Guesthouse vacation rentals in Grey Highlands

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to Centre Street Studio! Our 600 sq/ft bachelor suite offers a private, clean and cozy retreat. Enjoy access to a private 2 person hot tub and/or explore our local trail system. Beautiful Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. A 2-min drive to town amenities. NOTE: We don't host guests new to AirBNB or who have no previous reviews attached to their profile.

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.

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

BnB Cabin at Dragonfly Ridge in Beaver Valley

Take in stunning panoramic views of Beaver Valley at Dragonfly Ridge. Close to many ski hills, hiking trailheads & river access points for paddling. Wake up to breathtaking views from your cozy, private cabin with a King Bed and Queen Bed in the loft. Book the Clubhouse ($40/hour, 2 hour minimum) to access a separate recreation building on the property with an 8-person cedar sauna, 6-person hot tub, cold plunge, a professional golf simulator, private movie theater, Ping Pong and more.

Cozy, quiet, clean cabin with wi-fi and fire pit.

Welcome to Penny Creek. A simple cabin just south of Durham. A private location surrounded by ponds, streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants, grocery, lcbo, fuel, coffee and shopping . An open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby. Easy access to ofsc (snowmobile) trails!

Hillside Studio: Midland + Winter Escape

Welcome to the Hillside Studio — a bright 900 sq.ft. 1-bedroom guesthouse in the heart of Midland. Perched on a hill, the Studio offers a modern, clean, airy retreat for 1–2 guests. It’s the ideal home base for your winter adventures around Southern Georgian Bay: • 10-min walk to Midland’s Downtown and the Curling Club • 10-min drive to Mountainview Ski Centre • 20-min drive to Awenda Provincial Park • 30-min drive to Moonstone, Horseshoe, Vetta Spa, and Quayle’s Brewery

Bright & Cozy 2BR Retreat Near Downtown and Nature

Welcome to a cozy, quiet 2-bedroom retreat designed for comfort and easy living. Enjoy a peaceful space with warm furnishings, comfortable beds, and a fully equipped kitchen—perfect after a day downtown, on nearby forest trails, or commuting for work or hospital visits. Minutes from downtown with quick highway access, free parking, and a calm neighbourhood, this home is ideal for couples, small families, and professionals year-round. This flat is not wheelchair accessible.

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

The Coach House at Belvedere Farm

A peaceful, retreat in the heart of Meaford, situated on twenty-four beautiful acres, surrounded by mature trees, trails, orchards and stunning views, yet only three mins to downtown with the ever popular Meaford Hall, restaurants, shops, harbour, library and so much more. Water access is also very close by. Bring your water toys in summer, and your snow toys in winter! Our place is not suited for children under 10 so please consider that when requesting.