Chester Vacation Packages

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Top vacation destinations in Chester

A large, two-story house with a steeply pitched roof and a chimney.
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Chester

Chester
A white and red lighthouse with a clear blue sky in the background.
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Western Shore

Western Shore

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Brewery Park Hotel

Brewery Park Hotel

3.5 out of 5
North End
Price was CA $1,224, price is now CA $679 per person
CA $679
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (292 reviews)

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Price was CA $2,594, price is now CA $1,802 per person
CA $1,802
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.8/10 Exceptional! (9 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

Red George Inn and Suites

Red George Inn and Suites

2 out of 5
Downtown Halifax
Price was CA $1,230, price is now CA $866 per person
CA $866
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (213 reviews)
Great stay, owners were very nice, would stay again

Reviewed on Nov 4, 2026

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was CA $1,092, price is now CA $786 per person
CA $786
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
7.2/10 Good! (1,320 reviews)

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was CA $1,041, price is now CA $780 per person
CA $780
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.2/10 Wonderful! (2,340 reviews)
It was so clean and the staff was very nice and accommodating

Reviewed on Nov 5, 2026

Chester Hotel Deals

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 11 to Nov 12
CA $150
CA $171 total
Nov 11 - Nov 12
includes taxes & fees
Oak Island Resort & Conference Centre
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Chester NS
9.8/10 Exceptional! (52 reviews)
"Great place on the ocean. We had cool weather so a patio heater would b a great addition."

Reviewed on Oct 26, 2026

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Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

Hubbards NS
9.8/10 Exceptional! (74 reviews)
"We loved the cottage and its convenient location for all our excursions on the south shore. It was cozy, clean and quiet. The mattress was really comfortable. We would definitely stay again."

Reviewed on Oct 12, 2026

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Ocean front cottage in the heart of Hubbards.
See all 646 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Chester vacation package cost?
Starting from just CA $679, 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.
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What to do in Chester

Lunenburg from Bluenose Golf Course

Half-Day Small-Group Tour of Nova Scotia's South Shore

CA $175
per adult
100% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
Halifax Small Group Peggy’s Cove Driving Tour

Halifax Small Group Peggy’s Cove Driving Tour

CA $88
per adult
96% of travellers recommend
Halifax Small Group Peggy’s Cove Driving Tour
Peggys Cove Sunset Tour

Peggys Cove Sunset Tour

CA $106
per adult
Peggys Cove Sunset Tour
See all activities in Chester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.