Chester Vacation Packages 2026 from $763

Chester flight + hotel vacation packages

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

Inn on the Lake

$763

per person

Jun 12 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) 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.

Sandman Signature Dartmouth Hotel & Suites

$885

per person

Jun 12 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) 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. Enjoy the hot tub and perks like free self parking.

The Sutton Place Hotel Halifax

Downtown Halifax

$1,362

per person

Jun 12 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) 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.

Chateau Bedford, Trademark Collection by Wyndham

Birch Cove

$843

per person

Jun 12 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Halifax (YHZ)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Coastal Inn Halifax

$826

per person

Jun 12 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Halifax (YHZ)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the children's pool and onsite laundry facilities. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.

Top Chester hotels deals

Chester Back Harbour Exclusive providing direct access to water via private dock

Chester Basin NS

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This vacation home features laundry facilities.

Large, modern Cape Cod style cottage in oceanside charming town

Chester NS

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This cottage features laundry facilities.

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12 Cookville NS

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$131 total

Apr 25 - Apr 26

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

$123 nightly

$140 total

Apr 18 - Apr 19

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

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This houseboat includes a garden and barbecue grills.

The Homeport Motel

167 Victoria Road Lunenburg NS

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$107 total

Apr 25 - Apr 26

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

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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.

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.

Frequently asked questions

How much are vacation packages to Chester?

With deals starting at just $763, 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.