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Chesley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesley vacation rentals

A room with a bed, a window, and a view of trees.

1. Aspen Acres Cabin with BBQ and Private Deck

Aspen Acres Cabin with BBQ and Private Deck
Chatsworth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay for 1 night in July. The apartment was super cute and very clean. It seemed to be recently built (or renovated). Check in was easy and the property was beautiful. Would happily stay here again!"
United States
Samantha T.
The price is CA $171
CA $203 total
includes taxes & fees
Sep 28 - Sep 29
Aspen Acres Cabin with BBQ and Private Deck
A cozy living room with a grey sofa, patterned cushions, and a wooden floor.

2. Williamsford Blacksmith Shop

Williamsford Blacksmith Shop
Williamsford
The price is CA $128
CA $176 total
includes taxes & fees
Sep 27 - Sep 28
Williamsford Blacksmith Shop
An aerial view of a coastal town with a marina, residential areas, and a beach.

3. GLOBALSTAY Brand New House in Port Elgin

GLOBALSTAY Brand New House in Port Elgin
4.0 star property
Saugeen Shores
8.6 out of 10, Excellent, (64 reviews)
"Close to everything , very clean spacious and quiet , We manged but the sofa bed didn't have blanket and pillows and bed sheet,"
Canada
Faramarz
The price is CA $153
CA $410 total
includes taxes & fees
Sep 27 - Sep 28
GLOBALSTAY Brand New House in Port Elgin
A sandy pathway leading to a beach with a clear view of the ocean and trees in the background.

4. Driftwood Haus

Driftwood Haus
3.0 star property
Saugeen Shores
9.2 out of 10, Wonderful, (109 reviews)
"Great location and all that we needed for our stay."
Canada
Saty
The price is CA $130
CA $237 total
includes taxes & fees
Sep 30 - Oct 1
Driftwood Haus
A rustic wooden barrel cabin with a chimney emitting smoke, surrounded by dense forest.

5. Tiny hill top home

Tiny hill top home
Markdale
The price is CA $189
CA $347 total
includes taxes & fees
Sep 27 - Sep 28
Tiny hill top home
A beach scene with people relaxing on chairs and towels, a clear sky, and a calm sea.

6. The Shores

The Shores
3.0 star property
Saugeen Shores
7.8 out of 10, Good, (49 reviews)
"Great size place, great location - easy to walk to everything on the main strip!"
Canada
Sydney
The price is CA $149
CA $168 total
includes taxes & fees
Oct 1 - Oct 2
The Shores

7. Historic 1873 Schoolhouse Retreat, West Grey

Historic 1873 Schoolhouse Retreat, West Grey
West Grey
The price is CA $295
CA $735 total
includes taxes & fees
Sep 27 - Sep 28
Historic 1873 Schoolhouse Retreat, West Grey
A hallway with a checkered rug leading to a bathroom.

8. 1 Bedroom Basement Apartment.

1 Bedroom Basement Apartment.
Owen Sound
9.0 out of 10, Wonderful, (2 reviews)
"As someone who travels annually to Owen Sound to spend time with friends I'm consistently looking for a place that's close to them and to fun places to meet, a place that's clean, and a place that's reasonably priced. This property checked all the boxes!! In fact, I'd like to keep it a secret to minimize the competition for next year's trip. The apartment is spacious and impeccably clean. It's cozy and comfortable, with all of the amenities to support a great stay - read great kitchen,...
United States
Jim F.
The price is CA $131
CA $207 total
includes taxes & fees
Sep 27 - Sep 28
1 Bedroom Basement Apartment.
A forest setting with three Adirondack chairs arranged around a campfire.

9. Rural Cabin Surrounded by Beautiful Nature in Ontario

Rural Cabin Surrounded by Beautiful Nature in Ontario
Markdale
The price is CA $264
CA $336 total
includes taxes & fees
Oct 20 - Oct 21
Rural Cabin Surrounded by Beautiful Nature in Ontario
A room with a sofa, a lamp, a window with a curtain, and a view of a forest.

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

Tiny House Rental in Markdale Perfect for a Couple's Retreat in Ontario
Markdale
The price is CA $275
CA $350 total
includes taxes & fees
Oct 19 - Oct 20
Tiny House Rental in Markdale Perfect for a Couple's Retreat in Ontario
A bedroom with a bed, a window, and a wall-mounted light fixture.

