Chester Vacation Packages 2026 from $423

Chester flight + hotel vacation packages

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

Inn on the Lake

$423

per person

Apr 7 - Apr 9

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

HFX Airport Hotel

$881

per person

Apr 3 - Apr 10

found 9 hours ago

Roundtrip flight included

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

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

$483

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Nalu Retreat & Nordic Spa

$844

per person

Feb 20 - Feb 23

found 24 hours ago

Roundtrip non-stop flight included

New York (NYC) to Halifax (YHZ)

This holiday park doesn't skimp on freebies - guests receive free WiFi and free self parking. A hot tub is also provided.

Sandman Signature Dartmouth Hotel & Suites

$630

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Halifax (YHZ)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and luggage storage are also offered on site.

Top Chester hotels deals

Travelodge by Wyndham Bridgewater

49 North St Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Jan 15 - Jan 16

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

$114 nightly

$130 total

Jan 18 - Jan 19

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

Brigantine Inn & Suites

82 Montague Street Lunenburg NS

Get rates

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free.

Free WiFi

Restaurant

Bridgewater Hotel

35 High St. Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$84 total

Jan 13 - Jan 14

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

Days Inn & Conference Center by Wyndham Bridgewater

50 North Street Bridgewater NS

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Jan 18 - Jan 19

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

Black Forest Cabins

15 Longhill Rd Mahone Bay NS

$168 nightly

$192 total

Feb 1 - Feb 2

Total with taxes and fees

A full-service spa is available at this cabin. Take advantage of the free self parking.

Parking included

Free WiFi

Don't see what you're looking for?

See all available properties in Chester

View all properties

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.

Chester Art Center

You can spend an afternoon browsing the exhibits at Chester Art Center during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.

Amicus Gallery

You can spend time studying the exhibits at Amicus Gallery in 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 $423, 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.