Chester Vacation Packages 2025/2026 from $232

Chester flight + hotel vacation packages

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

The Barrington Hotel

Downtown Halifax

$232

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the sauna, bar/lounge, and snack bar/deli.

Lux Exec Home HFX Waterfront Pool Hot Tub

Save 100% on your flight

$720

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. A seasonal outdoor pool and laundry facilities are also provided.

Sandman Signature Dartmouth Hotel & Suites

Save 100% on your flight

$328

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and luggage storage are also offered on site.

Cambridge Suites Hotel

Downtown Halifax

Save 100% on your flight

$310

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the a rooftop terrace and free on-the-go breakfast each morning.

Holiday Inn Express & Suites Halifax Airport by IHG

Save 100% on your flight

$307

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.

Top Chester hotels deals

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12, Cookville, NS

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$195 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Days Inn & Conference Center by Wyndham Bridgewater

50 North Street, Hwy 103 and North Street, Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$164 total

Oct 2 - Oct 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Parking included

Bridgewater Hotel

35 High St., Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$101 total

Oct 16 - Oct 17

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, laundry facilities, and free newspapers are also on offer.

Pet friendly

Parking included

Travelodge by Wyndham Bridgewater

49 North St, Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$161 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free on-the-go breakfast each morning. Express check-out is provided and the front desk is staffed around-the-clock.

Breakfast included

Pet friendly

Surfside Inn

9609 St Margaret's Bay Rd., Queensland, NS

$187 nightly

$220 total

Sep 28 - Sep 29

Total with taxes and fees

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and express check-out are also provided.

Parking included

Free WiFi

Miller House By the Bay

624 Main street, mahone bay, NS

$101 nightly

$116 total

Oct 1 - Oct 2

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and a library are also on offer.

Parking included

Free WiFi

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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.

Popular places to visit

Tancook Island

Find out about the history of Chester with a stop at Tancook Island. While in this family-friendly area, you can savor the top-notch restaurants.

Chester Golf Club

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 Playhouse

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.

Frequently asked questions

How much are vacation packages to Chester?

With deals starting at just $232, hotel and flight packages are a great way to stretch your vacation budget. Chester, here you come!

Where can I get the best vacation package deals for Chester?

Travelocity is the only place you need to go to score a great Chester package deal. Select from as many as 400 airlines and 1,000,000 properties worldwide and craft a vacation package that suits your style. With so many options at hand, it's easy to plan your next great escape.

Why should I book my Chester vacation package with Travelocity?

The three S's — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.

Can I save money on my Chester car rental if I bundle it with my hotel or flight?

Combining your bookings into a Chester vacation package will save you some serious money. Choose a flight and car; a flight, car and hotel; or a car and hotel. You won't find a better way to explore the greater Chester area than with your own set of wheels. You can also add experiences and tours to your Travelocity package.

What is there to do in Chester?

Chester is full of sights to discover, like Chester Golf Club and Tancook Island. These two popular attractions top most travelers' must-see lists.

Where should I stay when visiting Chester?

If you're after someplace comfortable to base yourself, have a look at the 1800' | Front HBR | DT 5 Min Walk | Water views. It's the top choice for many visitors.