Chester Vacation Packages

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Top vacation destinations in Chester

Chester which includes a house and a small town or village
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Chester

Chester

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (665 reviews)
The room was immaculate. The staff were pleasant. The breakfast was far superior to the usual hotel fare. The facility, although serviceable, is old.

Reviewed on Aug. 12, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on Jul. 25, 2025

Liscombe Lodge Resort and Conference Centre

Liscombe Lodge Resort and Conference Centre

2.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (259 reviews)
This is a fabulous lodge of the variety rarely seen anymore, offering personal service, a great onsite restaurant, and lots of included amenities, all on a picturesque riverfront setting. It is not a new property, made in a cookie cutter variety or modern design! If you can only enjoy those sort of places, stay away! But otherwise, you will be delighted, we were!

Reviewed on Aug. 9, 2025

Moxy Halifax Downtown

Moxy Halifax Downtown

3.5 out of 5
Downtown Halifax
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9/10 Wonderful! (683 reviews)
Brand new property. Right downtown. 15 mins from the boardwalk.

Reviewed on Aug. 14, 2025

Holiday Inn Express & Suites Halifax Airport by IHG

Holiday Inn Express & Suites Halifax Airport by IHG

2.5 out of 5
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.8/10 Excellent! (2,188 reviews)
The bed and pillows were extremely comfortable. We appreciated the extra blankets. The breakfast buffet was excellent.

Reviewed on Aug. 14, 2025

Chester Hotel Deals

Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

Hubbards
9.8/10 Exceptional! (47 reviews)
Best VRBO EVER!!!
"Everything was perfect from location to the hosts!!The hosts were actually more than great, they became friends.You couldn’t ask for more attentive people"

Reviewed on Aug. 12, 2025

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Ocean front cottage in the heart of Hubbards.
Moonlight Cottage

Moonlight Cottage

Hubbards
9.6/10 Exceptional! (11 reviews)
"It was beautiful and scenic, relaxing, and fun with the ping pong table, affordable for the family and the owners were accommodating"

Reviewed on Jul. 23, 2025

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Moonlight Cottage
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
133 Kearney Lake Rd, Halifax, NS
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Sep 1 to Sep 2
CA $219
CA $257 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,980 reviews)
"It was very quiet and clean"

Reviewed on Aug. 11, 2025

Chateau Bedford, Trademark Collection by Wyndham
See all 535 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 $530, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.