Vacation rentals in Annan

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Top-rated vacation rentals in Annan

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Top guest favorite

The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.

Tiny home in Kimberley

4.98 out of 5 average rating, 166 reviews

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

Top guest favorite

The entrance showcases intricate woodwork and architectural details, with a grand staircase leading to the upper level. A large door opens to the outside, and a vintage chandelier illuminates the inviting foyer, highlighting the craftsmanship of the historic home.

Home in Owen Sound

4.98 out of 5 average rating, 235 reviews

The Butchart Estate: your perfect family retreat!

Give them a holiday to remember. With fresh air & freshwater beaches. Escarpment views, grottos & waterfalls. It's a great time to get yourself a little more Canada in beautiful Grey-Bruce. Settle in to our beautiful and well-equipped heritage home. Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, play board games galore. Outdoors, we're famous for our hills, forests, lakes and rivers. But don't miss the music, museums, and amazing foodie scene.

Guest favorite

A cozy loft bedroom features a spacious bed dressed in soft white and blue linens. Light wood flooring complements the blue and dark walls, while bedside tables with lamps provide gentle illumination. A plush robe hangs nearby, and a small rack holds towels for convenience.

Guest suite in Chatsworth

4.86 out of 5 average rating, 389 reviews

Settler's Loft in Log Home

This charming original log home is set amongst rock fences and mature maples on 80 acres of reforested farmland. This two-storey suite sleeps up to 5 guests, has 2 bedrooms, 4-piece bathroom, kitchenette, living area, deck, & private balcony. Trails for exploring, campfire ring, and large grassy area for outdoor games. Brand new AC system. Very close to OFSC snowmobile trails. (Note - barn access is for weddings only) NO pets >> 40 minute drive to Blue Mountain; 30 minutes to Lake Huron beaches

Superhost

A charming modern cottage is set against a backdrop of lush greenery and clear blue skies. The exterior features large glass windows and a sloped roof. A patio area with natural stone and comfortable outdoor seating is highlighted, providing a welcoming space to enjoy the views.

Cottage in Meaford

4.91 out of 5 average rating, 189 reviews

Cosy and modern cottage on beautiful Georgian Bay

Enjoy panoramic views of Georgian Bay from this charming modern cottage on Paynter's Bay. Only eight minutes from Owen Sound, our cottage also borders on the quiet and beautiful Hibou Conservation Area where you can enjoy birding, hikes in forest and shoreline, and a great sandy beach and modern playground for the kids. Cuddle up next to the gorgeous modern Morso woodstove. Adventure awaits you with lots of skiing, biking, snowmobiling and the waterfall wonders of the Niagara Escarpment nearby.

Top guest favorite

A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.

Cottage in Southgate

4.98 out of 5 average rating, 128 reviews

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Top guest favorite

Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.

Place to stay in Chatsworth

5 out of 5 average rating, 119 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Top guest favorite

The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.

Yurt in Meaford

4.99 out of 5 average rating, 154 reviews

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Guest favorite

The image captures a serene sunset over the water, with vibrant colors reflecting off the lake surface. Two trees silhouette against the backdrop, and gentle waves can be seen lapping at the shore, creating a tranquil atmosphere.

Cottage in Kemble

4.84 out of 5 average rating, 164 reviews

Georgian Bay Waterfront Oasis

Waterfront Cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. We have 150 feet of private shoreline. Enjoy the east facing view and stunning sunrises, relax on a lounger, go for a swim, fish off the shore or in the small row boat, 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.

Superhost

The spacious upper deck features a hot tub, dining table with umbrella, and comfortable seating. A grill is positioned in the corner. Surrounding greenery and open fields create a peaceful setting, with a clear blue sky overhead enhancing the outdoor experience.

Loft in Owen Sound

4.88 out of 5 average rating, 109 reviews

Brand New Country View Loft with Hot Tub

Conveniently located between Owen Sound and Meaford on a beautiful 7 acre property surrounded by fields and trees, this brand new bright and open loft has endless attractions within a 50 km radius. Whether you are a skier going to Blue Mountain or want to enjoy the beach at Sauble, this place can be your home base while you explore our wonderful area. Coffin Ridge Winery:5 mins, Blue Moutains:30mins, Bruce Trail:5mins, Sauble:30mins, Bruce Penninsula:45mins.

Top guest favorite

A cozy living room features a teal sofa, a brown armchair, and a wooden television stand. A flat-screen TV is mounted on the wall. A patterned area rug covers the hardwood floor, while a coffee table with a geometric design sits in the center. Natural light enters through a window.

Apartment in Owen Sound

4.96 out of 5 average rating, 154 reviews

Suite on the Creek

Keep it simple at this peaceful and centrally located walkout apartment. The suite backs onto the Niagara escarpment and sections of the Bruce Trail. Though you’ll feel secluded in nature, head out front and you can walk downtown in less than 15 minutes. Rest well in the king-sized bed that looks out onto the walking bridge in the back yard. Enjoy cozy evenings in with a movie and a fire, or relax with a book in your private backyard sitting area.

Superhost

A scenic view of Georgian Bay is displayed with lush green landscapes extending towards the horizon. Rolling hills and cliffs are visible in the distance, creating a serene backdrop against the calm waters of the bay.

Guesthouse in Annan

4.84 out of 5 average rating, 121 reviews

Lakeview Loft with Hot Tub on Irish Mountain

Have a quiet getaway at the charming Cabin Loft Suite and enjoy the tranquility and serenity of Irish Mountain as you take in the fresh country air and breathtaking views of Georgian Bay and the Blue Mountains in the distance. Whether you are planning activities in the area or are looking for a place to relax, this space is for you. It is in an ideal location just outside the quaint town of Meaford and only a 30 minute drive from Blue Mountain.

Top guest favorite

A charming porch area is depicted, featuring a macramé swing chair hung beside a white door. The door displays textured glass panels and is complemented by a black wall lantern. Warm wooden decking enhances the inviting entrance.

Guest suite in Meaford

4.94 out of 5 average rating, 296 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!