Chester Vacation Packages

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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, Tancook Island and Chester Golf Club. 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.
Windmill walk

Windmill walk

3 out of 5
Harbourview
per person
Aug. 5 - Aug. 9
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.2/10 Wonderful! (107 reviews)
Perfect for a couple, home away from home. Safe clean, easy access to highway. Grocery store near by . Thank you Andy !

Reviewed on Apr. 29, 2024

The Halliburton

The Halliburton

3.5 out of 5
Downtown Halifax
per person
Aug. 5 - Aug. 9
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (1,008 reviews)
not updated but clean and charming a bit dated.

Reviewed on May 18, 2024

Prince George Hotel

Prince George Hotel

4 out of 5
Downtown Halifax
per person
Jul. 27 - Aug. 2
Roundtrip non-stop flight included
Edmonton (YEG) to Halifax (YHZ)
9.2/10 Wonderful! (1,359 reviews)
Parking garage is a bit tight with all the huge vehicles people drive now .

Reviewed on May 19, 2024

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
per person
Jul. 27 - Aug. 2
Roundtrip non-stop flight included
Edmonton (YEG) to Halifax (YHZ)
9/10 Wonderful! (1,580 reviews)
Safe in the room, but when called the desk they said no access to it and pretty much hung up. Lobby washrooms early morning women’s had no Kleenex and men’s had no toilet paper. Yes, the guy in the desk took care of asap, but it makes you wonder how often they’re cleaned and restocked.

Reviewed on May 17, 2024

Hotel Halifax

Hotel Halifax

3.5 out of 5
Downtown Halifax
per person
Jul. 27 - Aug. 2
Roundtrip non-stop flight included
Edmonton (YEG) to Halifax (YHZ)
8.2/10 Very Good! (3,584 reviews)
Great location to explore Halifax. Lots of construction in the neighborhood.

Reviewed on May 19, 2024

Chester Hotel Deals

Best Western Plus Bridgewater Hotel & Convention Centre
Best Western Plus Bridgewater Hotel & Convention Centre
3.5 out of 5
527 Highway 10 Exit 12, Cookville, NS
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 28 to May 29
CA $167
CA $192 total
includes taxes & fees
May 28 - May 29
9.2/10 Wonderful! (740 reviews)
"Under construction, so breakfast was lacking."

Reviewed on May 9, 2024

Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn
Smugglers Cove Inn
4 out of 5
139 Montague Street, Lunenburg, NS
The price is CA $186 per night from May 26 to May 27
CA $186
CA $214 total
includes taxes & fees
May 26 - May 27
8.8/10 Excellent! (486 reviews)
Very well situated.
"Very well positioned for the waterfront and restaurants. Kind and helpful management and staff."

Reviewed on May 1, 2024

Smugglers Cove Inn
Rum Runner Inn
Rum Runner Inn
4 out of 5
66 Montague Street, Lunenburg, NS
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from May 20 to May 21
CA $149
CA $171 total
includes taxes & fees
May 20 - May 21
8.8/10 Excellent! (761 reviews)
"We arrived there before noon and we needed to use the bathroom. As our room was not ready yet, they did let us use the bathroom of the cleaned room. They said they wouldn’t mind cleaning its bathroom again. They were so friendly and helpful. The view of the harbour from our toom was great."

Reviewed on May 8, 2024

Rum Runner Inn
See all 265 properties in Chester
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Chester from just CA $615. And the more you bundle, the more money you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Chester?
Creating your own Chester vacation package with Expedia is such a simple way to save. We have more than 550 air carriers and 1,000,000 hotels globally. With such a fantastic range to choose from, you’ll have no difficulty putting together your ideal vacation.
Where should I stay in Chester?
A vacation in Chester isn’t complete without seeing Chester Golf Club, Tancook Island and Graves Island Provincial Park. Spend your evenings near these tourist attractions and make sightseeing simple.
What are the top hotels in Chester?
When it comes to welcoming places to stay in Chester, you can’t go past Family Cottage In The Village Of Chester Ns. Have a look at our deals and score a bargain.
How far in advance should I book my Chester vacation?
While prices do change, we generally advise booking your seats as early as possible. Many international fares are available on Expedia up to 12 months in advance. If you’re booking late, you might still get lucky. Low prices to Chester sometimes emerge only weeks before departure.
What does an Expedia Chester travel package include?
Packages include hotels, flights and rental cars, but you can mix and match them to create your dream Chester getaway. You can also add on fun things like activities and experiences once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll score discounts you won’t find elsewhere.
What should I know before booking a Chester travel package?
When you book your hotels, flights and car rentals together, you’ll be rewarded with awesome discounts. Whether you’re organizing an island getaway in a villa or want to stay in a cozy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Chester Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Chester vacation package?
Whether it’s your hotel, flight or rental car, you can cancel or amend it. Locked in your Chester vacation package in the last 24 hours? You may be able to make changes for free. For older bookings, you may incur a fee from your airline, hotel or car rental company. For more details, look up our Customer Service Portal. We’ll help you each step of the way.

Discover the most popular places to visit in Chester

Image for Chester Golf Club

Chester Golf Club

4/5(12 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 Golf Club
Image for Tancook Island

Tancook Island

Find out about the history of Chester with a stop at Tancook Island. While in this family-friendly area, you can savor the top-notch restaurants.

Tancook Island
Image for Chester Playhouse

Chester Playhouse

4.5/5(6 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 Playhouse

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