Chester Vacation Packages 2025/2026 from $660

Chester flight + hotel vacation packages

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

Inn on the Lake

$660

per person

Nov 6 - Nov 9

found 11 hours ago

Roundtrip non-stop flight included

New York (JFK) to Halifax (YHZ)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Free self parking, a computer station, and luggage storage are also offered.

Lux Exec Home HFX Waterfront Pool Hot Tub

Save 100% on your flight

$1,072

per person

Nov 6 - Nov 9

found 11 hours ago

Roundtrip non-stop flight included

New York (JFK) 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.

Chateau Bedford, Trademark Collection by Wyndham

Birch Cove

$729

per person

Nov 6 - Nov 9

found 11 hours ago

Roundtrip non-stop flight included

New York (JFK) to Halifax (YHZ)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.

Residence Inn by Marriott Halifax Downtown

Downtown Halifax

$1,075

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Halifax (YHZ)

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

Cambridge Suites Hotel

Downtown Halifax

$861

per person

Dec 26 - Dec 30

found 15 hours ago

Roundtrip non-stop flight included

Phoenix (PHX) 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.

Top Chester hotels deals

Family Home In the Heart of the Village of Chester

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This vacation home features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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

$124 total

per night

Nov 1 - Nov 2

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

$92 total

per night

Oct 6 - Oct 7

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

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12, Cookville, NS

Free Cancellation

Reserve now, pay when you stay

$122 total

per night

Nov 1 - Nov 2

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

Surfside Inn

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

$199 total

per night

Oct 7 - Oct 8

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

Travelodge by Wyndham Bridgewater

49 North St, Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$133 total

per night

Nov 1 - Nov 2

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

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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 $660, 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.