Cottage vacation rentals in Southampton

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Top-rated cottage rentals in Southampton

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Guest favorite

Cottage in Pike Bay

4.99 out of 5 average rating, 104 reviews

Red Sky Lakehouse - Waterfront Oasis On Lake Huron

Rejuvenate at Red Sky, a spectacular waterfront cottage on the shores of Lake Huron in the remarkable Bruce Peninsula. Whatever your style of vacation, you’ll find it here. Come experience privacy, shallow warm waters & world-renowned sunsets all from the comfort of this private oasis. Or, use Red Sky as a home base to explore the national parks, sand beaches & legendary hiking & ski trails of the peninsula, all within a 30min drive. Truly Canadian cottage country at its best in all four seasons

Guest favorite

Cottage in Tobermory

4.93 out of 5 average rating, 327 reviews

The Water’s Edge

Enjoy this newly renovated waterfront home along the shore of Lake Huron! This beautiful 3 bedroom accomodation is located within 15 min to all main attractions including: the Grotto, Singing Sands beach, shopping, dining, Blue Heron and Glass Bottom boat cruises. Enjoy a ride on the Chi-Cheemaun, travel to the world’s largest fresh water island (Manitoulin Island). The beautiful scenery of the Niagara Escarpment, Fathom Five National Marine Park and more can be seen along the 1h 45min crossing.

Guest favorite

Cottage in Lion's Head

4.94 out of 5 average rating, 155 reviews

Trails End Family Friendly Beach House

🍂 See the colours of fall! Welcome couples and families to our cozy cottage in the quiet village of Lion's Head. Open year round. One street up from the beautiful sandy beach and playground. A fully stocked kitchen, fresh linens, spotless kitchen and bathroom, BBQ, and large front deck. Campfire pit and dark skies for stargazing. Restaurants and shopping are all within a minute's walk. Great hiking trails nearby along the Bruce Trail. Complimentary wine. <40 mins from the Grotto & Sauble beach.

Guest favorite

Cottage in Sauble Beach

4.96 out of 5 average rating, 109 reviews

COMPLETELY RENOVATED cottage -steps from the Beach

Charming coastal cottage, 2 min walk to the beach and 5 to the main strip. This is a perfect beachside retreat, with new flooring throughout, plank ceilings, fully loaded kitchen with SS appliances and quartz countertops, new bathroom, new mattresses... a large fully furnished patio and fire pit. 2.5 hours outside of TO on the shores of Lake Huron - and fully winterized for year-round getaways! AS SEEN IN HOUSE AND HOME MAGAZINE, JULY 2019! FOLLOW US: @amabelbeachhouse * linens not provided

Guest favorite

Cottage in Meaford

4.93 out of 5 average rating, 155 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

Cottage in Blyth

4.97 out of 5 average rating, 266 reviews

Up The Creek A-Frame Cottage

Relax in an A-frame Cottage over looking a stocked trout pond surrounded by trees. 20 acres of trails. Fish swim, kayak or canoe in the pond or creek. Watch the ducks, frogs, herons, birds, turtles & a variety of wildlife. Enjoy the stars & roast marshmallows at the camp fire. Fully stocked kitchen, BBQ, wood stove, fire pit and 3 piece bathroom. Wood and linens supplied. Ninja course, water mat & trampoline for your use. Groups welcome, extend your group send your request for more info.

Guest favorite

Cottage in Northern Bruce Peninsula

4.94 out of 5 average rating, 186 reviews

Glamping Cabin Nature Retreat

License #STA-2024-59 4 PEOPLE MAXIMUM. Best suited for Families and Couples. Quiet Neighbourhood- no parties/loud noise This cute &cozy “glamping” cottage is located in beautiful Miller Lake and within walking distance to Lake Huron access. Sleeping 4 people this small space comes with all the comforts needed for an amazing, quiet and cozy holiday! Unwind and decompress from the stresses of busy lives with the sounds of nature and the simpler joys of life at this “unplugged” cottage

Guest favorite

Cottage in Southampton

4.98 out of 5 average rating, 103 reviews

Beach House Cottage with Hot Tub

Welcome to JC's Cottage! This modern home embraces a beach house aesthetic providing ultimate comfort for your getaway. This 2-bedroom home located all on one floor has a huge backyard, patio with bbq, and hot tub for fun and relaxation. Enclosed with a double garage with an extra fridge, tv , games table. Plenty of space for bikes, kayaks and canoes. The house is walking distance to shops, bars and local restaurants. Walk to the beach at the end of the street for world famous sunsets.

Guest favorite

Cottage in Meaford

4.91 out of 5 average rating, 198 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.

Superhost

Cottage in Kemble

4.81 out of 5 average rating, 134 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.

Guest favorite

Cottage in Elmwood

4.98 out of 5 average rating, 126 reviews

Little Red Cabin on the River

Bright and cozy, open concept cabin retreat overlooking Styx river in beautiful West Grey. Relax next to a quiet river on a large lot with elevated deck, natural wood-burning fire pit and BBQ. This all season get away is 2 hours from Toronto, perfect for small families or a small group. Recently updated, this cabin features simple, modern decor with a fully furnished kitchen for home cooked meals and baking. Also now includes WiFi and an outside wood burning, cedar barrel sauna.

Guest favorite

Cottage in Wiarton

4.94 out of 5 average rating, 184 reviews

Nature Lover’s Paradise

Relax in nature & style at our modern cottage. 10 min drive to Sauble Beach main strip. Enjoy panoramic views & breathtaking sunsets overlooking Lake Huron. Walk or drive to many beautiful beaches. Very peaceful area. Great place for family getaways. Fully equipped kitchen. Comfortable furniture. A/C in main areas. Campfire & kids playground. Max 8 adults or 12 people for families. Please note: 1) Bed lines & towels not included; 2) Guests are responsible for garbage disposal.