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Guesthouse holiday rentals in Milton

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Top-rated Guesthouses in Milton

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

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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
4.94 out of 5 average rating, 195 reviews

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.

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
4.94 out of 5 average rating, 162 reviews

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, 1-2 free parking

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
4.98 out of 5 average rating, 438 reviews

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.

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
4.97 out of 5 average rating, 239 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS OCTOBER 19-30 NOVEMBER 1-30 DECEMBER 1-31 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. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging on-site. Views from the cottage include peaches, vineyards and orchards.

Guest favourite
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.
Guesthouse in Halton Hills
4.91 out of 5 average rating, 147 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, &the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay. You WILL hear wildlife and farm animals here.

Top Guest favourite
The bedroom features a spacious bed with soft, white bedding. A chandelier with multiple lights hangs from the ceiling. Two bedside lamps are placed on nightstands, and light-colored curtains frame a window, enhancing the overall ambiance.
Guesthouse in Lincoln
4.96 out of 5 average rating, 152 reviews

Private Guesthouse in Jordan

Centrally located among Niagara’s fruit farms and wineries is our private loft. Our loft is a large open concept space that offers a cozy haven, blending modern comfort with local charm. Relax with a morning coffee on the balcony that overlooks the harbour estates vineyard or enjoy a nightcap while watching the sun set. Perfect for solo travellers or couples seeking a serene escape. 5 min drive to Charles Daily Beach Down the road to Pearl Morisette Restaurant 20 min to Niagara Falls.

Top Guest favourite
A cozy studio space features high ceilings with exposed wooden beams and a bright, airy atmosphere. A double bed is adorned with a soft blanket, while a seating area with a rattan chair and small sofa invites relaxation. Natural light flows through large windows, illuminating the room.
Guesthouse in The Junction
4.91 out of 5 average rating, 574 reviews

Beautiful Studio Guelph ~ Secluded Urban Cottage

Experience an independent, private, sparkling clean studio close to downtown Guelph with full amenities. Located in a gorgeous tree-filled 200 ft backyard, this cozy urban cottage has a comfortable double bed with new mattress, gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, sleeping loft, and private back patio. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

Top Guest favourite
An open living space is presented, featuring a comfortable sofa and a stone fireplace. The area is illuminated by natural light from the garden view windows. In the background, a bedroom with a queen size bed is visible, along with a dining table and chairs.
Guesthouse in Mississauga
4.99 out of 5 average rating, 224 reviews

Zorro Guest Suite • Central, Cozy & Private

Newly built cozy attached guest suite w/ private entrance. On a cul-de-sac in a quiet area, yet centrally located. Acoustically insulated for a quiet nights sleep. * 15/20 minutes to YYZ Airport & 5 minutes to Square One shopping center. * 30 minute drive to Toronto * 1 hr drive to Niagara Falls. * Ideal for traveling couples or a solo professional. * Garden views from indoors and from a designated outdoor patio space. * 1 parking spot available in our driveway.

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
4.96 out of 5 average rating, 133 reviews

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

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
4.98 out of 5 average rating, 210 reviews

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.

Top Guest favourite
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
4.95 out of 5 average rating, 418 reviews

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.

Top Guest favourite
A spacious living area features a comfortable grey sectional sofa and two blue chairs. A wooden dining table with brown chairs occupies one side, while a fireplace with a wooden mantle serves as a focal point. Natural light enters through multiple windows.
Guesthouse in Brantford
4.99 out of 5 average rating, 197 reviews

The Pines, charming retreat close to the highway

*Registered Short-Term Rental Business* Licensed Granted by the City of Brantford Your family will be close to everything when you stay at this centrally located place, seconds from the highway! Located on 3 acres in the city of Brantford. Private driveway four-vehicle parking. Lots of walking space & outdoor seating to take in the sun or just want privacy.

Popular amenities for Milton guesthouses

Quick stats about guesthouse rentals in Milton

  • Total rentals

    20 properties

  • Nightly prices starting at

    $62 AUD before taxes and fees

  • Total number of reviews

    620 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore