Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top vacation destinations in Chester
Chester
Western Shore
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse
CA $2,108
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.8/10 Exceptional! (8 reviews)
Everything was unique especially the automated system. Enjoyed the spa. We had some difficulty using the living room tv. Could not find local channels. Everything was LG channels. Otherwise the location, decor and amenities was extraordinary. We will tell our friends about this wonderful place.
Reviewed on Oct 5, 2026
Chester Hotel Deals
Oak Island Resort & Conference Centre
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
CA $145
CA $165 total
Nov 11 - Nov 12
includes taxes & fees
8.4/10 Very good! (626 reviews)
"great place to stay"
Reviewed on Oct 16, 2026
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Chester NS
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore NS
CA $290
CA $506 total
Oct 20 - Oct 21
includes taxes & fees
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.
Frequently asked questions
How much does a Chester vacation package cost?
Starting from just CA $793, a vacation package is your ticket to inexpensive travel. Customize your Chester adventure by selecting from our comprehensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Chester?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we've got it all. Select the combination that best suits you and watch your savings grow. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotel options globally, which lets you customize your Chester vacation.
What are the top hotels in Chester?
For properties in Deep Cove with cozy beds and friendly service, you can't go past Oak Island Resort & Conference Centre and On The Beautiful South Shore Near Chester And Hubbards. If you're stopping by Fox Point as well, you can look forward to a relaxing night's sleep at Rya - 2023 - 24 - 03281153042804049 or Oceanfront Family Cottage - 5mins From Beach.
How far in advance should I book my Chester vacation?
While prices fluctuate, we generally advise booking your seats as soon as possible. Many international airfares can be found on Expedia up to 12 months in advance. If you're booking last minute, you might still be in luck. Discount prices to Chester occasionally appear just weeks before departure.
What does an Expedia Chester travel package include?
Hotels, flights and car rentals — we bring you all the best deals. All you have to do is pick and choose your ideal combination. Once you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to craft an unforgettable Chester getaway.
What should I know before booking a Chester travel package?
When you book your hotels, flights and car rentals together, you'll nab awesome discounts. Whether you're planning a mountain getaway in a cabin or prefer to stay in a comfortable hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Chester Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply choose the carrier that suits you and create your ideal Chester escape.
If I'm not able to travel, can I cancel my Chester vacation package?
It is possible to cancel your Chester booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
Stay near popular Chester attractions
Bayswater Beach Provincial Park
9.0/10 (26 reviews)
If a restful vacation is part of your travel plans, Bayswater Beach Provincial Park might be the perfect place to seek out during your trip to Bayswater. Make some time to visit the monuments while you're in the area.
Oak Island
9.0/10 (95 reviews)
Commune with nature and explore the great outdoors at Oak Island during your travels in Martins Point.
Chester Golf Club
8.4/10 (28 reviews)
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.
Chester Playhouse
8.6/10 (12 reviews)
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.
Black Island
Commune with nature and explore the great outdoors at Black Island during your travels in Aspotogan.
Graves Island Provincial Park
8.6/10 (9 reviews)
Commune with nature and explore the great outdoors at Graves Island Provincial Park during your travels in East Chester. Stroll along the seaside or experience the entertainment venues in this family-friendly area.
Swiss Air Flight 111 Memorial Bayswater
9.0/10 (59 reviews)
You can learn about the history of Bayswater when you stop by Swiss Air Flight 111 Memorial Bayswater. Stroll along the seaside or experience the entertainment venues in this family-friendly area.
What to do in Chester
Halifax Small Group Peggy’s Cove Driving Tour
CA $79
per adult
96% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
CA $175
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
