
Guest house holiday rentals in Grey Highlands
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Grey Highlands
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

Newly Renovated 2 bdr basement
Newly renovated cozy 2 bdr basement apartment with a seperate entrance Very clean & peaceful space perfect for & short term stay Friendly neighborhood - parks, trails & amenities >Major intersection: Sandalwood & Hurontario * 10 mins to highway 410 * 2 mins walk to bus stop * 5 mins walk to amenities * 10 mins > downtown Brampton & train station * Free parking, self check in *Like hotel stay experience *High quality white beddings ● Verified ID ●No parties, pets, smoking, illegal activities

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.

Stunning Lakeside Loft Perched Above Georgian Bay
Architect-designed. Award-winning. Most unique property on The Bruce. Cozy, cool Lakeside Loft Guest House at Cameron Point. Open concept loft-style 2-storey Cabin and Bunky. Glass walls. Spectacular views of the water and bluffs! Summer: Loft + Bunky: 4 BR. Up to 8 guests from July 14. Extra fee for guests 5-8: $100/night pp Modern kitchen. 3-pce bath. Private entrance. Wifi. Winter: 2 BR. Base fee for up to 4 guests. Enjoy Bruce Trail hikes, swimming, kayaking. Chill by the fire!

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.

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!

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 Captain's Cottage at Willow Pond
You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Dreamers Studio Apartment, 3 Acre Wooded Property
Beautiful highly-rated studio apartment at back of 3 acre wooded property, Hwy6 Hepworth. Literary themed property, goats, a secret garden. You can self check-in & out. Studio has a kitchen, living area, TV & gas fireplace. Property connects to Northern Dunes Golf Club & is 5 min from Bruce Ski’s Nordic Centre. It's 1 min from Tim Hortons, 7 min from Sauble Beach, 10 from Wiarton & 20 min from Owen Sound. ALL backgrounds welcome. 420 friendly.
Popular amenities for guest house rentals in Grey Highlands
Family-friendly guest house rentals

Private & Detached Downtown Brampton Garden Suite

Forest Haven Guesthouse

Bright and Airy Guest Suite with Pool

Balcony House with Separate Entrance,free Parking

Studio Blue, tiny home retreat

Carriage House - Elora

Wrights Coach House -Visit the Village of Lights!

Melville Guesthouse
Guest house rentals with a patio

Mono Countryside Home & Farm

From A to Zen - a refined glamp

ManCave Made for a fun getaway!

Windfall Cottage On Little Lake

The Hideout

The Wind, Sky and Fire Escape

Island Lake Guest House

Adorable 1-bedroom guesthouse with gas fireplace.
Guest house rentals with a washing machine and dryer

Cozy Private Basement Bedroom with ensuite

Entire Guesthouse - Forest Retreat, Starlink WiFi

Country Experience

Bright & Modern Lower Level Apt in Keswick

The Coach House at Belvedere Farm

Garden Suite Getaway

Cozy Private 1-Bedroom Suite | Entire Apartment

Warm rustic luxury chalet near lake & skiing
Quick stats about guest house rentals in Grey Highlands

Total holiday rentals
Explore 10 holiday rentals in Grey Highlands

Nightly prices starting at
Grey Highlands holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 280 verified reviews to help you choose

Wifi availability
10 of Grey Highlands holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Grey Highlands rentals

4.9 Average rating
Grey Highlands stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Central New York Holiday rentals
- Cleveland Holiday rentals
- Ski-in/ski-out rentals Grey Highlands
- Flat rentals Grey Highlands
- Rentals with pools Grey Highlands
- Private suite rentals Grey Highlands
- Rentals with a firepit Grey Highlands
- Rentals with beach access Grey Highlands
- Rentals with a patio Grey Highlands
- Fitness-friendly rentals Grey Highlands
- Beachfront rentals Grey Highlands
- Rentals with a sauna Grey Highlands
- Loft rentals Grey Highlands
- Apartment rentals Grey Highlands
- Rentals with a washing machine and dryer Grey Highlands
- Rentals with a hot tub Grey Highlands
- Bed and breakfasts Grey Highlands
- Family-friendly rentals Grey Highlands
- House rentals Grey Highlands
- Rentals with a fireplace Grey Highlands
- Rentals with an EV charger Grey Highlands
- Cabin rentals Grey Highlands
- Rentals with outdoor seating Grey Highlands
- Rentals with breakfast Grey Highlands
- Rentals with a kayak Grey Highlands
- Smoking-friendly rentals Grey Highlands
- Rentals with lake access Grey Highlands
- Cottage rentals Grey Highlands
- Chalet rentals Grey Highlands
- Townhouse rentals Grey Highlands
- Pet-friendly rentals Grey Highlands
- Waterfront rentals Grey Highlands
- Guest house rentals Grey County
- Guest house rentals Ontario
- Guest house rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Wasaga Beach Area
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Elora Gorge
- Inglis Falls
- Scandinave Spa Blue Mountain
- Harrison Park
- Caledon Ski Club LTD
- Wye Marsh Wildlife Centre
- Forks of the Credit Provincial Park
- Mono Cliffs Provincial Park
- Awenda Provincial Park
- Sauble Beach
- Sunset Point Park
- Centennial Beach
- Elora Quarry Conservation Area
- Island Lake Conservation Area
- Innisfil Beach Park
- Sauble Falls Provincial Park
- Rockwood Conservation Area




