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Guesthouse vacation rentals in Milton

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Top-rated guesthouse rentals in Milton

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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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
4.96 out of 5 average rating, 139 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, 196 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.

Top guest favorite
A cozy studio space features a large bed with soft textiles, complemented by a compact kitchenette with a small fridge and microwave. Light wooden cabinetry provides storage above, while a set of stairs leads to the elevated sleeping area.
Guesthouse in Elora
4.96 out of 5 average rating, 100 reviews

Studio Blue, tiny home retreat

Keep it simple at this peaceful and centrally located place. Walking distance to: ~Elora's shops ~ sites/ attractions ~festivals ~trails The stocked kitchenette includes: ~Small fridge ~Sink ~Microwave ~Hotplate ~Kettle ~French press for coffee ~toaster ~small blender ~All dishes and cutlery ~EVOO, Vinegar, Salt, pepper, sugar, assorted tea, Regular and decaf coffee Also: ~New Double Bed Mattress (Mar 2025) ~Private patio & seating area ~Free Parking ~Wifi ~Access to the shared cooling pool

Top guest favorite
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 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
4.91 out of 5 average rating, 149 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
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, 155 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 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, 578 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.

Top guest favorite
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, 226 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 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
4.96 out of 5 average rating, 134 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
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
4.99 out of 5 average rating, 136 reviews

The Blue Lagoon | Pool & Coastal Tinyhome

Welcome to The Blue Lagoon! 2 minute drive from the mill & downtown. Offers guests a quiet, spacious & private guesthouse completely separate from the main dwelling. *The guesthouse & everything in side is brand new as of March 2024!* **Only Rules: No smoking inside & no pets** Guests have access to the ammenities in the backyard including a large pool, fire pit area & shaded patio complete with a BBQ. Come check out Elora's hidden gem!

Top guest favorite
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, 211 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 favorite
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, 198 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 guesthouse rentals

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 ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 620 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

  • 4.7 Average rating

    Milton stays receive an average rating of 4.7 out of 5 from guests

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