Title: Chester Vacation Packages & Trips 2026 from CA $292 | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx58468)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d58468.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d58468.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d58468.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d58468.Car-Rental-Guide) ![](https://images.trvl-media.com/place/58468/563e3b62-f804-4c09-b542-8c6504d90bff.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Chester Vacation Take the hassle out of travel planning with a Chester vacation package. A great neighborhood to base yourself in this captivating city is Garden Lots, which is good for watersports and much more. A trip to Chester is a superb opportunity to sightsee. Be sure to visit well-known attractions like [Oak Island](https://www.expedia.ca/Oak-Island-Nova-Scotia.d553248635976196878.Vacation-Attraction), [Tancook Island](https://www.expedia.ca/Tancook-Island-Chester.d553248621533087922.Vacation-Attraction) and [Chester Golf Club](https://www.expedia.ca/Chester-Golf-Club-Chester.d6301674.Vacation-Attraction). Stop dreaming and start traveling. Browse the wide range of options on Expedia today and finally put your Chester vacation plans into action! ## Top Chester Vacation Deals 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 CA $292 per person Feb 14 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Halifax (YHZ) 7.4/10 Good! (1,004 reviews) The staff was so helpful and friendly Reviewed on Dec 13, 2025 ![Inn on the Lake](https://images.trvl-media.com/lodging/1000000/60000/53000/52922/ac3a7a08_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn on the Lake CA $364 per person Feb 14 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Halifax (YHZ) 8.8/10 Excellent! (1,002 reviews) Unfortunately the power was off because of high winds so all food services for the evening were canceled. The room was clean and the bed very comfortable but we had a jacuzzi right next to the bed which was unexpected. It had a bit of a musty smell. The staff were outstanding though, very pleasant. Obviously the power situation was out of their control but it did come back on and our room was comfortable. Reviewed on Dec 21, 2025 ![The Hollis Halifax a DoubleTree Suites by Hilton Hotel](https://images.trvl-media.com/lodging/1000000/50000/41300/41224/b0c1515e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hollis Halifax a DoubleTree Suites by Hilton Hotel Downtown Halifax CA $544 per person Feb 27 - Mar 3 found 15 hours ago Roundtrip flight included Toronto (YTO) to Halifax (YHZ) 9/10 Wonderful! (647 reviews) Very happy with the amount of space in the suites, and the staff was very accommodating. Reviewed on Dec 6, 2025 ![Hampton Inn by Hilton Halifax Downtown](https://images.trvl-media.com/lodging/1000000/10000/2900/2808/d66b48c2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn by Hilton Halifax Downtown Downtown Halifax CA $658 per person Jan 28 - Jan 31 found 7 hours ago Roundtrip non-stop flight included Calgary (YYC) to Halifax (YHZ) 8.6/10 Excellent! (1,108 reviews) Very satisfied with this hotel Reviewed on Dec 16, 2025 ![Prince George Hotel](https://images.trvl-media.com/lodging/1000000/30000/22500/22435/5abe2c15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Prince George Hotel Downtown Halifax CA $416 per person Feb 14 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Halifax (YHZ) 9.4/10 Exceptional! (1,628 reviews) I celebrated my birthday at the Prince George. Everything was on point from the time we checked in at the reception desk until we checked out! I especially want to give a shout out to Kay, who ensured our stay was superb. Well done, Prince George. We will be back! :) Reviewed on Dec 20, 2025 ### Things to do in and around Chester Chester, Nova Scotia, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy golf vacations, explore nearby attractions, and relax on beautiful beaches. The town also features shopping centres and malls for those looking to browse local shops. With its charming city vibe, Chester is perfect for a memorable getaway filled with leisure and exploration. **Shopping** In Chester, you can shop at [Have A Yarn](https://www.expedia.ca/Have-A-Yarn.d553248621532865340.Vacation-Attraction) and [Northern Sun Gallery & Gifts](https://www.expedia.ca/Northern-Sun-Gallery-Gifts.d553248621532865341.Vacation-Attraction), both offering unique gifts and souvenirs. If you're up for a drive, visit [Bridgewater