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.
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was CA $572, price is now CA $495 per person
CA $495
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.2/10 Wonderful! (2,340 reviews)
Breakfast was excellent, the room was clean, water pressure in the shower was excellent but when we went for a swim the pool was too cold to enjoy.

Reviewed on Oct 27, 2026

Brewery Park Hotel

Brewery Park Hotel

3.5 out of 5
North End
Price was CA $670, price is now CA $527 per person
CA $527
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (292 reviews)
This was a very nice apartment hotel, close to downtown and with a cute cafe located right downstairs. I will warn for those needing overnight parking, check the street signs as not all streets allow overnight parking on certain nights. When parking get filled in front of and on the side streets, it can be difficult to find a spot. Would recommend to travel light as there is no elevator. The room was spacious and nice with lots of sunlight coming in. Would recommend for sure

Reviewed on Oct 24, 2026

Red George Inn and Suites

Red George Inn and Suites

2 out of 5
Downtown Halifax
Price was CA $623, price is now CA $521 per person
CA $521
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (213 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 $1,238, price is now CA $1,050 per person
CA $1,050
per person
Jan 15 - Jan 18
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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was CA $568, price is now CA $497 per person
CA $497
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
7.2/10 Good! (1,320 reviews)
The people next door had a dog and were loud. The staff were wonderful.

Reviewed on Oct 26, 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 $149 per night from Nov 8 to Nov 9
CA $149
CA $169 total
Nov 8 - Nov 9
includes taxes & fees
8.4/10 Very good! (634 reviews)
"Room was very clean and excellent staff. They served a delicious breakfast and we enjoyed the live entertainment and amenities! We will return"

Reviewed on Oct 26, 2026

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 622 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.
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Frequently asked questions

How much does a Chester vacation package cost?
Starting from just CA $495, 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

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
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
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.