Guesthouse holiday rentals in Greater Toronto and Hamilton Area

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Greater Toronto and Hamilton Area

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Aurora

4.92 out of 5 average rating, 114 reviews

Adorable Guesthouse Apartment With Free Parking

This beautiful brand new suite offers, Separate private guesthouse with vaulted ceilings & heated floors throughout. Private bathroom with standing shower. Queen loft bed & pull out couch. Flat screen smart TV. Kitchenette which includes: Fridge, cooktop & cookware, toaster oven, kettle, coffee maker. Live edge walnut table with 2 stools. Free wifi. 1 Free parking space. Close to Go Train. Fresh bed sheets & towels are provided. Phone charger and blue tooth speaker. Instagram @blueheronloft

Guest favourite

Guesthouse in Orangeville, Canada

4.95 out of 5 average rating, 311 reviews

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.

Guest favourite

Guesthouse in Uxbridge

4.96 out of 5 average rating, 100 reviews

Private Guesthouse in Nature minutes to Trails

Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Guest favourite

Guesthouse in Hamilton

4.83 out of 5 average rating, 185 reviews

Hamilton Beach Guesthouse with guest Kayaks

LAKEFRONT* renovated lakefront small cottage with two Kayaks situated on the Hamilton Waterfront beach trail. Enjoy fantastic views of the Toronto Skyline and secluded sandy beach. Relax on large deck, overlooking the lake. Right on the waterfront trail, roller blade, bike, kayak or enjoy the sandy beach. Very central for a Niagara winery and Toronto trip. Includes: Smart TV, 1 Parking spot, Tetherball, good Wi-Fi, Fire-pit , BBQ, Kayaks Queen size bed Coffee, condiments &cooking ingredients

Guest favourite

Guesthouse in Campden, Canada

4.98 out of 5 average rating, 369 reviews

Detached 450 sf cottage

This private detached cottage is located in the hamlet of Campden in Niagara's wine country. The cottage has one Queen bed located in a bedroom separated from the main area by a curtain and also one pull-out sofa located in the living area. Located on top of the Beamsville Bench minutes from Jordan Village & Balls Falls. Drive, bike, or walk to wineries such as Vineland Estates (2.6 km), Vienni (1.3 km), Tawse (2.6 km) & many others. about a 30 minute drive to NOTL wineries and Niagara Falls.

Guest favourite

Guesthouse in Angus

4.98 out of 5 average rating, 140 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to your private oasis! Our 600 sq/ft bachelor suite offers a clean and cozy retreat. Relax and unwind in the hot tub or with WIFI, Netflix & Prime TV. Just a 2-min drive to restaurants and groceries. CFB Borden & the North Trillium Trail within 5-min. Looking for more R&R? Discover 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. Book now for your ultimate getaway!

Guest favourite

Guesthouse in Acton, Canada

4.97 out of 5 average rating, 234 reviews

Wooden guesthouse in the forest

The guesthouse is the perfect getaway. Like living at a cottage, minutes away from the city. This loft guest house is fully equipped with a bedroom, own kitchen, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. Ten Minutes To 401. This retreat is nestled on a hill with spectacular views, surrounded by 16 acres of towering trees overlooking a creek with a private waterfall and walking trails. Perfect for photographers and influencers.

Guest favourite

Guesthouse in Lincoln, Canada

4.97 out of 5 average rating, 103 reviews

Dancing Fields on Tintern

Opened in august 2021, this Country setting loft in wine country - is surrounded by fields and close to local scenic Ball's Falls and golf courses. Minutes from numerous wineries and five minute drive from the Bench. Unique open concept space created with timeless features with touches of modern charm. Perfect for long week get away, 1 hour away from the hustle and bustle of (Toronto) city life, 25 minutes from Niagara falls/Niagara on the Lake - 1 hour from the US border (Buffalo)

Guest favourite

Guesthouse in Saint Anns, Canada

4.98 out of 5 average rating, 161 reviews

The Carriage House @ Mingle Hill

A country oasis on an Organic Lavender & Herb farm located on the Beamsville Bench, in the heart of Niagara wine country. We are within minutes of 40+ wineries and the finest food in Ontario. Relax, have a glass of wine on your private deck. Enjoy a morning coffee on the beautiful garden terrace, or exploring our farm. Have fun hiking the Bruce Trail or visiting one of Niagara's many attractions. We are approx. 40 min to picturesque Niagara-on-the-Lake and 30 min to Niagara Falls.

Guest favourite

Guesthouse in Newmarket, Canada

4.94 out of 5 average rating, 125 reviews

Stylish 1-Bedroom Home in the heart of Newmarket

This recently renovated unit is located walking distance from Newmarket's GO-Train, public transit, regional hospital, and Historic Main St strip. With its central location you are steps away from nature walks, hiking trails, lovely shops, great restaurants and excellent local craft breweries. Not to mention Upper Canada Mall. Nestled on a quaint street, and sitting on a half acre lot filled with old growth trees this place gives off serious cottage vibes. (But with better Wifi)

Guest favourite

Guesthouse in Saint Catharines, Canada

4.98 out of 5 average rating, 377 reviews

Private Estate Coachhouse + Hot Tub near NOTL!

Villa Niagara & it's private coach house - one of the oldest farm estate properties in the area close to Lake Ontario - the farmland has long been exchanged for housing but the charming original farm home and coach house remain. You'll be just a short stroll to the Welland Canal and the start of Niagara-on-the-Lake. Once you cross the Lock 1 bridge, you're instantly into farmland and wineries. Extreme care taken to thoroughly cleaned and disinfected between each stay.

Superhost

Guesthouse in Newcastle, Canada

4.9 out of 5 average rating, 259 reviews

Waterside Nature Cabin - Private & Comfortable

Spring-fed lake, 91 acres, trails, max privacy, solar power, heat, gas stove, cooler, clean out-house, wi-fi, firepit, 2SLGBTQ Pets ok To keep your costs low; No Cleaning Fees! You must clean up ALL personal mess & litter basic kitchen utensils, dishes, pots, pans provided bring bed sheet, pillow, blanket & drinking water Take all Garbage & Recycling back home with you when leaving Try to "leave the cabin, and the property better than you found it"