Guesthouse vacation rentals in Milton

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Top-rated guesthouse rentals in Milton

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Top guest favorite
The calm water of Lake Ontario reflects shades of blue and orange as the sun sets on the horizon. The scene captures the serene transition of day to night, with gentle ripples enhancing the peaceful atmosphere of the lakeside location.
Guesthouse in Lincoln
4.96 out of 5 average rating, 126 reviews

Guesthouse on Lake Ontario Niagara

Please mark this listing as a favourite. Unwind at our cozy guest house. Enjoy the direct waterfront views from the living room, bedroom and private Muskoka chairs. We are located along the shore of Lake Ontario amongst the fruit belt of the Niagara region. vineyards, peach, nectarine and plum trees. Shops, Restaurants, and Award Winning Wineries. FREE TESLA charger 🔌 on-site. Free bottle of wine Direct Lakefront OPEN TIMESLOTS FEBRUARY 13 (today) 1 night/2 days APRIL 1-30, 2026 MAY 1-31, 202

Top guest favorite
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
4.95 out of 5 average rating, 141 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Top guest favorite
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, 210 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 favorite
A cozy living area features a leather sofa and an accent chair beside a coffee table. A fireplace is framed by a white brick wall, and a television is mounted above. Natural light streams through large windows, illuminating a dining table with metal chairs.
Guesthouse in Hamilton
4.77 out of 5 average rating, 200 reviews

Newly renovated, homely 2 bedroom suite

Welcome to our homey secondary suite with big windows and lots of natural light. Our freshly renovated suite of 900 sqft is ideal for a family or friends visiting Hamilton. The open concept is ideal for staying in or using it for evening purposes. Make your stay the most comfortable and fun with our eye-catching suite. Enjoy nearby restaurants, movie theater, golf clubs, parks, conservation areas. We can't wait to welcome you soon. Free street parking right in front of the house at all time

Top guest favorite
The living area features a light grey couch facing a wall-mounted television, with a stone fireplace below. A circular wooden coffee table sits on a patterned area rug, surrounded by black and green lounge chairs. Decorative shelves hold various items, enhancing the space's contemporary feel.
Guesthouse in Hamilton
5 out of 5 average rating, 102 reviews

Headwater Haven | 2 King-Beds

Experience luxury and tranquility just outside Dundas! Situated minutes from local golf courses, waterfalls, trails, biking routes and the Dundas Valley Conservation Area. This 2-bedroom sanctuary features King-sized beds, boasts 12-Ft ceilings and an indoor fireplace, offering elegance and comfort. Enjoy the spa-like bathroom with its heated floor, large tiled shower and dual rainfall showerheads. Unwind in the cozy living area or step outside to the patio and make memories by the campfire.

Top guest favorite
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
4.92 out of 5 average rating, 169 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 favorite
Guesthouse in Mississauga
4.99 out of 5 average rating, 255 reviews

Zorro Guest Suite • Private, Cozy & Central

Welcome to our modern, cozy guest suite with your own private entrance—ideal for traveling couples or solo professionals looking for a quiet, comfortable stay. We’re tucked away on a peaceful cul-de-sac, yet still close to everything. Acoustically treated to ensure absolute privacy and a restful night’s sleep. HIGHLIGHTS • 15/20 mins to YYZ & 5 mins to Square 1 shopping. • 30 mins to Toronto & 1 HR to Niagara Falls. • Garden views from inside & outdoors. • 1 driveway parking spot.

Top guest favorite
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, 594 reviews

Sweet Studio Cottage Cozy Fireplace Backyard Haven

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 sauna. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

Superhost
Guesthouse in Brampton
4.78 out of 5 average rating, 330 reviews

Newly renovated & contemporary 2 Bdrm Basement Apt

Welcome to our newly renovated spacious 2 bedroom, 1 bathroom basement apartment with a full kitchen. Unlimited and strong high-speed Wi-Fi. We have a flat screen TV with Google Chromecast so that you can view and stream from your smartphone/laptop. Close to LCBO (5 minute walk), NoFrills (5 minute walk) and Pearson Airport (15-20 mins drive). The property is located in the borderline between Brampton and Mississauga on the intersection of Steeles Avenue & Mavis Road.

Guest favorite
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
4.97 out of 5 average rating, 144 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 favorite
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, 433 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.

Guest favorite
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.
Guesthouse in Hamilton
4.83 out of 5 average rating, 169 reviews

Independent Suite Near Airport 4 Guests 2 Qn. Beds

Escape to our serene suite, perfect for 2-4 guests with two queen beds, a private ensuite bathroom, and a kitchenette (no stove). Unwind with a Smart TV for leisure. Excellently located between Niagara Falls, London, Waterloo and Toronto, close to Hamilton Airport, Limeridge Mall, and various attractions. Enjoy Hamilton's famous waterfalls, trails, gardens, and museums. Ideal for travelers seeking comfort and convenience.

Popular amenities for Milton guesthouse rentals

When is the best time to visit Milton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$14,425 GYDG$14,634 GYDG$12,962 GYDG$13,798 GYDG$14,843 GYDG$15,679 GYDG$17,561 GYDG$17,979 GYDG$16,934 GYDG$15,888 GYDG$16,098 GYDG$15,261 GYD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

Quick stats about guesthouse rentals in Milton

  • Total vacation rentals

    Explore 20 vacation rentals in Milton

  • Nightly prices starting at

    Milton vacation rentals start at G$10,453 GYD per night before taxes and fees

  • Verified guest reviews

    Over 650 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Milton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milton rentals

  • 4.8 Average rating

    Milton stays are highly rated by guests—averaging 4.8 out of 5!

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