Mall](https://www.expedia.ca/Bridgewater-Mall.d6309475.Vacation-Attraction), located 29.0km away, where you'll find a variety of shops and entertainment options for the whole family. **Recreation** [Graves Island Provincial Park](https://www.expedia.ca/Graves-Island-Provincial-Park.d6309763.Vacation-Attraction) offers tranquil nature trails and scenic views, perfect for relaxation and rejuvenation. For a cultural experience, visit [Chester Playhouse](https://www.expedia.ca/Chester-Playhouse.d6301676.Vacation-Attraction), where you can enjoy captivating performances in a charming atmosphere. Additionally, the [Chester Golf Club](https://www.expedia.ca/Chester-Golf-Club.d6301674.Vacation-Attraction) invites you to unwind with a round of golf amidst beautiful outdoor settings. **Adventure** Hit the slopes at [Ski Martock](https://www.expedia.ca/Ski-Martock.d6089495.Vacation-Attraction), located 43.5km from Chester, where you can enjoy thrilling skiing experiences amidst stunning winter landscapes. For a different kind of excitement, visit [Ontree Fun and Adventure Park](https://www.expedia.ca/Ontree-Fun-And-Adventure-Park.d6301698.Vacation-Attraction), also 43.5km away, where you can zipline through the trees and conquer ropes courses in a beautiful outdoor setting. **Nightlife** Chester offers a charming nightlife with venues like the Chester Playhouse for live performances and the Kiwi Café for a relaxed bite and drink. For a lively atmosphere, enjoy the local music scene at the Rope Loft, where you can unwind by the water. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Chester Chester, Nova Scotia, is the perfect destination for outdoor enthusiasts and families alike, offering a blend of beautiful lakes, scenic islands, and inviting beaches. With a focus on beach and nature experiences, visitors can explore various attractions that highlight the area's stunning scenery. Whether you're seeking relaxation or adventure, Chester provides an array of activities to ensure a memorable vacation in this charming coastal town. - **[Oak Island: ](https://www.expedia.ca/Oak-Island.d553248635976196878.Vacation-Attraction)** Just 4.8km from Chester, Oak Island offers stunning beaches and a relaxed outdoor atmosphere. Explore the island's intriguing history and the legends that surround it, making it a perfect spot for nature lovers and adventure seekers alike. - **[Amicus Gallery: ](https://www.expedia.ca/Amicus-Gallery.d6301678.Vacation-Attraction)** Located in the heart of Chester, Amicus Gallery showcases local art and culture, providing a glimpse into the vibrant artistic community. Enjoy the diverse exhibitions and perhaps meet some of the artists behind the works. - **[St. Stephen's Church: ](https://www.expedia.ca/St-Stephens-Church.d553248621562269197.Vacation-Attraction)** This historic church in Chester is known for its beautiful architecture and serene atmosphere. Take a moment to appreciate the stunning stained glass windows and the rich history that this cherished community landmark represents. ### Best time to go to Chester The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in August, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in February, visitor numbers are average and weather is mostly with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.4°F (-2.0°C) | Light Rain | Mostly | Average | Slightly Low | | February | 27.5°F (-2.5°C) | Light Rain | Mostly | Average | Average | | March | 32.0°F (0.0°C) | Light Rain | Mostly | Average | Slightly Low | | April | 40.3°F (4.6°C) | Light Rain | Mostly | Average | Average | | May | 48.4°F (9.1°C) | Light Rain | Mostly | Average | Average | | June | 56.5°F (13.6°C) | Light Rain | Mostly Sunny | Average | Average | | July | 64.8°F (18.2°C) | Light Rain | Mostly Sunny | High | Slightly High | | August | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | High | Slightly High | | September | 61.3°F (16.3°C) | Light Rain | Mostly Sunny | High | Slightly High | | October | 52.5°F (11.4°C) | Light Rain | Mostly Sunny | Low | Average | | November | 43.0°F (6.1°C) | Light Rain | Mostly | Low | Average | | December | 34.9°F (1.6°C) | Light Rain | Mostly | Low | Slightly Low | ### Tips to save on your trip to Chester - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chester. - Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Chester. