Title: Chester Vacation Packages & Trips 2026 from CA $999 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)

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# Chester Vacation Packages

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#### Your Chester Vacation

Excellent adventures await when you reserve a Chester vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like [DaVallia Art & Accents](https://www.expedia.ca/DaVallia-Art-Accents-Chester-Depot.d553248621532666916.Vacation-Attraction). Your ultimate Chester vacation is just clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.

## Top Chester Vacation Deals

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

![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hideaway Inn Mt. Snow

CA $999

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

8.8/10 Excellent! (69 reviews)

I loved staying here and can’t wait to do so again. The room was clean, cozy and comfortable. Loved the automated check in with clear directions. The entire place was decked out with awesome ambience and decor. I just wish the hot tub was working. It’s so close to Mount Snow too!

Reviewed on Mar 18, 2026

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Latchis Hotel

CA $1,120

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

8.6/10 Excellent! (853 reviews)

The hotel is charming. The location is great. The building is funky, given it's age and need for repair. The staff are friendly, helpful, and knowledgeable. The theater located in the same building is a one of a kind attraction. It was a plus for us that the hotel is owned and run by a nonprofit.

Reviewed on Mar 22, 2026

![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/c3cb22fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shire Woodstock

CA $1,283

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

8.8/10 Excellent! (914 reviews)

Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!

Reviewed on Jan 30, 2026

![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/f7a080fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chalet 239

CA $1,101

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

9.4/10 Exceptional! (113 reviews)

Parking was right in front of the building. The place was very clean all over. Breakfast was included, they served pastries, bagels, yogurt, etc. Super easy check in process. The Chalet is only about a 5 minute drive from mount snow! So grateful to the staff who texted me to let me know we had left something behind and the room when they went to clean it!

Reviewed on Mar 19, 2026

![Jackson Gore Village, A Vail Resorts Property](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

CA $1,124

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

8.6/10 Excellent! (847 reviews)

No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

## Ready to book your vacation to Chester?

Choose your dates

## Chester Hotel Deals

![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Fullerton Inn

40 The Common Chester VT

Fully refundableReserve now, pay when you stay

CA $179

CA $195 total

Apr 3 - Apr 4

includes taxes & fees

8/10 Very Good! (424 reviews)

Yes, little guests easy parking spaces. Restaurant staff were pleasant. Heat didn’t appear until 11PM. A tad chilly. Room was clean.

Reviewed on Mar 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=15845368&PinnedHotelID=15845368&HadPinnedHotel=true&regionId=89014)

![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Stone Hearth Inn and Eatery

698 VT-11 Chester VT

Fully refundableReserve now, pay when you stay

CA $281

CA $307 total

Mar 31 - Apr 1

includes taxes & fees

9.2/10 Wonderful! (116 reviews)

Beautiful place. Rustic and restored beautifully to keep the charm. Talked with the owner over breakfast. Family business with an amazing restaurant. We will stay there again!

Reviewed on Mar 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=87486236&PinnedHotelID=87486236&HadPinnedHotel=true&regionId=89014)

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

CA $190

CA $217 total

Apr 5 - Apr 6

includes taxes & fees

8.8/10 Excellent! (1,006 reviews)

There's a cute little town nearby with a great coffee shop.

Reviewed on Mar 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=1823093&PinnedHotelID=1823093&HadPinnedHotel=true&regionId=89014)

[See all 3,120 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&regionId=89014)

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)

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