Guesthouse holiday rentals in Milton

4.97 out of 5 average rating, 346 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.

FamilyLocationHeating

4.84 out of 5 average rating, 226 reviews

Hamilton Beach Guesthouse with guest Kayaks

LAKEFRONT* 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 overlooking the lake. Right on the waterfront trail, roller blade, bike, or enjoy the sandy beach. Very central for a Niagara winery and Toronto trip. Includes: Smart TV, 1 Parking spot, good Wi-Fi, Fire-pit , BBQ, Kayaks, Coffee& base cooking supplies. Certified of compliance the building code act, 1992, section 15.1

ValueLocationIndoor spaces

4.98 out of 5 average rating, 475 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

Private detached cottage 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. Approximately a 30 minute drive to NOTL wineries and Niagara Falls.

ValueLocationBathroom

4.96 out of 5 average rating, 335 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 OCTOBER 5-8 (3 nights/4 days) discounted book 1 night or all 3 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

ValueFamilyView

Guesthouse in Elora-Salem

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.

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.

LocationValueWalkability

4.99 out of 5 average rating, 146 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”

LocationFamilyPool

4.89 out of 5 average rating, 118 reviews

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, 213 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.

FamilyValueAmenities

4.95 out of 5 average rating, 131 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!

FamilyLocationQuiet

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.

5.0 out of 5 average rating, 128 reviews

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

LocationFamilyBathroom

4.96 out of 5 average rating, 231 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.

LocationValueBiking

4.98 out of 5 average rating, 234 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.

ValueFamilyBarbecue

4.94 out of 5 average rating, 466 reviews

The cottage sits nestled among vibrant foliage, framed by lush trees and blooming flowers. A flagstone pathway leads to the entrance, inviting guests to explore the colorful exterior, which features a charming yellow facade complemented by blue accents.

Guesthouse in Guelph

Private, sunny cottage steps from downtown Guelph

Our private cottage is steps from downtown Guelph. The cottage is complete with a kitchenette and a bathroom with a large shower. The cottage is a separate building located in our back garden.You access the cottage along the driveway and stone pathway through the back garden. There is free wireless Internet along with Rogers Ignite TV and Netflix. The living room is spacious and there is one bedroom with a king- sized bed.

LocationValueAccess

Popular amenities for Milton guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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.

Entire 1 Bedroom Detached Coach House

ValueFamilyWalkability

4.94 out of 5 average rating, 115 reviews

4.98 out of 5 average rating, 253 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

FamilyLocationView

Guesthouse in Richmond Hill

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.

Balcony House with Separate Entrance，free Parking

LocationValueParking

4.93 out of 5 average rating, 197 reviews

A modern living area features a large blue sectional sofa facing a glass coffee table. A vibrant urban wall art piece is displayed prominently above. Soft lighting illuminates the space, highlighting the warm tones of the wooden floor and greenery in the corner.

4.79 out of 5 average rating, 147 reviews

Entire Guest Suite in Brampton

LocationValueOutdoor spaces

Guesthouse in St. Catharines

Lakeshore Loft-quiet and comfortable 1 bedroom apt

ValueFamilyIndoor spaces

4.95 out of 5 average rating, 165 reviews

4.81 out of 5 average rating, 64 reviews

Guesthouse in Milton

Your Cozy Milton Retreat!

ValueLocationAccuracy

4.96 out of 5 average rating, 48 reviews

A charming entrance features a welcoming sign and a wooden bench beside flower pots. A gated area leads to a patio with an umbrella and a stone table, surrounded by greenery and trees, creating a serene outdoor space.

Guesthouse in Milton

Eramosa Airbnb in Rockwood, ON

LocationValueBathroom

Superhost

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.

Guesthouse in Milton

Milton Stay Near 401 | Toronto Airport 25 Minutes

FamilyLocationIndoor spaces

4.73 out of 5 average rating, 37 reviews

Guesthouses with a patio

Guesthouse in Elora-Salem

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.

Carriage House - Elora

FamilyLocationCheckout

5.0 out of 5 average rating, 122 reviews

4.95 out of 5 average rating, 251 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

FamilyLocationCleanliness

Guesthouse in Elora-Salem

Tiny Home retreat in quiet neighbourhood

LocationValueParks

4.97 out of 5 average rating, 121 reviews

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.

Detached Coach House | 1 Bdrm 1 Bath| Private HVAC

FamilyLocationCondition

4.94 out of 5 average rating, 163 reviews

4.77 out of 5 average rating, 56 reviews

Guesthouse in Erin

Retreat in Hiker's paradise with outdoor Firepit

LocationValueSleep quality

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.

4.94 out of 5 average rating, 47 reviews

Country Guesthouse~ Farm

LocationFamilyComfort

5.0 out of 5 average rating, 35 reviews

Guesthouse in Guelph

Private Pool House near UoG

LocationQuietPool

4.97 out of 5 average rating, 37 reviews

Cozy Private Garden Suite in Hamilton Mountain

LocationKitchenAmenities

Guest house rentals with a washing machine and dryer

4.9 out of 5 average rating, 131 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

FamilyValueAccuracy

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.

A bright & stylish urban studio

ValueLocationAir conditioning

4.94 out of 5 average rating, 152 reviews

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.

Downtown - 1 Bedroom Home Upper unit of house

ValueLocationAmenities

4.91 out of 5 average rating, 134 reviews

A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. A rustic barn door opens to the bedroom. The dining space includes a dark wood table surrounded by four chairs, complemented by a cozy sofa adorned with colorful cushions.

5.0 out of 5 average rating, 61 reviews

Private & Detached Downtown Brampton Garden Suite

ValueLocationNearby

4.95 out of 5 average rating, 19 reviews

Fireside 3BR by Canterra Stays · Sleeps 6

FamilyLocationKitchen

4.94 out of 5 average rating, 34 reviews

A well-lit bedroom features a spacious bed with crisp white linens and neatly arranged towels. Two nightstands with lamps are positioned on either side, while a stylish framed piece of art decorates the wall. A mirrored closet adds a touch of spaciousness to the room.

Guesthouse in Caledon

Cozy Private Basement Bedroom with ensuite

LocationValueDecor

4.89 out of 5 average rating, 35 reviews

A bright living area features a comfortable sofa and a wooden coffee table, complemented by decorative pillows. Natural light enters through sliding glass doors that lead to a private outdoor space. An adjacent staircase with a glass railing adds a modern touch to the setting.

Guesthouse in Islington

NEWLY Built Garden Suite | Private + Parking

FamilyValueCheck-in