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Travelodge by Wyndham Bridgewater](https://images.trvl-media.com/lodging/1000000/20000/18000/17913/12a1f767_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Bridgewater 49 North St Bridgewater NS Fully refundableReserve now, pay when you stay CA $144 CA $174 total Jan 1 - Jan 2, 2026 includes taxes & fees 8/10 Very Good! (916 reviews) Room had all the necessities and was fresh and clean. Staff was very courteous and helpful. Enjoyed the breakfast. We plan to stay again. Reviewed on Dec 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=17913&PinnedHotelID=17913&HadPinnedHotel=true®ionId=58468) ![Best Western Plus Bridgewater Hotel & Convention Centre](https://images.trvl-media.com/lodging/4000000/3820000/3812400/3812334/c7642643_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Bridgewater Hotel & Convention Centre 527 Highway 10 Exit 12 Cookville NS Fully refundableReserve now, pay when you stay CA $150 CA $171 total Dec 28 - Dec 29 includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) Great stay. Clean room, friendly and helpful staff. Reviewed on Dec 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=3812334&PinnedHotelID=3812334&HadPinnedHotel=true®ionId=58468) ![Smugglers Cove Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517100/1517064/e53b71bd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Smugglers Cove Inn 139 Montague Street Lunenburg NS CA $169 CA $192 total Dec 23 - Dec 24 includes taxes & fees 8.8/10 Excellent! (765 reviews) Our go-to spot in Lunenburg! Great hospitality and amenities. The sushi restaurant that connects through the lobby next door is awesome! We’ll be back! Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F12%2F2025&endDate=24%2F12%2F2025&selected=1517064&PinnedHotelID=1517064&HadPinnedHotel=true®ionId=58468) [See all 305 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F12%2F2025&endDate=24%2F12%2F2025®ionId=58468) 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) ### Discover the most popular places to visit in Chester #### Chester Golf Club Enjoy a round of golf in Chester at Chester Golf Club. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants. [](https://expedia.ca/Chester-Golf-Club-Chester.d6301674.Vacation-Attraction) #### Lordly House Museum You can spend time studying the exhibits at Lordly House Museum during your trip to Chester. While in this family-friendly area, you can savor the top-notch restaurants. [](https://expedia.ca/Lordly-House-Museum-Chester.d6301680.Vacation-Attraction) #### Chester Playhouse You can enjoy a show at Chester Playhouse during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants. 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[Northern Sun Gallery & Gifts ](https://www.expedia.ca/Northern-Sun-Gallery-Gifts-Mahone-Bay.d553248621532865341.Vacation-Attraction) - [Oak Island ](https://www.expedia.ca/Oak-Island-Martins-Point.d553248635976196878.Vacation-Attraction) - [Queensland Beach Provincial Park ](https://www.expedia.ca/Queensland-Beach-Provincial-Park-Queensland.d6309727.Vacation-Attraction) - [Queensland Vacations ](https://www.expedia.ca/Queensland.d6069850.Destination-Travel-Guides) - [Shore Club Dance Hall ](https://www.expedia.ca/Shore-Club-Dance-Hall-Hubbards.d6309739.Vacation-Attraction) - [St John's Anglican Church ](https://www.expedia.ca/St-Johns-Anglican-Church-Lunenburg.d6300926.Vacation-Attraction) - [Swiss Air Flight 111 Memorial Bayswater ](https://www.expedia.ca/Swiss-Air-Flight-111-Memorial-Bayswater-Bayswater.d6309383.Vacation-Attraction) - [Tancook Islands Vacations ](https://www.expedia.ca/Tancook-Islands.d6351922.Destination-Travel-Guides) - [Western Shore Vacations ](https://www.expedia.ca/Western-Shore.d181860.Destination-Travel-Guides) - [Visit Western Shore ](https://www.expedia.ca/Western-Shore.dx181860) - [Budget Rental Cars in Western Shore ](https://www.expedia.ca/Budget-Car-Rentals-In-Western-Shore.d181860-c39.Car-Rental-Guide-Suppliers) - [Car rentals near Chester Golf Club ](https://www.expedia.ca/Car-Rentals-In-Chester-Golf-Club.d6301674.Car-Rental-Guide) - [Car rental Western Shore ](https://www.expedia.ca/Car-Rentals-In-Western-Shore.d181860.Car-Rental-Guide) - [Thrifty Car Rental Rental Cars in East River ](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-East-River.d3000475360-c45.Car-Rental-Guide-Suppliers) - [Gold River Vacation Rentals ](https://www.expedia.ca/Gold-River-Vacation-Rentals.d553248635977184228.Travel-Guide-VacationRentals) - [Western Shore Vacation Rentals ](https://www.expedia.ca/Western-Shore-Vacation-Rentals.d181860.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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