Guesthouse holiday rentals in Milton

4.96 out of 5 average rating, 341 reviews

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

Treehouse in the Forest is the perfect getaway. Like living at a cottage, minutes away from the city. This place is fully equipped with 2 bedrooms, own kitchenete, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. 10 Minutes to 401. This guesthouse 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.

FamilyValueGetting around

4.96 out of 5 average rating, 328 reviews

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

LocationValueSolo travel

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.

4.98 out of 5 average rating, 133 reviews

Melville Guesthouse

Welcome to The Melville Guesthouse, a charming one-bedroom retreat on a quiet street in Elora. Enjoy the privacy of your yard while being a short walk from downtown, the Elora Centre for the Arts, the river, and historic homes. Whether you’re here for trails, boutique shops, or Elora’s arts and dining scene, our standalone guesthouse offers comfort and convenience—perfect for couples and families, with a pull-out couch for extra guests. Ideally located, you’re near everything Elora offers.

LocationFamilyCondition

4.91 out of 5 average rating, 625 reviews

Guesthouse in Guelph

Sweet Studio ~ Spacious Yard ~ Nature Haven ~ AC

Experience a private, urban studio cottage located in a gorgeous tree-filled backyard in the Junction neighbourhood, close to downtown Guelph, with full amenities. Comfortable queen bed, natural gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, additional sleeping loft, private back flagstone patio, and one complimentary sauna. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

FamilyValueGetting around

Guesthouse in Mississauga

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.

4.89 out of 5 average rating, 114 reviews

“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”

ValueFamilyAccess

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.

5.0 out of 5 average rating, 206 reviews

Boutique coach house with Scandinavian Steam Sauna

Morwick Lane - a boutique retreat steps from Hamilton’s best downtown spots, and just an hour from Toronto and Niagara Falls. This restored coach house features curated comforts including a sleek fireplace, luxurious bedding, and a cedar Scandinavian sauna. Enjoy the garden shower after your steam sauna, then unwind in the courtyard with a fireplace and stunning gardens. Perfect for a romantic escape or solo wellness retreat, Morwick Lane invites you to experience something unforgettable.

LocationFamilyLayout

4.95 out of 5 average rating, 124 reviews

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!

ValueFamilyBathroom

Guesthouse in Halton Hills

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

4.92 out of 5 average rating, 193 reviews

The Clayhill Bunkie

Semi off-grid bunkie on The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, Glen Williams, Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views. This is NOT a hotel room.

ValueLocationGetting around

4.97 out of 5 average rating, 223 reviews

Guesthouse in Breslau

House on the Hill

What makes The House unique? How about: - a year-round heated indoor pool & sauna - private 2-bedroom + loft guesthouse with private entrance - fully-equipped kitchen - homey living area with electric fireplace - 27 gorgeous acres with 2 ponds - private patio & BBQ There's so much more! Come join your hosts Frances & Rod and experience a country retreat in the middle of the city... all this within 5km to Waterloo Int'nl Airport & 15 min to tri-cities & 401.

ValueFamilyPool

Guesthouse in Richmond Hill

The exterior of a newly constructed coach house is showcased, featuring a modern design with stone and brick elements. Two garage doors are visible, along with a front porch and balcony above. A well-maintained lawn and a young tree add greenery to the inviting entrance.

4.94 out of 5 average rating, 111 reviews

Entire 1 Bedroom Detached Coach House

This completely private and newly built (Dec 2023) independent one bedroom coach house is located in the prestigious Observatory Hill neighborhood in south Richmond Hill. Convenient location near transit, shops and restaurants (mins drive to Hwy 404 and Hwy 407). This unit also offers secure internet, Keurig coffee machine, TV, independent AC, furnace, laundry, private entrance with easy Smart Lock access and two free parking on the driveway and many more!

FamilyValueAir conditioning

4.87 out of 5 average rating, 232 reviews

The open-concept living area showcases a gray sofa paired with two elegant chairs featuring gold accents. A small, dark table is positioned between them. Natural light enters through a nearby window adorned with soft curtains, enhancing the inviting ambiance.

Guesthouse in Brantford

Charming Garden Guest House with Modern Comforts

Take it easy at this unique and tranquil getaway and enjoy a delightful stay in a separate studio garden suite for your Brantford trip. The guest house is equipped with AC, heating, and WIFI to make your stay comfortable. Our guest house is less than five minutes away from Hwy access, restaurants, bars, parks, and the Wayne Gretzky Sports Center. A great location for you to discover Brantford the best way. We look forward to hosting you!

LocationValueOutdoor spaces

4.98 out of 5 average rating, 226 reviews

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

Welcome to your relaxing escape on our organic flower and herb farm, nestled on the scenic Beamsville Bench. Unwind with a glass of local wine on your private deck, stroll through fragrant gardens, or explore the nearby Bruce Trail. Just minutes from 40+ wineries and top dining spots. Only 30 minutes to Niagara Falls and 45 to Niagara-on-the-Lake. A peaceful retreat perfect for nature lovers, wine enthusiasts, and romantic getaways.

LocationValueBiking

Popular amenities for Milton guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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.

