Vacation rentals in Chesley Lake

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Top-rated vacation rentals in Chesley Lake

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Guest favorite

Home in Shallow Lake

4.97 out of 5 average rating, 64 reviews

Hindman House: Historic, restful, fully-equipped

Set back on a quiet road on over half an acre, Hindman House, just 20 minutes north of Owen Sound, invites you to relax and recharge in any season. The house is a cherished historic gem fully-equipped with all the amenities for 21st century comfort and function. A chef-approved kitchen, comfortable seating areas for relaxing with a book or Netflix, beautiful rural surroundings inviting you out on the porch or for a walk. Close to the Bruce Trail & Sauble Beach and an hour's drive to Tobermory.

Nov 25 – Dec 2

ﺩ.ﺇ536 per night

Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 191 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Oct 11 – 18

ﺩ.ﺇ517 per night

Guest favorite

Guest suite in Southampton

4.92 out of 5 average rating, 64 reviews

Fresh and Clean Suite #4 at Rankin Rentals

Located on the North End of Southampton a quick drive, a 20 min cycle, 30 min walk to Southampton’s picturesque downtown & beaches. Shops, restaurants; walking, jogging, cycling, golfing, fishing, kayaking, boating, Art Gallery, Museum, beaches & Lake Huron sunsets all in close vicinity Whether visiting Southampton area for work or play our newly renovated & appointed private efficiency suites are fresh and comfortable. Queen-size bed. Max 2 occupants. No Pets. No bicycle storage in the suites.

Jul 14 – 21

ﺩ.ﺇ472 per night

Guest favorite

Guesthouse in Kemble

5.0 out of 5 average rating, 49 reviews

Cozy Bunkie on a Scenic Hilltop with Goats

Welcome to our charming bunkie nestled on a hilltop with breathtaking views of the Niagra Escarpment! Enjoy a premium glamping experience. This quiet escape comes with all the creature comforts like a hot shower, wifi, and plugs to charge your devices. Nature enthusiasts will love the trails that wind through the property. We have baby goats, fruit trees, and flowers depending on the season. We would be delighted to introduce you to our goats in their pasture. Please ask us for a tour.

Oct 4 – 11

ﺩ.ﺇ355 per night

Guest favorite

Cottage in South Bruce Peninsula

4.94 out of 5 average rating, 31 reviews

Lakeview Luxury: Modern Bruce County Cottage Oasis

Welcome to Shorehill Lodge, your serene retreat in the heart of South Bruce Peninsula, boasting stunning Chesley Lake vistas and serene forest surroundings. Experience the essence of every season, from the vibrant blooms of spring to the sun-drenched days of summer. Indulge in the comfort of our traditional yet modern lodge, where cozy interiors beckon with a curated collection of books and games. Our well-appointed kitchen invites culinary adventures, ensuring every meal feels like a feast.

Sep 12 – 19

ﺩ.ﺇ621 per night

Guest favorite

Guesthouse in Kemble

4.82 out of 5 average rating, 133 reviews

Waterfront Sunrise Cottage

Private waterfront cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. With a 150 feet of shoreline shared only with a neighbouring cottage, enjoy the stunning sunrises, relax on a lounger, go for a swim, kayak, paddle board, go fishing or have a camp fire and stargaze. Use our cottage as a jumping off point for many hikes along the Bruce Trail, Sauble Beach (35min), Tobermory (70min) and many more. Or just work from here while enjoying the great view and wifi.

May 7 – 14

ﺩ.ﺇ353 per night

Guest favorite

Bungalow in Georgian Bluffs

4.98 out of 5 average rating, 97 reviews

A Naturalist's Paradise - Shepard Lake waterfront

Located on a tranquil, private, inland lake on the base of the Bruce Peninsula. Spacious apartment (lower level of bungalow-one unit, no shared spaces), perfect getaway for outdoor enthusiasts. Very private location with secluded sitting area, yard & dock. Boats are exclusive for your use. Enjoy fishing/bird watching. Close to hiking trails, golf courses & beautiful beaches for swimming just minutes away. Relax on the dock, read, BBQ & enjoy campfires. See our "host guidebook" in the ad.

Nov 22 – 29

ﺩ.ﺇ371 per night

Guest favorite

Guesthouse in Neustadt

4.92 out of 5 average rating, 303 reviews

Bunkie in the Country

Now Open! The bunkie has a great view of the sunrise. It's a quiet rural area (please note it is a GRAVEL road). Good for couples, solo adventurers, hunters, someone looking to be outside of town. The bunkie is located approx. 30 feet behind our home. We have 2 large dogs on site (live in the house). For allergenic reasons and safety of other animals, we do not allow pets. May not be suitable for those with mobility issues (small hill & stairs). The bunkie has heat and A/C!

Apr 11 – 18

ﺩ.ﺇ204 per night

Guest favorite

Cottage in Allenford

4.94 out of 5 average rating, 16 reviews

Barefoot Bay - 5 bedroom Waterfront Cottage

Welcome to Barefoot Bay Cottage, your private waterfront paradise. Year round cottage located in the beautiful South Bruce Peninsula on Chesley Lake. Drive your snowmobile right to the OFSC snowmobile trail system. Lake freezes and very popular for ice fishing! Close to ATV trails. 15 minutes to SawMill cross country ski trail. Located minutes from Sauble Beach with its 11km sandy beach. Just a short drive away are the towns of Southampton, Port Elgin and Owen Sound.

Jan 28 – Feb 4

ﺩ.ﺇ1,225 per night

Guest favorite

Cabin in Tara

4.95 out of 5 average rating, 77 reviews

Rustic Pines Cabin Offgrid

Located just outside of the little town of Tara. And 20 min from Sauble beach, Port Elgin and Southampton.Come relax and unwind in this little cabin tucked away in 5 acres of bush on an ongoing crop farm. It is OFF GRID but has a propane refrigerator, propane heater for those cool spring and fall mornings and cooktop as well as a grill for over the fire. And water from a spring fed well to wash dishes, cook or even try out the outdoor heated camping shower.

Aug 17 – 24

ﺩ.ﺇ425 per night

Guest favorite

Guest suite in Meaford

4.95 out of 5 average rating, 172 reviews

The Beach Button

Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!

Mar 27 – Apr 3

ﺩ.ﺇ468 per night

Guest favorite

Apartment in Owen Sound

4.98 out of 5 average rating, 153 reviews

Victorian on Main Street

Beautiful two bedroom duplex centrally located in Owen Sound. Our century home has been fully updated to provide a comfortable stay, while holding on to yesterdays charm. A short walk to downtown, restaurants, and Harrison Park. Discounted rates are available for weekly and monthly (or longer) stays, just enter your dates to see the lower price.

Dec 2 – 9

ﺩ.ﺇ439 per night