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.
Cambridge Suites Hotel

Cambridge Suites Hotel

3 out of 5
Downtown Halifax
per person
Jun. 23 - Jun. 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9/10 Wonderful! (1,795 reviews)
The staff are very friendly and helpful

Reviewed on Apr. 28, 2025

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
Save 100% on your flight
per person
Jul. 9 - Jul. 16
found 7 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (1,611 reviews)
Staff, the overall beauty of the building inside and out. Restaurant is top notc, rooms are amazing and OHhe pillows!!

Reviewed on Apr. 28, 2025

Prince George Hotel

Prince George Hotel

4 out of 5
Downtown Halifax
Save 100% on your flight
per person
Jun. 23 - Jun. 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (1,399 reviews)
LOVE where the Prince George is located and that I can walk anywhere downtown. Great service checking in ... couldn't ask for better!

Reviewed on Apr. 29, 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
per person
Jul. 5 - Jul. 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
7.8/10 Good! (4,119 reviews)
The perfect spot for a downtown stay in Halifax. The Barrington Hotel is close to the waterfront and all of the amazing restaurants, shops and sights to see along the boardwalk. We had a fabulous stay and would highly recommend it for solo and family stays.

Reviewed on Apr. 29, 2025

Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

3 out of 5
per person
Jul. 5 - Jul. 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (1,083 reviews)
We had an amazing stay celebrating my daughter's 10th birthday.

Reviewed on Apr. 28, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Family Cottage in the Village of Chester NS - 5 Bedrooms
Family Cottage in the Village of Chester NS - 5 Bedrooms
Chester, NS
9.4/10 Exceptional! (20 reviews)
Great Spot
"Awesome time!"

Reviewed on Oct. 22, 2023

Get rates
Family Cottage in the Village of Chester NS - 5 Bedrooms
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 $166 per night from May 19 to May 20
CA $166
CA $190 total
includes taxes & fees
May 19 - May 20
9.2/10 Wonderful! (847 reviews)
"Great place for families"

Reviewed on Apr. 27, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Days Inn & Conference Center by Wyndham Bridgewater
Days Inn & Conference Center by Wyndham Bridgewater
2.5 out of 5
50 North Street, Hwy 103 and North Street, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 4 to May 5
CA $118
CA $135 total
includes taxes & fees
May 4 - May 5
7.4/10 Good! (1,001 reviews)
"great place to stay very quiet"

Reviewed on Apr. 27, 2025

Days Inn & Conference Center by Wyndham Bridgewater
See all 254 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

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this destination from CA $776 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.

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