4.97 out of 5 average rating, 202 reviews

The Blue Lagoon | Pool & Coastal Tinyhome

LocationFamilyBarbecue

4.85 out of 5 average rating, 221 reviews

Hamilton Beach Guesthouse with guest Kayaks

ValueLocationNearby

4.98 out of 5 average rating, 466 reviews

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

FamilyLocationIndoor spaces

4.77 out of 5 average rating, 362 reviews

Guesthouse in Brampton

Newly renovated & contemporary 2 Bdrm Basement Apt

ValueFamilyLaundry

5.0 out of 5 average rating, 121 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

ValueFamilyComfort

The exterior of a brick building is depicted, featuring a garage door and a pathway. A decorative light fixture is mounted above the entrance. Utility components, including a meter and drainage, are visually present alongside a yellow container. The setting is illuminated by soft evening light.

4.83 out of 5 average rating, 194 reviews

Independent Suite Near Airport 4 Guests 2 Qn. Beds

FamilyValueComfort

4.86 out of 5 average rating, 225 reviews

A modern kitchen features stainless steel appliances, including an oven and refrigerator. White cabinets provide ample storage, while a sleek countertop offers space for food preparation. A clear dining chair reflects the contemporary design, and a small vase with yellow flowers adds a touch of color.

Guesthouse in Brampton

Newly Renovated 2 bdr basement

ValueLocationParking

4.98 out of 5 average rating, 242 reviews

The exterior of a modern tiny home is depicted, featuring light-colored siding and large windows. A set of stairs leads to a welcoming deck, adorned with potted plants and two wooden chairs. An umbrella stands near the entrance, providing shade for outdoor relaxation.

Guesthouse in Toronto

Adorable, modern tiny home in Leslieville

ValueLocationBeach

Guesthouses with a patio

4.96 out of 5 average rating, 114 reviews

Tiny Home retreat in quiet neighbourhood

FamilyValueCheckout

4.95 out of 5 average rating, 245 reviews

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

LocationValueNearby

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.

5.0 out of 5 average rating, 116 reviews

Carriage House - Elora

LocationValueNearby

Guesthouse in Richmond Hill

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.

4.94 out of 5 average rating, 160 reviews

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

ValueFamilyAccess

Guesthouse in Little Portugal

A cozy living area features a dark sofa with patterned throw pillows, positioned next to a glass coffee table. Colorful artwork adorns the walls, adding character. A wooden ladder leads to the bedroom above, while large windows allow natural light to fill the space.

4.86 out of 5 average rating, 118 reviews

Cottage Vibe Private Guesthouse @ Queen West

ValueFamilyParking

4.75 out of 5 average rating, 52 reviews

A cozy bedroom features a queen-sized bed with a blue plaid comforter. A modern fireplace is set into a wood-paneled wall. Natural light enters through a window covered with light grey curtains. A soft area rug complements the space, while a small nightstand holds a clock.

Guesthouse in Erin

Retreat in Hiker's paradise with outdoor Firepit

ValueLocationComfort

A stylish studio room features a comfortable bed with a soft gray comforter, complemented by decorative lamps on either side. A modern artwork hangs above the bed, while a sleek dining table is positioned nearby. A TV is mounted on the wall, enhancing the space.

4.94 out of 5 average rating, 67 reviews

Cozy Guest Suite | Kitchenette & modern Bath

LocationFamilyHospitality

An inviting outdoor area features a stone patio, accompanied by a round table with four chairs and a vibrant orange umbrella providing shade. The red brick exterior of the home adds charm, with two large windows above offering natural light to the space.

4.98 out of 5 average rating, 43 reviews

Country Guesthouse~ Farm

LocationFamilyAccuracy

Guest house rentals with a washing machine and dryer

Guesthouse in Orangeville

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.

4.94 out of 5 average rating, 151 reviews

A bright & stylish urban studio

LocationValueLong stay

Guesthouse in Downtown Toronto

A spacious bedroom features a large queen-size bed with soft bedding and a bedside lamp on each side. A desk sits near the window, providing natural light, while a comfortable sofa is positioned against one wall. Elegant lighting enhances the room's design.

4.91 out of 5 average rating, 129 reviews

Downtown - 1 Bedroom Home Upper unit of house

LocationFamilyWalkability

4.89 out of 5 average rating, 123 reviews

A well-appointed kitchen features wooden cabinets and sleek stainless steel appliances, including a gas stove and dishwasher. Countertops are made of granite, with a window providing natural light. Minimalistic decor is complemented by subtle lighting, enhancing the functionality of the space.

Guesthouse in Brantford

Langford Guesthouse

FamilyLocationParking

4.87 out of 5 average rating, 104 reviews

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

LocationFamilyAmenities

A modern kitchen area features sleek cabinets and new appliances, including a refrigerator and stove. A small dining table is positioned against the wall, complemented by a decorative bicycle wall hanging. Warm lighting enhances the clean lines of the space.

4.83 out of 5 average rating, 24 reviews

Cozy 2-Bedroom Basement Apt with Private Entrance

FamilyLocationAccuracy

4.78 out of 5 average rating, 55 reviews

Your Cozy Milton Retreat!

ValueFamilyCleanliness

5.0 out of 5 average rating, 12 reviews

Spacious + Modern Guest House

LocationFamilyHospitality

A spacious living room features a comfortable grey couch and two black armchairs, each with decorative cushions. A glass coffee table sits on a patterned rug, while a modern TV displays various streaming options. Natural light enters through two windows, enhancing the airy feel.