Vacation rentals in Hockley

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Top-rated vacation rentals in Hockley

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Top guest favorite

A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.

Cabin in Arthur

4.99 out of 5 average rating, 408 reviews

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side! An hour from Toronto.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom 2nd BR bunk beds w/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly

Top guest favorite

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

Guest suite in Orangeville

4.92 out of 5 average rating, 847 reviews

Cozy HotTub & Fireplace-Headwaters Spring Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Top guest favorite

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

4.95 out of 5 average rating, 339 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Top guest favorite

The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.

Guesthouse in Barrie

5 out of 5 average rating, 250 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Top guest favorite

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

4.95 out of 5 average rating, 147 reviews

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

Top guest favorite

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

Guesthouse in Halton Hills

4.92 out of 5 average rating, 172 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. Firewood is included, adding great value. You WILL hear wildlife and farm animals here. A pet is welcome, please include them under “guests.”

Guest favorite

A charming A-frame cabin is surrounded by tall trees, featuring a triangular roof and wooden siding. The entrance includes a white door with a window above, complemented by a small wooden deck with stone accents.

Cabin in Clarksburg

4.96 out of 5 average rating, 123 reviews

Tiny A-Frame near the Bruce Trail

Find yourself nestled among pines trees just steps from the Bruce Trail! This 100 sq. ft. tiny A-Frame offers cozy comfort with two stackable twin beds that convert into a queen (side-by-side) when desired. Amenities include the essentials: BBQ, drinking and dish water, power box to charge devices and a small light, plus an outhouse with a composting toilet. Centrally located near Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

Superhost

An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.

Tiny home in Acton

4.84 out of 5 average rating, 122 reviews

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private and quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. This trailer is perfect for 2 to 4 adults looking to relax and enjoy the scenery or explore the lake on kayak or fishing in the lake or enjoy some outdoor movies or campfire or under the stars.

Top guest favorite

The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.

Tiny home in Arthur

4.97 out of 5 average rating, 367 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top guest favorite

A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.

Loft in Mono

4.98 out of 5 average rating, 159 reviews

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

Top guest favorite

A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.

Place to stay in Wasaga Beach

4.99 out of 5 average rating, 376 reviews

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Top guest favorite

The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.

Cabin in Flesherton

4.96 out of 5 average rating, 112 reviews

MapleHaven Cabin @ Lake Eugenia

A rustically elegant log cabin sitting on an acre of beautiful mature maple trees on a quiet dead-end street. Find peace and tranquility in the rustic atmosphere the log cabin setting provides, but enjoy all of the comforts of home. Enjoy 3 bedrooms ,2 baths with a master bedroom that features a coffee bar and covered balcony . Located at Lake Eugenia, in the heart of the scenic Beaver Valley, a 4 seasons playground. Walking distance to public beach/boat launch.