Title: Chester Vacation Packages 2026 from $506 | Expedia.com

[Chester Hotels](https://expedia.com/Destinations-In-Chester.d553248635976006029.Hotel-Destinations)[Vacation Rentals in Chester](https://expedia.com/Destinations-In-Chester.d553248635976006029.Vacation-Rental-Destinations)[Car Rentals in Chester](https://expedia.com/Destinations-In-Chester.d553248635976006029.Car-Rental-Destinations)

![](https://images.trvl-media.com/place/58468/788f97e5-e50c-463d-a4aa-1233b00784f7.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chester Vacations & Trips from $506

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

Photo by Rachel Kent

## Your Chester Vacation

Make planning your next getaway quick and easy with a Chester vacation package. Whether it's nature, history or something else entirely that lures you here, our package deals will help you experience it all. Why not organize your trip to Chester around its top cities? [Western Shore](https://www.expedia.com/Western-Shore.d181860.Destination-Travel-Guides), [Bayswater](https://www.expedia.com/Bayswater.d6353709.Destination-Travel-Guides) and [Blandford](https://www.expedia.com/Blandford.d6222262.Destination-Travel-Guides) are all great places to start. Start packing your suitcase, because your Chester vacation is only clicks away with Expedia.

## Top destinations in Chester

![Point Riche Lighthouse sits at the western tip of the Point Riche peninsula near Port au Choix National Historic Site, overlooking the Gulf of St Lawrence. ](https://images.trvl-media.com/place/181860/d0311923-c0f1-4d1d-807b-ba209ddf97a3.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Western Shore

[](https://expedia.com/Western-Shore.d181860.Destination-Travel-Guides)

![Chester featuring a house and a small town or village](https://images.trvl-media.com/place/58468/563e3b62-f804-4c09-b542-8c6504d90bff.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Chester

[](https://expedia.com/Chester.d58468.Destination-Travel-Guides)

![Selfie.... ;-)](https://images.trvl-media.com/place/6309731/2e4ee302-2431-4617-8b01-fff3572d27c8.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Bayswater

[](https://expedia.com/Bayswater.d6353709.Destination-Travel-Guides)

## The Latest Chester Vacation Packages

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

![Hearthstone Inn Boutique Hotel Halifax - Dartmouth](https://images.trvl-media.com/lodging/1000000/20000/12000/11975/2ecf241c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hearthstone Inn Boutique Hotel Halifax - Dartmouth

$506

per person

Mar 23 - Mar 25

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

7.4/10 Good! (1,004 reviews)

The front desk at night was exceptional! The day staff was missing the ironing board.

Reviewed on Feb 2, 2026

![Sandman Signature Dartmouth Hotel & Suites](https://images.trvl-media.com/lodging/93000000/92620000/92611400/92611337/ea92b4a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sandman Signature Dartmouth Hotel & Suites

$533

per person

Mar 23 - Mar 25

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

9.4/10 Exceptional! (1,985 reviews)

Room was very clean and comfortable

Reviewed on Feb 5, 2026

![Nalu Retreat & Nordic Spa](https://images.trvl-media.com/lodging/93000000/92730000/92723100/92723015/cb9766e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Nalu Retreat & Nordic Spa

$661

per person

Mar 23 - Mar 25

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

9.8/10 Exceptional! (28 reviews)

Everything was wonderful even through the cold snap in the weather. All details and instructions were clear and atmosphere was very cozy. Thanks!

Reviewed on Jan 25, 2026

![Brewery Park Hotel](https://images.trvl-media.com/lodging/89000000/88680000/88674600/88674565/3bd8bf7c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Brewery Park Hotel

North End

$529

per person

Mar 23 - Mar 25

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

9.2/10 Wonderful! (188 reviews)

Room was very clean, great space. Very quiet.

