Vacation rentals in Annan

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Top-rated vacation rentals in Annan

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Guest favorite

Guest suite in Chatsworth

4.85 out of 5 average rating, 349 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

May 23 – 30

€ 108 per night

Superhost

Cottage in Meaford

4.93 out of 5 average rating, 134 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.

Sep 18 – 25

€ 298 per night

Guest favorite

Apartment in Owen Sound

4.92 out of 5 average rating, 155 reviews

Charming Renovated Century Home-close to all!

This beautiful 3 bedroom, 1,800 sq ft apartment was completely renovated from top to bottom in summer of 2019! Only 45 minutes from the top of Blue Mountain, 1 hour and 15 minutes to the tip of Tobermory and the famous Grotto at the Bruce Peninsula National Park! This gorgeous home is very centrally located in Owen Sound, this area features extremely scenic hiking trails, such as the Bruce Trail and many others. Whether for business or pleasure, this private home is certain to suit your needs.

Sep 30 – Oct 7

€ 136 per night

Guest favorite

Apartment in Meaford

4.96 out of 5 average rating, 272 reviews

Sunrise and Bayview with Kayaks & Bikes

🌊 Bright and inviting waterfront/view ground level apartment in the heart of Meaford. 👥Ideal for a romantic getaway 🏔20 minute drive to Blue Mountain attractions. 2 hours from Bruce Peninsula National Park Golfing Close by 🏖 5 minute stroll to the Harbour and Sandy Beach or a pebble beach right across the road ! 🚶‍♂️Walking distance to Meaford Hall 🍽Dining options a block away:) Kayaks, Bikes, Floaties, snowshoes and snorkels are complimentary. Come and discover our gem of a town.

Nov 15 – 22

€ 122 per night

Guest favorite

Guesthouse in Kemble

4.82 out of 5 average rating, 132 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

€ 98 per night

Guest favorite

Cabin in Owen Sound

4.97 out of 5 average rating, 226 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.

May 6 – 13

€ 137 per night

Superhost

Tiny home in Meaford

4.85 out of 5 average rating, 254 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 pool available for the summer months with possibilities of covid restrictions. INTERNET just upgraded!

Feb 15 – 22

€ 97 per night

Guest favorite

Guest suite in Holland Centre

4.97 out of 5 average rating, 193 reviews

Dragonfly Hollow bnb

Nature lovers, Come experience the natural beauty of the Grey-Bruce region. Our home is in a very quite natural setting surrounded by trees. In summer explore the many lakes, beach or waterfalls . Hike the Bruce trail, or one of many others; good for ATVing, Scenic Motorcycle Routes. Fall is especially beautiful, the hills and valleys fill with vibrant colours. In winter, enjoy cross-country, downhill skiing, snowboarding, skidooing. Blue Mountain only a Scenic 40 mins away.

Nov 28 – Dec 5

€ 87 per night

Guest favorite

Apartment in Meaford

4.98 out of 5 average rating, 291 reviews

Fuller House Airbnb

Steps from Georgian Bay and beach. This newly renovated 400 sq/ft walk out, self-contained apartment is located on a quiet double lot, offering privacy and a beautiful natural setting. Enjoy the comfort of a substantial continental breakfast, homemade baking and more in your cozy kitchenette, or outdoor seating areas. Apartment includes microwave, coffee maker, toaster, kettle and kitchenware. BBQ provided on site. Front of home is owners' living space and Art Studio/Gallery.

May 31 – Jun 7

€ 80 per night

Guest favorite

Home in Annan

5.0 out of 5 average rating, 44 reviews

River's Edge Retreat

The River's Edge Retreat is a newly renovated four season cottage in the village of Leith on the Bothwell's river and Georgian Bay , Ontario. 2 Hours north of Toronto Only 10 minutes to Owen Sound. The cottage is a short walk to three public beaches to enjoy swimmming and beautiful sunsets. Grey Sauble Conservation Area and The Bruce Trail for all season activities such as hiking,snowshoeing and cross country skiing Owner has Yoga studio next door classes available.

Feb 21 – 28

€ 186 per night

Guest favorite

Guest suite in Meaford

4.95 out of 5 average rating, 167 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!

Sep 9 – 16

€ 135 per night

Guest favorite

Cabin in Owen Sound

4.87 out of 5 average rating, 305 reviews

Heritage Reflections Guest House

Our place is perfect for someone looking for quiet, private place for a getaway. It is close to the Bruce Trail for hiking and Sauble Beach. We also are close to the Georgian Bluffs rail trail for cycling and hiking. Our guest house is great for couples, solo adventurers, and business travelers. We are a rural property with extensive gardens that you are welcome to explore and enjoy.

Jun 2 – 9

€ 98 per night