Book Exclusive Chesley Vacation Packages

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Chesley flight + hotel packages

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

Dreamers Writing Farm

1.5 out of 5
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Guelph (XIA)
Book a stay at this golf holiday park in South Bruce Peninsula. Enjoy free parking, a garden, and a picnic area. Popular attractions memorial Park and Whispering Pines are located nearby.
Stop 21 Motel

Stop 21 Motel

2 out of 5
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Guelph (XIA)
Stay at this motel in Saugeen Shores. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Southampton Beach and Southampton Art School and Gallery are located nearby.
The Sands

The Sands

2 out of 5
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Guelph (XIA)
Book a stay at this beach hotel in Sauble Beach. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ascent Aerial Park and Sauble Speedway are located nearby.
The Shores

The Shores

3 out of 5
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Guelph (XIA)
Stay at this 3-star apartment in Saugeen Shores. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Southampton Art School and Gallery and Bruce County Museum & Cultural Centre are located nearby.
Leelas Villa Inn Flesherton

Leelas Villa Inn Flesherton

3 out of 5
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Guelph (XIA)
Stay at this 3-star hotel in Grey Highlands. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Artsonten and Hoggs Falls are located nearby.

Top Chesley hotels deals

Best Western Inn On The Bay

Best Western Inn On The Bay

2.5 out of 5
1800 2nd Avenue East, Owen Sound, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $190 per night
CA $190
CA $223 total
includes taxes & fees
Apr 24 - Apr 25
Book a stay at this eco-certified hotel in Owen Sound. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Harry Lumley Bayshore Community Centre and Tom Thomson Art Gallery are located nearby.
Hot tub
Pet-friendly
Travelodge by Wyndham Port Elgin

Travelodge by Wyndham Port Elgin

2 out of 5
235 Goderich St, Saugeen Shores, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $82 per night
CA $82
CA $92 total
includes taxes & fees
Apr 23 - Apr 24
Stay at this motel in Saugeen Shores. 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 Holiday Golf Club and Saugeen Rail Trail Trailhead are located nearby.
Super 8 by Wyndham Port Elgin

Super 8 by Wyndham Port Elgin

2 out of 5
5129 Highway 21 South, Saugeen Shores, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $128 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly motel in Saugeen Shores. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Holiday Golf Club and Port Elgin Beach are located nearby.
Pool
Hot tub
Travelodge by Wyndham Owen Sound

Travelodge by Wyndham Owen Sound

2 out of 5
880 10th St E, Owen Sound, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $81 per night
CA $81
CA $95 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Owen Sound. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Roxy Theatre and Gallery de Boer, Fine Art & Jazz are located nearby.
Comfort Inn Owen Sound

Comfort Inn Owen Sound

2.5 out of 5
955 9th Ave E, Owen Sound, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $125 per night
CA $125
CA $151 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Owen Sound. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Roxy Theatre and Gallery de Boer, Fine Art & Jazz are located nearby.
Breakfast included
Pet-friendly
Quality Inn

Quality Inn

2.5 out of 5
950 Sixth St East, 9th Ave and Sixth St East, Owen Sound, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $93 per night
CA $93
CA $112 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this eco-certified hotel in Owen Sound. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Roxy Theatre and Gallery de Boer, Fine Art & Jazz 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.

Chesley Vacations

Unintentionally stumbling upon somewhere new is precisely what traveling is all about, But of course, it certainly never hurts to find out a few things about the area before you go. We'll get you up to speed on the basics about Chesley.

You'll find this Owen Sound neighborhood 20 miles (32 kilometers) to the south of the downtown action.

Owen Sound is home to some 23,000 locals.

Places to visit in Chesley

The Owen Sound region offers lots of opportunities to have fun outdoors. Why not consider going mountain biking while you're in the area? After you've checked that off your list, create some more glorious memories by going mountain climbing.

Where do you fly into for Chesley?

Stow your tray table, switch off the in-flight entertainment, and get ready to hit the tarmac at Billy Bishop Regional Airport (YOS). Want some good news? You'll be only 25 miles (40 kilometers) to the northeast of Chesley.

Frequently asked questions

How much are vacation packages to Chesley?
Your vacation fantasies can become reality in Chesley for as little as CA $468. Our affordable package deals include flights and hotels, and they’ll make your booking a cinch. All you’ll have to concentrate on is having a good time.
Where can I get the best vacation package deals for Chesley?
Picking up an amazing package deal to Chesley is a cinch with Travelocity. With access to 400 air carriers and 665,000 properties around the world, you won’t be short of choice when selecting your hotels and flights.
Why should I purchase my Chesley vacation package with Travelocity?
Whether you’re in search of the ultimate unplugged getaway or after the fun and excitement of the big city, booking everything with Travelocity saves you time, hassle and money. No need to comb through countless websites to find the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need anything at all.
Will I save money on my Chesley car rental if I book it with a hotel or flight?
Absolutely — and booking one of our Chesley vacation packages is the easiest way to go about this. Bundle any combination of a car, flight, hotel and experience and get access to great discounts. The more you bundle, the more you save. There are loads of impressive sights in and around Chesley to put on your bucket list, including CN Tower (150 kilometersfrom Chesley). Nothing tops discovering places like this with the freedom of your own wheels.
What is the best time of year to go to Chesley?
If you’re watching your pennies, is an ideal month to explore here, while is the most expensive time of the year. is generally regarded as high season. If you’re hoping to dodge the crowds, tend to be quieter.
Where should I stay when visiting Chesley?
After a wonderful day of sightseeing around Chesley, rest your head at the Saugeenview Family Getaway. This top option has everything you need for a comfortable stay.
Can I go on vacation to Chesley at this time?
Don’t head to Chesley without up-to-date facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor can fill you in. Our local experts have pulled together all the info you need to make your vacation and flight as hassle-free as possible.

Photos of local treasures

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