Title: Chester Vacation Packages & Trips 2026 from CA $746 | 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. ![Super 8 by Wyndham Windsor NS](https://images.trvl-media.com/lodging/2000000/1720000/1711000/1710981/dc71ef36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Windsor NS CA $746 per person Mar 24 - Mar 28 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Halifax (YHZ) 8.6/10 Excellent! (1,000 reviews) Room was very clean and excellent service from the staff. Reviewed on Jan 13, 2026 ![Digby Pines Golf Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/890100/890065/5913a6d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Digby Pines Golf Resort and Spa CA $748 per person Mar 24 - Mar 28 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Halifax (YHZ) 8/10 Very Good! (1,040 reviews) the staff are extremely friendly and helpful. Reviewed on Jan 15, 2026 ![White Point Beach Resort](https://images.trvl-media.com/lodging/102000000/101270000/101260600/101260598/4485bc3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### White Point Beach Resort CA $985 per person Mar 24 - Mar 28 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Halifax (YHZ) 9/10 Wonderful! (113 reviews) Amazing place, it’s always a great day at White Point! Reviewed on Dec 21, 2025 ![Cambridge Suites Hotel](https://images.trvl-media.com/lodging/1000000/10000/2900/2858/2fb85b9d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cambridge Suites Hotel Downtown Halifax CA $1,100 per person Apr 1 - Apr 8 found 1 day ago Roundtrip flight included Ottawa (YOW) to Halifax (YHZ) 9/10 Wonderful! (2,239 reviews) Fantastic rooms, staff and breakfast in the morning! Reviewed on Jan 13, 2026 ![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 $1,058 per person Apr 1 - Apr 8 found 1 day ago Roundtrip flight included Ottawa (YOW) to Halifax (YHZ) 8.6/10 Excellent! (1,108 reviews) Was good just no parking Reviewed on Jan 13, 2026 ### Things to do in and around Chester Chester, Nova Scotia, is perfect for outdoor family vacations, featuring a scenic boardwalk and excellent golf courses. Visitors can enjoy memorable golf vacations, explore nearby attractions, and indulge in beach activities. The charming shops provide a delightful browsing experience, making Chester a wonderful destination for those seeking relaxation and adventure in a picturesque coastal setting. **Shopping** In Chester, you can visit [Northern Sun Gallery & Gifts](https://www.expedia.ca/Northern-Sun-Gallery-Gifts-Mahone-Bay.d553248621532865341.Vacation-Attraction) for unique items. If you're up for a drive, the Hubbards Farmer's Market offers local produce and crafts, while the [Bridgewater Mall](https://www.expedia.ca/Bridgewater-Mall-Bridgewater.d6309475.Vacation-Attraction) features a variety of shops and entertainment, located 29.0km away. Enjoy your shopping adventure. **Recreation** At [Graves Island Provincial Park](https://www.expedia.ca/Graves-Island-Provincial-Park-East-Chester.d6309763.Vacation-Attraction), immerse yourself in nature's tranquility, enjoying serene walks and beautiful views. Meanwhile, the [Chester Playhouse](https://www.expedia.ca/Chester-Playhouse-Chester.d6301676.Vacation-Attraction) offers a delightful cultural experience with engaging performances, perfect for a family night out. For sports enthusiasts, the [Chester Golf Club](https://www.expedia.ca/Chester-Golf-Club-Chester.d6301674.Vacation-Attraction) provides an invigorating outdoor atmosphere with stunning landscapes. **Adventure** Experience the thrills of [Ski Martock](https://www.expedia.ca/Ski-Martock-Windsor-Forks.d6089495.Vacation-Attraction), a ski field 43.5km from Chester, where you can enjoy skiing and embrace the sporty atmosphere. For an exhilarating adventure, head to [Ontree Fun and Adventure Park](https://www.expedia.ca/Ontree-Fun-And-Adventure-Park-Windsor-Forks.d6301698.Vacation-Attraction), also 43.5km away, offering a fantastic zipline and ropes course surrounded by nature. **Nightlife** Chester offers a charming nightlife with cozy spots like the Chester Playhouse for local performances and the Kiwi Café for a laid-back meal. For a lively evening, enjoy a drink at the nearby Oceanstone Seaside Resort, where you can soak in the coastal ambiance under the stars. \*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 an ideal destination for families seeking outdoor and beach vacations. With its picturesque lakes, charming islands, and beautiful beaches, visitors can enjoy a variety of scenic experiences. Explore top attractions that highlight the area's natural beauty, perfect for those looking to relax by the water or engage in outdoor activities. Whether you're with family or friends, Chester offers a delightful getaway filled with adventure and tranquility. - **[Oak Island: ](https://www.expedia.ca/Oak-Island-Martins-Point.d553248635976196878.Vacation-Attraction)** A short 4.8km journey from Chester, Oak Island offers stunning beaches and an inviting outdoor atmosphere. Explore the intriguing legends surrounding the island, including the famous treasure hunt that has captivated