Title: Cheshire Vacation Packages & Trips 2026 from CA $706 | 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)[Things to do in Cheshire](https://expedia.ca/Things-To-Do-In-Cheshire.d183057.Travel-Guide-Activities)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)

![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Cheshire Vacation Packages

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

- ##  
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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](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.

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

CA $706

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

8/10 Very Good! (1,002 reviews)

Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question.

Reviewed on Feb 22, 2026

![James Pharmacy Bed & Breakfast](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### James Pharmacy Bed & Breakfast

Old Saybrook Center

CA $1,066

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

9.2/10 Wonderful! (20 reviews)

Room was pleasant and clean, although small. Bathroom fixtures all new and very clean and functional. Firm bed, which I appreciated. The stairs are steep though there is a firm railing. I didn't realize that we would get a breakfast voucher as opposed to a true B&B experience. The restaurant provided was friendly and the food all looked great but unfortunately didn't have much flavor. The Paperback Cafe nearby had tastier choices. Make sure that you get their email about how to get in because there is no one on site and when we arrived after dark, the front of the building wasn't lit because the entry is in the back. On our first morning, we got a text about our credit card payment not going through. The owner and manager were both responsive but given that they weren't on site, a friendlier tone (i.e., assuming that there might've been a mistake in their information, which there was!) would've been appreciated. It's a lovely place in an excellent location but perhaps slightly expensive given that they are not providing a full B&B experience.

Reviewed on Oct 6, 2025

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Water's Edge Resort & Spa

Westbrook Center

CA $1,095

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

8.8/10 Excellent! (1,002 reviews)

The staff throughout our stay was amazing. Our room was spotless and so comfortable. Beautiful view from the balcony. The spa was beautiful. We had relaxing massages. We ate in the main dining room. Our waiter was great and the food was amazing. We had so much fun using the jacuzzi and the pool which were very clean. So convenient having Starbucks in the hotel and a lovely gift shop. The valet staff were kind and helpful with our luggage. We will definitely stay here again and recommend this hotel for your stay. We went during the cold weather but would love to come back in the warmer weather.

Reviewed on Feb 24, 2026

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Saybrook Point Resort & Marina

Old Saybrook Center

CA $1,221

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

9.4/10 Exceptional! (1,001 reviews)

Staff were so welcoming, knowledgeable and helpful! Room was gorgeous with a perfect view of the marina and the light house; the fireplace and cozy chairs with blankets were great - best to enjoy with a cup of delicious coffee and cake - which we did! We had the best salmon and pork chop of our lives!!! king size bed was comfortable and the bathroom was bright, well-appointed and spacious! Definitely order the breakfast in your room - you will NOT be disappointed! the Saybrook location is central - and allowed us to go thrifting, antiquing and catch the great Jimmy Greene at the Side Door - just 3 miles away from the resort! We are coming back soon!

Reviewed on Feb 17, 2026

![Westbrook Inn B&B](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/46915263_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westbrook Inn B&B

Westbrook Center

CA $1,001

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

9.8/10 Exceptional! (175 reviews)

Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :)

Reviewed on Dec 21, 2025

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_183057)

## 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 refundable

CA $220

CA $253 total

Mar 3 - Mar 4

includes taxes & fees

9/10 Wonderful! (2,018 reviews)

The room was great, I love that it had a separate sink outside of the bathroom. Beds were comfortable and linens cozy.

Reviewed on Feb 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%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 $115

CA $132 total

Mar 1 - Mar 2

includes taxes & fees

7.6/10 Good! (1,185 reviews)

Room was kind of dirty (brown liquid on the wall/curtain/floor), path to garage was not plowed

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%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

Mar 22 - Mar 23

includes taxes & fees

8.8/10 Excellent! (1,021 reviews)

Noise at 4am in room .. load banging .. continued for hours … desk said it was probably ac unit. No help and did nothing to makeup for this .

Reviewed on Feb 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true&regionId=183057)

[See all 1,260 properties in Cheshire](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%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
- Flights
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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)
- [Unionville Vacations ](https://www.expedia.ca/Unionville.d180158.Destination-Travel-Guides)
- [Westfield Connecticut Post Mall ](https://www.expedia.ca/Westfield-Connecticut-Post-Mall-Milford.d6163930.Vacation-Attraction)
- [White Memorial Conservation Center ](https://www.expedia.ca/White-Memorial-Conservation-Center-Litchfield.d553248621532664769.Vacation-Attraction)
- [Yale University Art Gallery ](https://www.expedia.ca/Yale-University-Art-Gallery-Downtown-New-Haven.d6071487.Vacation-Attraction)
- [Yale University ](https://www.expedia.ca/Yale-University-Downtown-New-Haven.d502016.Vacation-Attraction)

- [Car rental Meriden ](https://www.expedia.ca/Car-Rentals-In-Meriden.d8818.Car-Rental-Guide)
- [Car rentals near Quinnipiac University ](https://www.expedia.ca/Car-Rentals-In-Quinnipiac-University.d502014.Car-Rental-Guide)
- [Car rental Wallingford ](https://www.expedia.ca/Car-Rentals-In-Wallingford.d7533.Car-Rental-Guide)
- [Rent A Wreck Rental Cars in Meriden ](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Meriden.d8818-c33.Car-Rental-Guide-Suppliers)

\* 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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