Vacation rentals in Annan

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Annan

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A waterfront patio features a dock extending into Georgian Bay, accompanied by several lounge chairs arranged for relaxation. An umbrella provides shade, enhancing the scenic view of the calm water and distant shore under a clear sky.

Home in Meaford

4.87 out of 5 average rating, 411 reviews

Waterfront* Hot Tub* - Beachhouse Hideaway *Unique

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Superhost

Home in Meaford

4.77 out of 5 average rating, 426 reviews

Serenity by Georgian Bay, 4 Season, escape!

This charming, cozy house offers serenity edge of town, by Georgian Bay! Suitable for couples, families and small groups. Across the street from the Bay. Comes with kayak, SUP and lawn games! Close to many Bruce Trails, Scenic Caves trails, or Georgian Trail, and golf. After a busy day exploring or playing, retreat to Meaford and either whip up something delicious in our fully equipped kitchen and dine in with a view of the bay, or walk down Sykes 5 min to one of Meaford's excellent restaurants.

Guest favorite

Two lounge chairs with a light-colored cushion are positioned on a stone patio overlooking Georgian Bay. The shoreline is lined with smooth, rounded stones, and plants are present in the foreground. The warm glow of the sunset reflects over the tranquil water surface.

Cottage in Meaford

4.93 out of 5 average rating, 176 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.

Guest favorite

A shared heated pool is surrounded by a spacious lawn, featuring lounge chairs and a gazebo for shade. The pool area is bordered by trees and is nestled in a countryside setting with a view of nearby fields.

Tiny home in Meaford

4.87 out of 5 average rating, 350 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. INTERNET just upgraded! Window Aircon/pool opens end of May or June.

Top guest favorite

Cottage in Southgate

4.98 out of 5 average rating, 111 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

The interior of the yurt is viewed from below, highlighting a circular skylight at the center. Colorful patterns adorn the wooden beams, and a metal flue extends downwards, blending traditional and modern elements in the design.

Yurt in Meaford

4.99 out of 5 average rating, 121 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.

Top guest favorite

Guest suite in Kimberley

4.96 out of 5 average rating, 226 reviews

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

Top guest favorite

A charming log cabin features a wooden porch framed by greenery. The stone chimney sits atop the roof, while windows allow light to filter into the interior. A stack of firewood is neatly arranged beside the entrance, enhancing the rustic appeal of the home.

Cabin in Owen Sound

4.96 out of 5 average rating, 255 reviews

Cozy 'Off the Grid" Rustic Cabin

If you enjoy 'roughing it', stay in our beautiful log home from the late 1800's. It has been completely redone, maintaining all of the old character. It is nestled in the edge of the bush, that provides kilometres of hiking trails. The cabin is also situated on a pond so you can spend your days swimming, canoeing, fishing and exploring this nature lover's paradise. Spend your time here unplugging from your everyday life and reconnecting to the healing properties of a natural environment.

Top guest favorite

A serene garden area is depicted, featuring a curved flowerbed lined with various colorful flowers and green plants. Two wooden chairs are positioned nearby, offering a tranquil spot for relaxation. Lush greenery and trees surround the space, enhancing its natural appeal.

Bungalow in Georgian Bluffs

4.98 out of 5 average rating, 128 reviews

A Naturalist's Paradise - Shepard Lake waterfront

Located on a tranquil, private, inland lake-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. Paddle boats are exclusive for your use. Enjoy fishing/bird watching. Close to hiking trails, golf courses & there are beautiful beaches for swimming just minutes away. Relax on the dock, read, BBQ & enjoy campfires.

Top guest favorite

A rustic wooden bridge is seen leading through lush greenery, with moss covering the path. Surrounding trees add to the natural ambiance, creating a tranquil passageway that invites exploration of the area beyond.

Apartment in Owen Sound

4.96 out of 5 average rating, 131 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

The expansive view captures the tranquil waters of Georgian Bay, framed by lush greenery and rugged hills. The clear blue sky complements the vibrant turquoise hues of the water, while distant sailboats add a sense of activity to the serene landscape.

Guesthouse in Annan

4.85 out of 5 average rating, 109 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.

Guest favorite

A sandy beach extends along a calm lake, bordered by smooth stones and framed by trees. Soft sunlight filters through the clouds, reflecting off the water's surface, creating a serene and inviting atmosphere.

Guest suite in Meaford

4.94 out of 5 average rating, 260 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!