adventurers for centuries. - **[Lordly House Museum: ](https://www.expedia.ca/Lordly-House-Museum-Chester.d6301680.Vacation-Attraction)** Located in the heart of Chester, this museum showcases the rich cultural history of the area. Wander through its exhibits to gain insight into the local heritage and enjoy the charming architecture of this historic site. - **[Bayswater Beach Provincial Park: ](https://www.expedia.ca/Bayswater-Beach-Provincial-Park-Bayswater.d6309731.Vacation-Attraction)** Situated 14.5km from Chester, this picturesque beach park provides a serene escape with beautiful sandy shores and tranquil waters, perfect for a relaxing day by the sea. ### 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 cloudy 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 Cloudy | Average | Slightly Low | | February | 27.5°F (-2.5°C) | Light Rain | Mostly Cloudy | Average | Average | | March | 32.0°F (0.0°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 40.3°F (4.6°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 48.4°F (9.1°C) | Light Rain | Mostly Cloudy | 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 Cloudy | Low | Average | | December | 34.9°F (1.6°C) | Light Rain | Mostly Cloudy | Low | Slightly Low | ### Tips to save on your trip to Chester - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - 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 ![Family Home In the Heart of the Village of Chester](https://images.trvl-media.com/lodging/35000000/34340000/34338200/34338116/72d8aa3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Family Home In the Heart of the Village of Chester Chester NS 9.4/10 Exceptional! (24 reviews) Chester Nova Scotia This is a great whole home property that offers a lot of easy trip options. There is a super cute small downtown that is a good spot for breakfast / shopping. There is a grocery store super close to the house and the kitchen is well equipped for any meal. The home has no AC but did provide fans. ... Reviewed on Jul 6, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=34338116&PinnedHotelID=34338116&HadPinnedHotel=true®ionId=58468) [](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=34338116&PinnedHotelID=34338116&HadPinnedHotel=true®ionId=58468) ![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 $130 CA $157 total Jan 18 - Jan 19 includes taxes & fees 8/10 Very Good! (917 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=18%2F01%2F2026&endDate=19%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 $158 CA $181 total Jan 25 - Jan 26 includes taxes & fees 9.2/10 Wonderful! (1,003 reviews) Friendly staff, great restaurant Reviewed on Jan 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=3812334&PinnedHotelID=3812334&HadPinnedHotel=true®ionId=58468) [See all 298 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®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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[Chester Playhouse ](https://www.expedia.ca/Chester-Playhouse-Chester.d6301676.Vacation-Attraction) - [Cocoa Organic Spa & Boutique ](https://www.expedia.ca/Cocoa-Organic-Spa-Boutique-Mahone-Bay.d553248621532865346.Vacation-Attraction) - [Fisheries Museum of the Atlantic ](https://www.expedia.ca/Fisheries-Museum-Of-The-Atlantic-Lunenburg.d6281565.Vacation-Attraction) - [Visit Gold River ](https://www.expedia.ca/Gold-River.dx553248635977184228) - [Graves Island Provincial Park ](https://www.expedia.ca/Graves-Island-Provincial-Park-East-Chester.d6309763.Vacation-Attraction) - [Halifax and Southwestern Railway Museum ](https://www.expedia.ca/Halifax-And-Southwestern-Railway-Museum-Centre.d6279979.Vacation-Attraction) - [Heckman-Morash House ](https://www.expedia.ca/Heckman-Morash-House-Lunenburg.d6309380.Vacation-Attraction) - [Hubbards Beach ](https://www.expedia.ca/Hubbards-Beach-Hubbards.d6309737.Vacation-Attraction) - [Hubbards Vacations ](https://www.expedia.ca/Hubbards.d717290204834050048.Destination-Travel-Guides) - [Lunenburg Art Gallery ](https://www.expedia.ca/Lunenburg-Art-Gallery-Lunenburg.d6301370.Vacation-Attraction) - [Lunenburg County Vacations ](https://www.expedia.ca/Lunenburg-County.d553248635976434171.Destination-Travel-Guides) - [Lunenburg Opera House ](https://www.expedia.ca/Lunenburg-Opera-House-Lunenburg.d553248621533089743.Vacation-Attraction) - [Lunenburg Visitor Information Centre ](https://www.expedia.ca/Lunenburg-Visitor-Information-Centre-Lunenburg.d553248621563221020.Vacation-Attraction) - [Lunenburg Waterfront Vacations ](https://www.expedia.ca/Lunenburg-Waterfront.d6309813.Destination-Travel-Guides) - [Lunenburg Vacations ](https://www.expedia.ca/Lunenburg.d6058263.Destination-Travel-Guides) - [Mahone Bay Swimming Pool ](https://www.expedia.ca/Mahone-Bay-Swimming-Pool-Mahone-Bay.d6301694.Vacation-Attraction) - [Mahone Bay Vacations ](https://www.expedia.ca/Mahone-Bay.d181853.Destination-Travel-Guides) - [Mill Cove Vacations ](https://www.expedia.ca/Mill-Cove.d6294394.Destination-Travel-Guides) - [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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