn Naugatuck-Shelton, CT

CA $647

per person

Feb 17 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to New Haven (HVN)

7.8/10 Good! (729 reviews)

Everything was acceptable, no complaints. Staff was friendly from front desk to maid service.

Reviewed on Jan 6, 2026

## Ready to book your vacation to Cheshire?

Choose your dates

## Cheshire Hotel Deals

![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

New Haven Hotel

229 George Street New Haven CT

Fully refundableReserve now, pay when you stay

9/10 Wonderful! (1,987 reviews)

Customer service is top-notch, they are always very accommodating and friendly. We found the hotel to be very clean, the location is extremely convenient to dining shopping and the areas of New Haven. You would want to explore. Parking is extremely convenient and attached to the hotel. There are ...

Reviewed on Jan 4, 2026

[Get rates](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true&regionId=183057)

[](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true&regionId=183057)

![The Capitol Hotel](https://images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Capitol Hotel

440 Asylum St Hartford CT

Fully refundableReserve now, pay when you stay

CA $117

CA $134 total

Jan 11 - Jan 12

includes taxes & fees

7.4/10 Good! (1,144 reviews)

Yes the room is clean n staff excellent.

Reviewed on Jan 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=6777&PinnedHotelID=6777&HadPinnedHotel=true&regionId=183057)

![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cambria Hotel New Haven University Area

20 Dwight Street New Haven CT

Fully refundable

CA $143

CA $165 total

Feb 8 - Feb 9

includes taxes & fees

8.6/10 Excellent! (1,011 reviews)

clean room, helpful staff

Reviewed on Jan 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true&regionId=183057)

[See all 1,227 properties in Cheshire](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F01%2F2026&endDate=11%2F01%2F2026&regionId=183057)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Explore a world of travel with Expedia

- Lodging
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- [B&B in Cheshire Historic District ](https://www.expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Visit Southington ](https://www.expedia.ca/Southington.dx6795)
- [Sterling Memorial Library at Yale University ](https://www.expedia.ca/Sterling-Memorial-Library-At-Yale-University-Downtown-New-Haven.d6071481.Vacation-Attraction)
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- [Yale University Art Gallery ](https://www.expedia.ca/Yale-University-Art-Gallery-Downtown-New-Haven.d6071487.Vacation-Attraction)
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- [Car rental Meriden ](https://www.expedia.ca/Car-Rentals-In-Meriden.d8818.Car-Rental-Guide)
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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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