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A large, two-story house with a steeply pitched roof and a chimney.

Chester

Vacations
Chester

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 $975, price is now CA $809 per person
CA $809
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Ottawa (YOW) 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 Dartmouth Crossing and Halifax Waterfront Boardwalk are located nearby.
Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

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

4.5 out of 5
Price was CA $8,179, price is now CA $6,046 per person
CA $6,046
per person
Aug 9 - Aug 14
found 12 hours ago
Roundtrip flight included
Ottawa (YOW) 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.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
Price was CA $1,004, price is now CA $813 per person
CA $813
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
Book a stay at this golf hotel in Yarmouth. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yarmouth Ferry Terminal and Firefighters' Museum are located nearby.
Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

2 out of 5
Price was CA $1,219, price is now CA $999 per person
CA $999
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
Book a stay at this golf motel in Garlands Crossing. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Trecothic Creek and Windsor Railway and West Hants Historical Society are located nearby.
Brier Island Lodge

Brier Island Lodge

3 out of 5
Price was CA $1,358, price is now CA $1,125 per person
CA $1,125
per person
Aug 20 - Aug 25
found 5 hours ago
Roundtrip flight included
Ottawa (YOW) to Halifax (YHZ)
Stay at this lodge in Westport. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Peter Island Lighthouse and Central Grove Picnic Park are located nearby.

Top Chester hotels deals

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is CA $236 per night
CA $236
CA $269 total
Aug 4 - Aug 5
includes taxes & fees
Book a stay at this business-friendly hotel in Western Shore. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Oak Island and Tancook Island are located nearby.
Pool
Pet-friendly
Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
Free cancellation
Reserve now, pay when you stay
The price is CA $243 per night
CA $243
CA $285 total
Jul 27 - Jul 28
includes taxes & fees
Book a stay at this business-friendly hotel in Halifax. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Dartmouth Crossing are located nearby.
Pet-friendly
Parking included
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
133 Kearney Lake Rd Halifax NS
Free cancellation
Reserve now, pay when you stay
The price is CA $224 per night
CA $224
CA $263 total
Jul 12 - Jul 13
includes taxes & fees
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 Dartmouth Crossing and Halifax Waterfront Boardwalk are located nearby.
Pool
Breakfast included
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
98 Chain Lake Dr Halifax NS
Free cancellation
Reserve now, pay when you stay
The price is CA $188 per night
CA $188
CA $221 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this family-friendly hotel in Beechville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Chocolate Lake Beach are located nearby.
Pool
Parking included
Old Orchard Inn

Old Orchard Inn

4 out of 5
153 Greenwich Rd. South Wolfville Ridge NS
Free cancellation
Reserve now, pay when you stay
The price is CA $212 per night
CA $212
CA $253 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this spa hotel in Wolfville Ridge. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Hennigar's Farm Market and Ken-Wo Golf Club are located nearby.
Pool
Spa
Stardust Motel Bedford

Stardust Motel Bedford

2.5 out of 5
1067 Bedford Highway Bedford NS
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $194 total
Jul 16 - Jul 17
includes taxes & fees
Stay at this motel in Bedford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dartmouth Crossing and Chocolate Lake Beach are located nearby.
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.

Stay near popular Chester attractions

Bayswater Beach Provincial Park

9.0/10 (26 reviews)
If a restful vacation is part of your travel plans, Bayswater Beach Provincial Park might be the perfect place to seek out during your trip to Bayswater. Make some time to visit the monuments while you're in the area.
See properties

Photos of local treasures

Browse Chester vacation photos for more inspiration

A calm lake with boats, a stone dock, and houses with a stone wall and trees in the background.
A greenhouse filled with various potted plants and flowers.
A storefront with a green sign reading "Kiwi Cafe" and a sign below stating "Reserved Kiwi Too".
A yellow building with a blue door and windows, a tree in front, and a silver car parked in front.
Sailboats on a calm lake with a forested shoreline.

Frequently asked questions

How much are vacation packages to Chester?
With vacation packages being sold from just CA $809, it's not necessary to blow out the credit card to visit Chester. Travelocity is here to help. Bundle flights, hotels and tours into a package and walk away with serious discounts. The more you book, the bigger the savings.
Where can I get the best vacation package deals for Chester?
It's difficult to beat Travelocity when it comes to piecing together your Chester package deal. There are as many as 400 airlines and 1,000,000 properties around the world to choose from. Plan your escape now and get ready to tick another destination off your must-see list.
Why should I book my Chester vacation package with Travelocity?
Because we believe in crafting unforgettable vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our customer support team is on hand 24/7 to ensure you're never alone. We also have a Price Match Guarantee, so you can book your getaway knowing you've scored the best deal possible. Find a lower price and we'll match it!
Can I save on my Chester car rental if I combine it with my hotel or flight?
You sure can. And our Chester vacation packages are the perfect way to do it. With only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Looking for things to do? Add some tours or experiences to your package and make savings on those too.
What is there to do in Chester?
You'll be happy to know Chester is brimming with amazing photo opportunities, however Oak Island and Saint Margarets Bay are among the best of them.