Book Exclusive Chester Vacation Packages

Choose one or more items to build your trip:

Chester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was CA $1,000, price is now CA $886 per person
CA $886
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Dartmouth. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Dartmouth Crossing are located nearby.
Brewery Park Hotel

Brewery Park Hotel

3.5 out of 5
North End
Save 100% on your flight
Price was CA $1,371, price is now CA $941 per person
CA $941
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Halifax (YHZ)
Stay at this hotel in Halifax. Enjoy free WiFi, Netflix, and premium bedding. Popular attractions Halifax Waterfront Boardwalk and Casino Nova Scotia are located nearby.
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

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

4.5 out of 5
Save 100% on your flight
Price was CA $2,754, price is now CA $2,099 per person
CA $2,099
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Halifax (YHZ)
Book a stay at this luxury vacation home in Halifax. Enjoy free WiFi, free parking, and private pools. Popular attractions Halifax Waterfront Boardwalk and Scotiabank Centre are located nearby.
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was CA $1,392, price is now CA $1,081 per person
CA $1,081
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Halifax. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
Red George Inn and Suites

Red George Inn and Suites

2 out of 5
Downtown Halifax
Price was CA $1,050, price is now CA $927 per person
CA $927
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
Book a stay at this family-friendly hotel in Halifax. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Halifax Waterfront Boardwalk and Scotiabank Centre are located nearby.

Top Chester hotels deals

Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St. Bridgewater NS
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
CA $128 total
Nov 1 - Nov 2
includes taxes & fees
Stay at this hotel in Bridgewater. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kinsmen Field and Wile Carding Mill Museum are located nearby.
Pet-friendly
Parking included
Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

2.5 out of 5
50 North Street Bridgewater NS
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $157 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Bridgewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bridgewater Mall and Lunenburg County Lifestyle Centre are located nearby.
Breakfast included
Parking included
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
Get rates
Book a stay at this beach motel in Lunenburg. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Bluenose Golf Club and Lightship Brewery are located nearby.
On private beach
Parking included
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12 Cookville NS
Free cancellation
Reserve now, pay when you stay
The price is CA $167 per night
CA $167
CA $191 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this business-friendly hotel in Cookville. Enjoy free breakfast, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lunenburg County Lifestyle Centre and Cookville Provincial Park are located nearby.
Pool
Breakfast included
Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $143 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this hotel in Bridgewater. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bridgewater Mall and Lunenburg County Lifestyle Centre are located nearby.
Breakfast included
Pet-friendly
The Homeport Motel

The Homeport Motel

2 out of 5
167 Victoria Road Lunenburg NS
Free cancellation
Reserve now, pay when you stay
The price is CA $105 per night
CA $105
CA $120 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this motel in Lunenburg. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pajo's Bowling Alley and Lunenburg Farmers' Market are located nearby.
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.

Stay near popular Chester attractions

Chester Golf Club

8.4/10 (28 reviews)
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.
See properties

Chester Vacations

If you can't remember the day your geography teacher told your class where Chester is, you don't have to stress. With a bit of help from us, you'll be able to find it on your map in no time!

Chester sits in Nova Scotia. Also, Halifax, a noteworthy location, is 35 miles (56 kilometers) away.

This area of Nova Scotia has a population of about 2,000 people.

Places to visit in Chester

History is full of lessons. Drink in the knowledge and become more familiar with the past at Lordly House Museum. Need some more ideas? Get into your khakis and reach for your luckiest clubs. If you're desperate to indulge in a day on the fairways, lock in a tee time at Chester Golf Club. But that's not all there is. Find stimulating ideas and magnificent artwork at Amicus Gallery. It maintains a rotating roster of collections that are sure to interest art fans.

Where do you fly into for Chester?

Get set for some unique adventures in Chester. Once you've wandered out of Stanfield International Airport (YHZ), the center of town will be 45 miles (72 kilometers) to the southwest.

Frequently asked questions

How much are vacation packages to Chester?
With deals starting at just CA $886, 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.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A large, two-story house with a steeply pitched roof and a chimney.
A calm lake with several sailboats and a few motorboats.
A coastal scene with multiple boats anchored in the water, a dock, and a building with a green roof.
A large, two-story house with a white porch and multiple windows.
A storefront with a green sign reading "Kiwi Cafe" and a sign below stating "Reserved Kiwi Too".

Explore More Ways to Travel with Travelocity