Reviewed on Feb 2, 2026

![HFX Airport Hotel](https://images.trvl-media.com/lodging/1000000/530000/528300/528264/8c5013ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### HFX Airport Hotel

$533

per person

Mar 23 - Mar 25

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

8.2/10 Very Good! (2,821 reviews)

Clean room, helpful staff, decent breakfast, good shuttle. Heater in the room was very noisy

Reviewed on Feb 6, 2026

## Find the Best Chester Vacation Packages

## Chester Essential Information

| Language        | English                                                                                                                                                                                                                                                                                                                                                                                   |
| --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
| Currency        | Canadian dollars                                                                                                                                                                                                                                                                                                                                                                          |
| Closest Airport | Stanfield Intl. Airport (YHZ)                                                                                                                                                                                                                                                                                                                                                             |
| Top Sights      | [Bayswater Beach Provincial Park](https://www.expedia.com/Bayswater-Beach-Provincial-Park-Bayswater.d6309731.Vacation-Attraction), [Graves Island Provincial Park](https://www.expedia.com/Graves-Island-Provincial-Park-East-Chester.d6309763.Vacation-Attraction) and [Saint Margarets Bay](https://www.expedia.com/Saint-Margarets-Bay-Canada.d553248635810193496.Vacation-Attraction) |

## Chester Hotel Deals

![Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia](https://images.trvl-media.com/lodging/54000000/53440000/53439100/53439075/88b54b4f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

 Hubbards NS

9.8/10 Exceptional! (98 reviews)

Great host and great property! You cannot beat the ocean views!

Reviewed on Sep 27, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=53439075&PinnedHotelID=53439075&HadPinnedHotel=true&regionId=553248635976006029)

[](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=53439075&PinnedHotelID=53439075&HadPinnedHotel=true&regionId=553248635976006029)

![Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring](https://images.trvl-media.com/lodging/92000000/91440000/91435200/91435158/cab845a5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

 Chester NS

9.6/10 Exceptional! (35 reviews)

Amazing overall!

Reviewed on Oct 30, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=91435158&PinnedHotelID=91435158&HadPinnedHotel=true&regionId=553248635976006029)

[](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=91435158&PinnedHotelID=91435158&HadPinnedHotel=true&regionId=553248635976006029)

![Cozy Oceanfront Escape with Hot Tub](https://images.trvl-media.com/lodging/101000000/100640000/100630800/100630749/eaca4f7a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cozy Oceanfront Escape with Hot Tub

 Chester NS

10/10 Exceptional! (24 reviews)

Host was cooperative and helped wih non scent environment

Reviewed on Feb 3, 2026

[Get rates](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=100630749&PinnedHotelID=100630749&HadPinnedHotel=true&regionId=553248635976006029)

[](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=100630749&PinnedHotelID=100630749&HadPinnedHotel=true&regionId=553248635976006029)

[See all 565 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&regionId=553248635976006029)

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.com/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.com/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)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

Explore a world of travel with Expedia

## Other vacations you might like

- Top cities in Chester
- Vacations and getaways similar to Chester
- Best vacation destinations by month

- [Chester Vacations ](https://expedia.com/Chester.d58468.Destination-Travel-Guides)
- [Western Shore Vacations ](https://expedia.com/Western-Shore.d181860.Destination-Travel-Guides)
- [Bayswater Vacations ](https://expedia.com/Bayswater.d6353709.Destination-Travel-Guides)
- [East River Point Vacations ](https://expedia.com/East-River-Point.d553248635977184223.Destination-Travel-Guides)
- [East River Vacations ](https://expedia.com/East-River.d3000475360.Destination-Travel-Guides)

- [Prince Edward Island Vacations ](https://expedia.com/Prince-Edward-Island.d6058122.Destination-Travel-Guides)
- [Quebec Vacations ](https://expedia.com/Quebec.d11183.Destination-Travel-Guides)
- [New Brunswick Vacations ](https://expedia.com/New-Brunswick.d11161.Destination-Travel-Guides)

- [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january)
- [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february)
- [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march)
- [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april)
- [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may)
- [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june)
- [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july)
- [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august)
- [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september)
- [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october)
- [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november)
- [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.