Chester Vacation Packages 2026 from $981

Chester flight + hotel vacation packages

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

Chateau Bedford, Trademark Collection by Wyndham

Birch Cove

$981

per person

Nov 4 - Nov 10

found 4 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Halifax (YHZ)

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-in and free internet in public areas. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Save 100% on your flight

$2,040

per person

Nov 4 - Nov 10

found 4 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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.

Residence Inn by Marriott Halifax Downtown

Downtown Halifax

$1,740

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Albany (ALB) 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.

Homewood Suites by Hilton Halifax-Downtown

Downtown Halifax

$1,590

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Albany (ALB) to Halifax (YHZ)

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

Hampton Inn by Hilton Halifax Downtown

Downtown Halifax

$1,512

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Albany (ALB) to Halifax (YHZ)

This hotel features an indoor pool and a 24-hour gym. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a terrace are also offered.

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

Sep 9 - Sep 10

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

$100 nightly

$117 total

Sep 16 - Sep 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

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12 Cookville NS

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$204 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Atlantic View Motel and Cottages

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

$178 nightly

$203 total

Aug 29 - Aug 30

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

Days Inn & Conference Center by Wyndham Bridgewater

50 North Street Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$168 total

Sep 6 - Sep 7

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

Oak Island Resort & Conference Centre

36 Treasure Drive Western Shore NS

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$175 total

Sep 1 - Sep 2

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

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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

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.

See properties

Frequently asked questions

How much are vacation packages to Chester?

With deals starting at just $981, 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.