Chesley Vacation Rentals from ￥16,933: Search Short-Term Rentals

Q: What's the top vacation rental in Chesley?

GLOBALSTAY Brand New House in Port Elgin : This vacation home rental outside of Chesley is located near the beach and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

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Our top choices for Chesley vacation rentals

A cozy living room with a grey sofa, patterned cushions, and a wooden floor.

1. Williamsford Blacksmith Shop

Williamsford

David S.

￥19,636 total

includes taxes & fees

Oct 28 - Oct 29

A living room with a sofa, a TV, a small table, and a lamp.

2. Aspen Acres Cabin with BBQ and Private Deck

Chatsworth

Samantha T.

￥22,645 total

includes taxes & fees

Oct 21 - Oct 22

3. Historic 1873 Schoolhouse Retreat, West Grey

West Grey

Sandra

￥96,347 total

includes taxes & fees

Oct 26 - Oct 27

A rustic wooden barrel cabin with a chimney emitting smoke, surrounded by dense forest.

4. Tiny hill top home

Markdale

￥37,629 total

includes taxes & fees

Oct 26 - Oct 27

A kitchen with a dining area, a view of the outdoors, and a window.

5. Tiny House Rental in Markdale Perfect for a Couple's Retreat in Ontario

Markdale

￥38,797 total

includes taxes & fees

Oct 26 - Oct 27

A wooden hot tub with a metal frame, surrounded by rocks and trees.

6. Rural Cabin Surrounded by Beautiful Nature in Ontario

Markdale

￥37,104 total

includes taxes & fees

Nov 2 - Nov 3

A log cabin with a wooden door, a small porch, and a potted plant.

7. Rustic Cabin Incredible for Hiking and Outdoor Lovers in Ontario

Markdale

￥37,104 total

includes taxes & fees

Nov 2 - Nov 3

A rustic cabin interior with a wooden table, a window with curtains, a fireplace, and a bed.

8. Cute Wooden Cabin with Pond Views in Ontario

Markdale

￥38,797 total

includes taxes & fees

Oct 21 - Oct 22

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Top Chesley Hotel Reviews

Spark by Hilton Owen Sound

10/10 Excellent

"Good"

Staybridge Suites Port Elgin by IHG

10/10 Excellent

"I recently spent 3 nights at this hotel. Hotel has a good location with easy access to hwy 21. Can get down to Bayfield for an outing in a hour and 20 minutes. 8 km from Southampton. Beautiful quiet, large room with a full kitchen. Very clean with a comfortable bed and pillows. TV was a bit sketchy but wasn’t there to watch TV. Happy hour at the bar was friendly. I would definitely stay there again. Would like to try it in the summer. Hopefully all Staybridge Hotels are the same👍"

Travellers Motel - New Wing

8/10 Good

"The bed was firm. Room was nicely decorated and very clean. Towels are way too thin. We were in the room next to the door to the stairwell and it has a very loud closure, as well as hearing everyone talking going in and out. The TV was tricky to figure out. Overall, great value for the room!"

Travelodge by Wyndham Owen Sound

8/10 Good

"First of all we were not impressed by the fact that the motel permitted, even facilitates guests to smoke within 9 metres of the main entrance as well as on the patio areas outside of the rooms. According to the Ontario government's website there us to be no smoking within 9 metres of an entrance or windows. Several times we had to walk by people smoking and often they were blocking passage from the parking lot to the from door. Appreciate the mobility accessibility of the room yet challenges at all doors as they are manually operated. Given that it's 2026 having automatic doors, even ones operating by button would be expected. The room was clean, spacious and appears to be recently renovated /decorated. Bathroom is spacious though the tub not accessible for a person un a wheelchair. Overall a good place to stay and reasonably priced."

Find out more about Chesley

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Frequently asked questions

Can I find vacation rentals in Chesley?

Yes, we offer vacation rentals near the most popular sights in Chesley, or you can select a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Chesley?

GLOBALSTAY Brand New House in Port Elgin: This vacation home rental outside of Chesley is located near the beach and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

What can I see and do in Chesley?

While exploring the area, visit family-friendly sights like Story Book Park, or get outside and enjoy nature at Inglis Falls. In the larger area, you’ll find Playtime Casino Hanover and Saugeen Golf Club.

What are vacation rentals like in Chesley?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Chesley. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Chesley vacation rentals

1. Williamsford Blacksmith Shop

2. Aspen Acres Cabin with BBQ and Private Deck

3. Historic 1873 Schoolhouse Retreat, West Grey

4. Tiny hill top home

5. Tiny House Rental in Markdale Perfect for a Couple's Retreat in Ontario

6. Rural Cabin Surrounded by Beautiful Nature in Ontario

7. Rustic Cabin Incredible for Hiking and Outdoor Lovers in Ontario

8. Cute Wooden Cabin with Pond Views in Ontario

9. Quaint Off-Grid Cabin with Fire Pit Space in Ontario

10. Spruce, the tiny cabin in the woods

11. Jeronimo, Tipi for a group of 5

12. Oak, the tiny cabin in the woods

13. Maple, the tiny cabin in the woods

14. Forest View Chalet Unit with Hot Tub and Seasonal Salt Water Pool

15. Cochise, tipi for group of 5

16. Sitting Bull, Tipi for group of 6

17. Standing Bear, Tipi for group of 6

18. Chief Joseph, Large Tipi with central firepit

19. The Shores

20. Driftwood Haus

Find vacation rentals that suit your style

Top Chesley Hotel Reviews

Spark by Hilton Owen Sound

Nights Inn Owen Sound

Staybridge Suites Port Elgin by IHG

Comfort Inn Owen Sound

Travellers Motel - New Wing

Travelodge by Wyndham Owen Sound

Travellers Inn Hanover

Holiday Inn Express & Suites Port Elgin by IHG

Quality Inn

Find out more about Chesley

Frequently asked questions

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