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Guesthouse holiday rentals in Greater Toronto and Hamilton Area

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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
The inviting living area features warm wood accents and a cozy seating arrangement. A brick fireplace stands as a focal point, complemented by large windows that flood the space with natural light. Ferns add a touch of greenery, enhancing the relaxing atmosphere.
Guesthouse in Uxbridge

Cabin in nature Close to trails and Thermea Spa

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 ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

FamilyValueAmenities

4.93 out of 5 average rating, 193 reviews
Top Guest favourite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville

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.

ValueLocationWi-Fi

4.96 out of 5 average rating, 404 reviews
Top Guest favourite
A modern living space is highlighted by a spacious bed and an entertainment area featuring a large wall-mounted TV. A cozy seating arrangement includes a soft couch and a stylish armchair. Ambient lighting is provided by a chandelier above, complemented by a decorative fire feature.
Guesthouse in Pickering

Luxury Ground-Level "Suite Escape"

"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

ValueLocationAccess

4.95 out of 5 average rating, 131 reviews
Top Guest favourite
A doorway opens to a private deck featuring two wooden chairs with white cushions and a small table between them. The view showcases lush greenery and rolling farmland, under a clear sky.
Guesthouse in Lincoln

Little Blue Barn on the Bench

Beautifully situated in the heart of Niagara's wine country and minutes away from the Bruce trail and other hiking favourites, our guest house boasts peaceful views of rolling farmland. Built on top of a barn-style workshop, this private and peaceful studio space is the perfect Niagara getaway for a couple or an individual. Come catch a stunning sunset on your own private deck while you sip a glass of wine or enjoy a coffee. Other perks for your enjoyment: king size bed and out door firepit.

ValueLocationBeach

4.95 out of 5 average rating, 245 reviews
Guest favourite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS SEPTEMBER 1 (1 night/2 days) SEPT 7-11 OCTOBER 18-21 (3 nights) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards & direct Lakefront

LocationFamilyNearby

4.96 out of 5 average rating, 329 reviews
Guest favourite
A spacious sleeping area features a queen bed with crisp white linens, a sleek dresser, and a work desk with a chair. A decorative vase of roses adds a touch of color. Natural light enters through the glass doors leading to the patio.
Guesthouse in Richmond Hill

Balcony House with Separate Entrance，free Parking

Enjoy the glamour of this spacious, stylish, worry free, upscale place. It is brand new and located in the Heart of Richmond Hill, walking distance from David Dunlap Observatory Park, Plazas, Malls, Schools, Restaurants and Supermarkets. Close To Highway And Go Station, Viva, Yrt. Separate entrance and all inclusive with 1 queen bed, 1 double Sofabed if more than 2 guests, 65in smart TV, high speed wifi. Micro oven, Fridge, K-cup coffee machine, full bathroom, patio sittings, 1 free parking

LocationValueWi-Fi

4.93 out of 5 average rating, 192 reviews
Top Guest favourite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie

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.

ValueFamilyComfort

5.0 out of 5 average rating, 307 reviews
Superhost
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Mississauga

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

LocationValueView

4.89 out of 5 average rating, 114 reviews
Top Guest favourite
Guesthouse in St. Catharines

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.

ValueFamilyBiking

4.99 out of 5 average rating, 477 reviews
Top Guest favourite
The entrance displays a well-crafted wooden door, flanked by textured stone walls. A hanging planter filled with vibrant flowers is positioned beside the door, complemented by lush green foliage at the base. A welcome mat lies on the ground, inviting guests into the space.
Guesthouse in Morriston

Country Getaway Guest Loft Sleeps 5 people

Relax in this peaceful 2 bedroom 2-bed place in a country setting. Located a few minutes south of Guelph with easy access to the 401. Pearson Airport, Hamilton, Milton, Mississauga, and Kitchener Waterloo are all within 35 minutes. Stroll down the country lane or a nearby trail. Check out a local restaurant – Bistro Reunion, The Danish Place, Change of Pace, Sleemans Brewery, or figure out who did it at the Aberfoyle Mill murder mystery dinner - all within 15 minutes!

