Guesthouse vacation rentals in Greater Toronto and Hamilton Area

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Greater Toronto and Hamilton Area

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Orangeville, Canada

4.95 out of 5 average rating, 310 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.

Oct 12 – 19

$136 per night

Guest favorite

Guesthouse in Aurora

4.92 out of 5 average rating, 115 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

Jul 17 – 24

$79 per night

Guest favorite

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

May 24 – 31

$66 per night

Guest favorite

Guesthouse in Campden, Canada

4.98 out of 5 average rating, 368 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.

Nov 13 – 20

$84 per night

Guest favorite

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!

May 25 – Jun 1

$71 per night

Guest favorite

Guesthouse in Acton

4.97 out of 5 average rating, 233 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.

Jul 2 – 9

$239 per night

Guest favorite

Guesthouse in Lincoln

4.97 out of 5 average rating, 101 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)

Oct 31 – Nov 7

$72 per night

Guest favorite

Guesthouse in Saint Anns

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.

Sep 15 – 22

$161 per night

Guest favorite

Guesthouse in Kawartha Lakes

4.92 out of 5 average rating, 248 reviews

The Loft on Sturgeon Lake

Enjoy the lakeside lifestyle on Sturgeon Lake! This beautiful custom loft features one spacious bedroom with a queen bed and large, bright windows. The suite has a private washroom with a large walk-in shower. There is a full kitchen available and living space with a pull out couch. Experience stunning sunsets over Sturgeon Lake from your private balcony or by the lake at the dockside fire pit. There is an outdoor pool that can be used when available and canoes and kayaks.

Oct 17 – 24

$120 per night

Guest favorite

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.

Apr 4 – 11

$118 per night

Superhost

Guesthouse in Newcastle, Canada

4.9 out of 5 average rating, 258 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"

Sep 19 – 26

$57 per night

Guest favorite

Guesthouse in Schomberg

4.93 out of 5 average rating, 345 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

Jun 3 – 8

$101 per night