Chester Vacation Packages 2025/2026 from $659

Chester flight + hotel vacation packages

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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

$659

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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 library, and dry cleaning are also offered.

Brewery Park Hotel

North End

$740

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Halifax (YHZ)

Free WiFi in public areas and luggage storage are available at this hotel.

Cambridge Suites Hotel

Downtown Halifax

$684

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Halifax (YHZ)

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

Lux Exec Home HFX Waterfront Pool Hot Tub

$1,360

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Prince George Hotel

Downtown Halifax

$707

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Halifax (YHZ)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and concierge services.

Top Chester hotels deals

Travelodge by Wyndham Bridgewater

49 North St, Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$131 total

Nov 24 - Nov 25

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

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12, Cookville, NS

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$122 total

Nov 27 - Nov 28

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

Smugglers Cove Inn

139 Montague Street, Lunenburg, NS

Free Cancellation

Reserve now, pay when you stay

Get rates

Free WiFi in public areas and luggage storage are available at this hotel.

Free WiFi

Air conditioning

The Homeport Motel

167 Victoria Road, Lunenburg, NS

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$87 total

Nov 14 - Nov 15

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 grocery/convenience store are also on offer.

Parking included

Free WiFi

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

$94 nightly

$111 total

Nov 27 - Nov 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

Bridgewater Hotel

35 High St., Bridgewater, NS

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$75 total

Nov 27 - Nov 28

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

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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

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.

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.

St. Stephen's Church

After visiting St. Stephen's Church, make a plan to see the other sights and activities in Chester. Amble around this family-friendly area's waterfront or experience its entertainment venues.

Frequently asked questions

How much are vacation packages to Chester?

With deals starting at just $659, 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.