Chester Vacation Packages 2026 from $556

Chester flight + hotel vacation packages

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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

$556

per person

Jun 11 - Jun 15

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Sutton Place Hotel Halifax

Downtown Halifax

$894

per person

May 17 - May 21

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Halifax (YHZ)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a hot tub on site, and laundry facilities and concierge services are also offered.

Red George Inn and Suites

Downtown Halifax

$833

per person

Jun 11 - Jun 15

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Halifax (YHZ)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. A garden, luggage storage, and laundry facilities are also on offer.

Prince George Hotel

Downtown Halifax

$1,028

per person

Jun 11 - Jun 15

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Brewery Park Hotel

North End

$801

per person

Jun 11 - Jun 15

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Halifax (YHZ)

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

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

$114 nightly

$129 total

Apr 12 - Apr 13

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.

Smugglers Cove Inn

139 Montague Street Lunenburg NS

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$128 total

Apr 5 - Apr 6

Total with taxes and fees

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

Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route

Pleasantville NS

Get rates

This houseboat includes a garden and barbecue grills.

The Homeport Motel

167 Victoria Road Lunenburg NS

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$105 total

Apr 8 - Apr 9

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.

The Dockside Inn & Restaurant

84 Montague Street Lunenburg NS

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Apr 5 - Apr 6

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. WiFi in public areas is free. Luggage storage is also provided.

Travelodge by Wyndham Bridgewater

49 North St Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$112 total

Apr 5 - Apr 6

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.

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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 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.

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 $556, 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.