Vacation rentals with a kayak in Grey Highlands

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Top-rated kayak rentals in Grey Highlands

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Guest favorite

Rental unit in Meaford

4.95 out of 5 average rating, 339 reviews

Sunrise and Bayview with Kayaks & Bikes

🌊 Bright and inviting waterfront/view ground level apartment in the heart of Meaford. 👋Entire apartment to yourself 👥Ideal for a romantic getaway 🏔20 minute drive to Blue Mountain attractions. 2 hours from Bruce Peninsula National Park 🏖 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

Guest favorite

Cottage in Severn Bridge

5 out of 5 average rating, 102 reviews

SunsetBayCottage Year Round HotTub!

Cozy Lakefront Cottage located on Sparrow Lake is the idea of relaxation. Enjoy the stunning sunsets while lounging on the large deck with a beverage in hand. The loons singing in the background. Perfect to enjoy with the whole family or on a couples retreat. The area is perfect for boating, fishing, walking, and biking around the neighbourhood. A mini toboggan hill Sparrow Lake is part of the Trent-Severn Waterway and you can boat to either Georgian Bay or Lake Couchiching in a few hours

Guest favorite

Guesthouse in Kemble

4.84 out of 5 average rating, 159 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.

Guest favorite

Condo in Innisfil

5 out of 5 average rating, 114 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 139 reviews

#TheFridayFlat: Winter Wonderland Charming Condo

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake. Come experience the ultimate waterfront getaway at Friday Harbour!

Guest favorite

Chalet in Gravenhurst

4.93 out of 5 average rating, 218 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

Guest favorite

Cottage in Meaford

4.9 out of 5 average rating, 199 reviews

Water's Edge - 4 Season Cottage

Comfy & cozy 3 bedroom year round cottage on the shores of Georgian Bay. Sleeps 6, washer/dryer, full kitchen w/dishwasher, living & dining w/fireplace, A/C, deck, BBQ, firepit & hot tub. Suits families with older children & couples. Lots of shopping, live entertainment, artisans & exquisite local fare. 30 min drive to Blue Mountain Village & the Spa. Close to the Bruce & Georgian Trails. Spectacular views of The Bay, The Blue Mountains and the best sunrises with your morning coffee.

Guest favorite

Cabin in Owen Sound

4.97 out of 5 average rating, 245 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.

Superhost

Cottage in Tiny

4.88 out of 5 average rating, 105 reviews

The Lakeview cottage w/ hot tub

Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Guest favorite

Bungalow in Georgian Bluffs

4.98 out of 5 average rating, 125 reviews

A Naturalist's Paradise - Shepard Lake waterfront

FALL RATES: enjoy the fall colours, 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. 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.

Guest favorite

Cabin in Lion's Head

4.91 out of 5 average rating, 198 reviews

Little Lake Lookout: Beach, Sauna, Dock, Dogs!

Escape to Little Lake Lookout! This serene 2-bedroom + loft and 2-bath retreat boasts 170ft of private lakefront on Little Lake. Enjoy stunning views of the Niagara Escarpment and an abundance of nature and wildlife. With all-season amenities and a scenic drive from the GTA and London, this dog-friendly oasis (we're fenced!) is the perfect getaway for making memories. Only 7 minutes from the charming village of Lion's Head. Book now for a truly unique experience! @LittleLakeLookout

Guest favorite

Cottage in Wiarton

4.98 out of 5 average rating, 107 reviews

Waterfront Cottage by Bruce Trail

Welcome to this stunning waterfront , cozy ,4 season cottage located on the edge of a cliff surrounded by the lake on one side and Bruce trail on the other. This private oasis is perfect for couples or families w. older kids where you can connect to nature but still stay close to the city. Walking distance to Bruce trail, short drive to Sauble Beach or Wiarton for shopping and dining, 25 min drive to Lions Head, 45 min to Tobermory. It's time to plan your visit to Bruce!!!