Chester Vacation Packages 2026 from $392

Chester flight + hotel vacation packages

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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Save 100% on your flight

$392

per person

Oct 6 - Oct 11

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. Self parking, a library, and dry cleaning are also offered.

Coastal Inn Halifax

$534

per person

Oct 6 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

An indoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and dry cleaning are also on offer.

The Lord Nelson Hotel & Suites

Downtown Halifax

$668

per person

Oct 9 - Oct 13

found 15 hours 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 business center and free WiFi in public areas. Self parking, a garden, and a hair salon are also offered.

Future Inns Halifax

Clayton Park West

$529

per person

Oct 6 - Oct 11

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. Free self parking, a coffee shop, and a lobby fireplace are also offered.

Cameo Hotel and Suites

Downtown Halifax

$663

per person

Oct 9 - Oct 13

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

Free WiFi in public areas, express check-in, and express check-out are available at this aparthotel. Luggage storage and laundry facilities are also provided.

Top Chester hotels deals

Travelodge by Wyndham Bridgewater

49 North St Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$161 total

Oct 4 - Oct 5

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

Bridgewater Hotel

35 High St. Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Sep 6 - Sep 7

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

Oak Island Resort & Conference Centre

36 Treasure Drive Western Shore NS

$196 nightly

$223 total

Sep 20 - Sep 21

Total with taxes and fees

A marina and an indoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 6 conference rooms, along with free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12 Cookville NS

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$202 total

Sep 14 - Sep 15

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 Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$164 total

Sep 27 - Sep 28

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

Atlantic View Motel and Cottages

230 Mason's Beach Road, RR#2 Lunenburg NS

$144 nightly

$164 total

Oct 1 - Oct 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

On private beach

Parking included

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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.

Stay near popular Chester attractions

Chester Playhouse

8.6/10 (12 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.

See properties

Frequently asked questions

How much are vacation packages to Chester?

With deals starting at just $392, 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.