11. Cozy Home Away from Home

Cozy Home Away from Home
Markdale
4.0 out of 10, (1 review)
"The add did not represent the reality of the house. There was no furniture. We were not allowed to use master bedroom with ensuite, the bedrooms had mattress cover and pillows with cases. A duvet with no covering. Nothing in kitchen to prepare a meal or eat off of. We had a kitchen table and 4 chairs, a single bed in the living room only. We drove 7 hrs to spend time with family over Christmas holiday. When I called the owner he said lack of furniture and amenities were reflected in price. We...
Canada
Bryan Kathy S.
The price is CA $144
CA $223 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Home Away from Home
A forest with three white tents and a wooden hot tub.

12. Jeronimo, Tipi for a group of 5

Jeronimo, Tipi for a group of 5
Markdale
The price is CA $480
CA $695 total
includes taxes & fees
Sep 27 - Sep 28
Jeronimo, Tipi for a group of 5
A corner of a room with wooden walls, a metal ladder, and a metal shelf unit.

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

Rustic Cabin Incredible for Hiking and Outdoor Lovers in Ontario
Markdale
The price is CA $264
CA $336 total
includes taxes & fees
Oct 20 - Oct 21
Rustic Cabin Incredible for Hiking and Outdoor Lovers in Ontario
A metal-walled room with a wooden floor, a metal door, and a vertical pipe.

14. Cute Wooden Cabin with Pond Views in Ontario

Cute Wooden Cabin with Pond Views in Ontario
Markdale
The price is CA $275
CA $350 total
includes taxes & fees
Oct 19 - Oct 20
Cute Wooden Cabin with Pond Views in Ontario
A rustic log cabin with a porch, a fire pit, and a chair.

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

Quaint Off-Grid Cabin with Fire Pit Space in Ontario
Markdale
The price is CA $275
CA $350 total
includes taxes & fees
Oct 19 - Oct 20
Quaint Off-Grid Cabin with Fire Pit Space in Ontario
A rustic wooden barrel cabin with a chimney emitting smoke, surrounded by dense forest.

16. Ash, the tiny cabin in the woods

Ash, the tiny cabin in the woods
Markdale
The price is CA $400
CA $615 total
includes taxes & fees
Oct 1 - Oct 2
Ash, the tiny cabin in the woods
A rustic wooden barrel cabin with a chimney emitting smoke, surrounded by dense forest.

17. Spruce, the tiny cabin in the woods

Spruce, the tiny cabin in the woods
Markdale
The price is CA $400
CA $600 total
includes taxes & fees
Oct 1 - Oct 2
Spruce, the tiny cabin in the woods
A bunk bed with a checkered blanket, a wooden ladder, and a small enclosed space below the bed.

18. Lovely Cabin Rental with Outdoor Pool and Hot Tub near Markdale, Ontario

Lovely Cabin Rental with Outdoor Pool and Hot Tub near Markdale, Ontario
Markdale
The price is CA $749
CA $967 total
includes taxes & fees
Oct 20 - Oct 21
Lovely Cabin Rental with Outdoor Pool and Hot Tub near Markdale, Ontario
A cozy outdoor seating area with Adirondack chairs and a fire pit, surrounded by a wooden deck and a house with a 'TO THE BEACH' sign.

19. TOTAL RENOVATED Sauble Beach Cottage

TOTAL RENOVATED Sauble Beach Cottage
South Bruce Peninsula
9.6 out of 10, Exceptional, (32 reviews)
"Cute cottage, very well equipped and comfortable. Enjoyed our stay!"
United States
Diane W.
The price is CA $315
CA $592 total
includes taxes & fees
Sep 27 - Sep 28
TOTAL RENOVATED Sauble Beach Cottage
A rustic wooden barrel cabin with a chimney emitting smoke, surrounded by dense forest.

20. Maple, the tiny cabin in the woods

Maple, the tiny cabin in the woods
Markdale
The price is CA $480
CA $712 total
includes taxes & fees
Sep 27 - Sep 28
Maple, the tiny cabin in the woods
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.
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Top Chesley Hotel Reviews

Travelodge by Wyndham Owen Sound

Travelodge by Wyndham Owen Sound

10/10 Excellent
"Usual and favourite stay in Owen Soynd"
Theo 1-night trip
Posted 8 hours ago
Travelodge by Wyndham Owen Sound

Find out more about Chesley

Everything you need to know about Chesley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesley vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesley vacation rentals we have selected for you start as low as CA $168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesley rentals

At Expedia, we put the best Chesley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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.