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.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
Save 100% on your flight
per person
Sep 25 - Oct 1
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (620 reviews)
We stayed just one night It was raining but we were confortable and it was clean

Reviewed on Jul. 11, 2025

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.6/10 Exceptional! (1,695 reviews)
Wonderful stay here on the 12th floor with views overlooking the citadel. Would recommend and stay again if I ever find myself back in Halifax!

Reviewed on Jul. 7, 2025

Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

2 out of 5
Save 100% on your flight
per person
Sep 25 - Oct 1
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.4/10 Very Good! (1,008 reviews)
I lost my engagement ring & didn’t realize until hours after checkout. I was multiple places but i started my search with the hotel. They were able to locate it within very tense for me moments & return it. I so appreciate their help!! The staff were fabulous during my stay. The only negative I have to report is that I was expecting boiled eggs in the continental breakfast & that was a no go.

Reviewed on Jul. 7, 2025

Liscombe Lodge Resort and Conference Centre

Liscombe Lodge Resort and Conference Centre

2.5 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (237 reviews)
I’ve been coming to the lodge for 30 yrs, the chalets and cabins are looking tired and it’s a large property to keep on top of

Reviewed on Jun. 30, 2025

Cambridge Suites Hotel

Cambridge Suites Hotel

3 out of 5
Downtown Halifax
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9/10 Wonderful! (1,967 reviews)
Hotel is ok, tired average decor. Overpriced for the standard of the rooms. Friendly enough staff, good location.

Reviewed on Jul. 12, 2025

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Chester Hotel Deals

Family Home In the Heart of the Village of Chester
Family Home In the Heart of the Village of Chester
Chester
9.4/10 Exceptional! (21 reviews)
Awesome Ladies Getaway
"Such a spacious home for our ladies getaway. Loved the little extras, like a variety of Starbucks pods. Lots of seating inside and out. Just a short visually beautiful walk to cafe's, pubs and shops. We will certainly be back!"

Reviewed on Jun. 23, 2025

Get rates
Family Home In the Heart of the Village of Chester
Travelodge by Wyndham Bridgewater
Travelodge by Wyndham Bridgewater
2 out of 5
49 North St, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Jul 14 to Jul 15
CA $185
CA $224 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very Good! (717 reviews)
"Location is great Friendly staff"

Reviewed on Jul. 6, 2025

Travelodge by Wyndham Bridgewater
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
The price is CA $238 per night from Jul 19 to Jul 20
CA $238
CA $271 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (892 reviews)
"We had a good time, restaurant is very nice - lots of veg options."

Reviewed on Jul. 1, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
See all 272 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

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Chester

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

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

Lordly House Museum

5/5(1 review)

You can spend time studying the exhibits at Lordly House Museum during your trip to Chester. While in this family-friendly area, you can savor the top-notch restaurants.

Lordly House Museum

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this destination from CA $527 on Expedia. But how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
The off-season is the best time to head to Chester if you're trying to save. Another tip for getting cheap Chester vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Chester?
For your Chester vacation, a handful of days will be enough to see the top spots. Be sure to stop by Tancook Island --- it's one of the most popular sights in this destination. If you want more adventure, think about basing yourself here and setting off on some trips from Chester.
Is it worth booking a vacation package to Chester?
Boasting a host of highlights starting with its amazing watersports, Chester is a good vacation destination. Whether you'd like to visit attractions such as Chester Golf Club and Tancook Island or venture off the beaten track, you'll have loads to keep you busy during your Chester vacation.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Chester package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester getaway off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chester?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Chester escape.
How to plan a trip to Chester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite season and the available activities will also help you decide when to escape to Chester.
  2. Set your budget: Consider expenses like flights, transportation and food when calculating how much to set aside for your trip to Chester. Then, pick a property that works with your budget, whether that's an economical stay or a swankier retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chester, you can figure out the right length of your break. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.

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