ValueLocationSleep quality

4.95 out of 5 average rating, 125 reviews
Top Guest favourite
An open living area features a cozy seating arrangement with a blue couch and a rustic wooden island. A spiral staircase ascends to the loft above. Large windows provide natural light, while a wall-mounted TV and a pellet stove enhance the space.
Guesthouse in Port Perry

Port Perry Island Krazee Acres Hobby Farm

Krazee Acres! Private 8-acre hobby farm a short walk to Lake Scugog, with Farm Fresh smells! Rustic Boho accents, Relaxing Soaker tub, walk-in shower, fully equipped kitchen, pellet stove, and air conditioning. Enjoy outdoor wood fires, sunsets and stars year-round. Free Parking for cars, trailers, boats. Large patio. BBQ provided. 3KM to the Great Blue Heron Casino, minutes to Historic Downtown Port Perry. Close to trails and Marina/Restaurant, (Seasonal). Relax

LocationFamilyWi-Fi

4.95 out of 5 average rating, 133 reviews
Guest favourite
The living area features a comfortable seating arrangement with a large couch and a wooden coffee table. A television is positioned across from the seating, while a decorative ladder shelf adds a touch of style. Adjacent dining space is visible in the background.
Guesthouse in Niagara-on-the-Lake

On the Vineyard @ 1068, Niagara on the Lake

Nestled in the heart of Niagara's wine country, On the Vineyard @1068 offers a peaceful retreat where comfort meets charm. Whether you are here for a weekend escape or a longer stay, our property offers all the amenities you need to feel at ease and make yourself at home or whether you're here to sip your way through the local vineyards, explore the scenic beauty of the region, enjoy a round or golf or simply unwind, you've found the perfect place to do it all.

LocationValueTV

4.93 out of 5 average rating, 391 reviews

Popular amenities for Greater Toronto and Hamilton Area guesthouses

KitchenWifiPoolFree parking on premisesAir conditioning

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Guelph

Sweet Studio ~ Spacious Yard ~ Nature Haven ~ AC

ValueLocationAccuracy

4.91 out of 5 average rating, 625 reviews
Top Guest favourite
A private detached cottage is featured with a clean white exterior and a modern metal roof. The entrance is framed by a wooden fence, enhancing privacy. Nearby foliage and outdoor seating under a shaded umbrella contribute to a serene outdoor setting.
Guesthouse in Campden

Detached 450 sf cottage

FamilyLocationBathroom

4.98 out of 5 average rating, 467 reviews
Guest favourite
A rustic cabin is nestled in a vast field, surrounded by vibrant autumn foliage. The warm-toned structure contrasts with the lush greenery and colorful trees, while the expansive sky adds depth to the serene landscape.
Guesthouse in Newcastle

Bee Keeper's Cabin - a very private retreat

LocationValueDecor

4.89 out of 5 average rating, 250 reviews
Top Guest favourite
Guesthouse in Breslau

House on the Hill

FamilyValueComfort

4.97 out of 5 average rating, 225 reviews
Top Guest favourite
A vibrant sunflower garden showcases tall, bright yellow blooms surrounded by lush green leaves. In the background, a serene landscape is visible. The figure stands among the flowers, partially obscured by the sunflowers, creating a peaceful outdoor scene.
Guesthouse in Saint Anns

The Carriage House in the heart of Wine Country

FamilyValueQuiet

4.98 out of 5 average rating, 227 reviews
Top Guest favourite
Guesthouse in St. Catharines

Lakeshore Loft-quiet and comfortable 1 bedroom apt

ValueLocationDecor

4.95 out of 5 average rating, 150 reviews
Top Guest favourite
A modern treehouse-style guesthouse is elevated on stilts, surrounded by lush greenery and towering trees. A stone pathway leads toward the entrance, while large glass windows allow natural light to flow into the interior, blending the structure harmoniously with the forest setting.
Guesthouse in Action

Treehouse in the forest

FamilyValueGetting around

4.96 out of 5 average rating, 341 reviews
Top Guest favourite
An aerial view captures a guesthouse surrounded by lush greenery. A large pool glistens in the sun, accompanied by lounge chairs nearby. The spacious backyard is enhanced by a fire pit area and shaded patio, providing ample outdoor space for relaxation.
Guesthouse in Elora-Salem

The Blue Lagoon | Pool & Coastal Tinyhome

LocationValueWalkability

4.97 out of 5 average rating, 202 reviews

Guesthouses with a patio

Top Guest favourite
A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.
Guesthouse in Erin

