Book Exclusive Chester Vacation Packages

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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.
Burgundy Dream Bed and Breakfast

Burgundy Dream Bed and Breakfast

2 out of 5
Price was CA $481, price is now CA $429 per person
CA $429
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
Stay at this B&B in Waverley. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dartmouth Crossing and Shubie Park are located nearby.
The Lord Nelson Hotel & Suites

The Lord Nelson Hotel & Suites

4.5 out of 5
Downtown Halifax
Price was CA $573, price is now CA $502 per person
CA $502
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
Book a stay at this luxury hotel in Halifax. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was CA $599, price is now CA $530 per person
CA $530
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.
Seasons Inn Halifax

Seasons Inn Halifax

2.5 out of 5
Fairview
Price was CA $545, price is now CA $487 per person
CA $487
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
Book a stay at this golf hotel in Halifax. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was CA $534, price is now CA $478 per person
CA $478
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop 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.

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
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $175 total
Nov 8 - Nov 9
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 Valverde Studio Gallery are located nearby.
Pool
Pet-friendly
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Chester NS
Get rates
Book a stay at this beach cottage in East Chester. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Goat Lake and Graves Island Provincial Park are located nearby.
Kitchen
Washer
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Western Shore NS
The price is CA $340 per night
CA $340
CA $573 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this vacation home in Western Shore. Enjoy laundry facilities, an in-room coffeemaker, and a hot tub. Popular attractions Oak Island and Valverde Studio Gallery are located nearby.
Pool
Hot tub
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 $174 per night
CA $174
CA $204 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this business-friendly hotel in Halifax. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
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 $170 per night
CA $170
CA $200 total
Nov 1 - Nov 2
includes taxes & fees
Stay at this 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 Halifax Citadel are located nearby.
Pool
Pet-friendly
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 $149 per night
CA $149
CA $175 total
Nov 1 - Nov 2
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 Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
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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 $429, 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.