Chester Vacation Packages
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Top vacation destinations in Chester
Chester
Western Shore
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
CA $436
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
7.2/10 Good! (1,288 reviews)
Price was right, room was fine but the hotel along with our room was stifling hot. The room AC could not keep up, though it was only 17c outside. Needless to say, not a great nights sleep.
Reviewed on Oct 1, 2026
Burgundy Dream Bed and Breakfast
CA $461
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.8/10 Exceptional! (159 reviews)
We enjoyed our stay very much! This place has so much to offer besides accomodation: access to the lake, table tennis, great breakfast with superpleasant hosts, laundry facilities, would deer occasionally visiting the front lawn ... If we are in Halifax again we'll definitely be back.
Reviewed on Sep 30, 2026
Chester Hotel Deals
Oak Island Resort & Conference Centre
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
CA $163
CA $186 total
Nov 1 - Nov 2
includes taxes & fees
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Chester NS
9.8/10 Exceptional! (48 reviews)
"Quiet and relaxing. Very thoughtful touches in each room. Waterfall shower is soothing. Would stay here again."
Reviewed on Sep 19, 2026
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore NS
CA $390
CA $640 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (27 reviews)
"When something is listed as a bedroom, I’m expecting a separate room with a prepared bed, not a fold down futon or pull out sofa bed. Otherwise the location, view and cleanliness was outstanding."
Reviewed on Sep 23, 2026
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 $436, 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.
Chester Art Center
8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chester Art Center during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.
St. Stephen's Church
9.2/10 (11 reviews)
After visiting St. Stephen's Church, make a plan to see the other sights and activities in Chester. Amble around this family-friendly area's waterfront or experience its entertainment venues.
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.
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.