The Captain's Cottage at Willow Pond

LocationFamilyAccuracy

4.96 out of 5 average rating, 153 reviews
Top Guest favourite
An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.
Guesthouse in Barrie

Chalet w/ yard & pool, walk to beach & playground

FamilyValueGetting around

4.98 out of 5 average rating, 104 reviews
Top Guest favourite
A modern electric fireplace is framed by a light-toned mantel. A flat-screen TV is mounted above, while a basket and two wine glasses are placed on the mantel. Decorative dried plants are arranged in a ceramic planter nearby, all set against a neutral wall.
Guesthouse in Elora-Salem

Melville Guesthouse

FamilyValueCondition

4.99 out of 5 average rating, 134 reviews
Top Guest favourite
Guesthouse in Elora-Salem

Tiny Home retreat in quiet neighbourhood

FamilyValueHeating

4.97 out of 5 average rating, 115 reviews
Top Guest favourite
The exterior of the historic carriage house features stone and board & batten siding, surrounded by lush greenery. Two red chairs sit on a gravel area in front of the building, inviting relaxation. A set of stairs leads to the entrance of the upper level.
Guesthouse in Elora-Salem

Carriage House - Elora

FamilyValueDecor

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
A serene bedroom features a spacious bed adorned with light bedding and decorative pillows. Natural light streams through a window, illuminating the room's soft, neutral tones. A cozy armchair and hanging plant add a touch of greenery and elegance to the inviting space.
Guesthouse in Hamilton

Boutique coach house with Scandinavian Steam Sauna

FamilyLocationBiking

5.0 out of 5 average rating, 206 reviews
Guest favourite
A spacious living area is furnished with a modern gray sofa and a white TV unit, which holds a flat-screen TV. Natural light enters through sliding glass doors leading to a balcony. In the background, a kitchen with white cabinetry and a dining area is visible.
Guesthouse in Richmond Hill

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

ValueFamilyCondition

4.94 out of 5 average rating, 160 reviews
Guest favourite
A private hot tub is situated on a wooden deck, its water gently bubbling. A tray displays a bottle of rosé and two glasses with lemon slices, alongside fresh flowers. Snow can be seen in the background, suggesting a cozy winter setting.
Guesthouse in Port Perry

No worries

LocationValueCheck-in

4.86 out of 5 average rating, 149 reviews

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Niagara Falls

Location! Location! Perfect spot

FamilyValueGetting around

4.89 out of 5 average rating, 189 reviews
Superhost
A spacious living area features a comfortable dark sectional sofa adorned with accent pillows. A coffee table with a decorative vase sits in front. Opposite, a flat-screen TV is positioned on a wooden stand, while a dining table with green chairs is visible in the background.
Guesthouse in Markham

2 bedroom Guest house in North of Toronto

FamilyLocationDecor

4.87 out of 5 average rating, 104 reviews
Guest favourite
Guesthouse in Barrie

Quiet 2BR Suite • Kitchen, Workspace + Parking

ValueLocationHospitality

4.87 out of 5 average rating, 135 reviews
Guest favourite
An open-concept living space features a cozy seating area with black leather sofas, a dining table, and a fully equipped kitchen. A spacious bed is positioned against the wall, with large windows providing natural light and views of the peaceful surroundings.
Guesthouse in Schomberg

Country Cabin Retreat | King Bed | Pet Friendly

FamilyLocationHospitality

4.93 out of 5 average rating, 513 reviews
Guest favourite
Guesthouse in Peterborough

Peterborough Zen Retreat

FamilyLocationSleep quality

4.88 out of 5 average rating, 143 reviews
Guest favourite
A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.
Guesthouse in Orangeville

A bright & stylish urban studio

LocationValueLayout

4.94 out of 5 average rating, 151 reviews
Top Guest favourite
Guesthouse in Collingwood

Cozy 3BR Collingwood Getaway | Hot Tub + Sauna

LocationFamilyPets

5.0 out of 5 average rating, 88 reviews
Top Guest favourite
A modern living area features a blue velvet sofa with decorative pillows, a sleek coffee table, and a dark fireplace. Natural light flows through large sliding glass doors, which open to a backyard. A leafy plant and a floral arrangement add touches of greenery.
Guesthouse in Toronto

Bright Mid-Mod Stay

LocationFamilyCheck-in

4.98 out of 5 average rating, 48 reviews

Destinations to explore