Guesthouse vacation rentals in Caledon

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Top-rated guesthouse rentals in Caledon

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

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Guest favorite
The inviting living area features warm wood accents and a cozy seating arrangement. A brick fireplace stands as a focal point, complemented by large windows that flood the space with natural light. Ferns add a touch of greenery, enhancing the relaxing atmosphere.
Guesthouse in Uxbridge
4.93 out of 5 average rating, 169 reviews

Guesthouse w/Woodstove in Nature Near Trails & Spa

Relax and unwind at this peaceful and private Guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

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, 200 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 sleeping area features a spacious bed adorned with soft linens. A neutral color palette is complemented by light streaming from a nearby window. A modern TV and comfortable seating area are visible in the background, providing a relaxed space for entertainment.
Guesthouse in Angus
4.98 out of 5 average rating, 264 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to Centre Street Studio! Our 600 sq/ft bachelor suite offers a private, clean and cozy retreat. Enjoy access to a private 2 person hot tub and/or explore our local trail system. Beautiful Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. A 2-min drive to town amenities. NOTE: We don't host guests new to AirBNB or who have no previous reviews attached to their profile.

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, 441 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.

Top guest favorite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie
5 out of 5 average rating, 223 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

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, 156 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
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, 586 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
A cozy living area features a stone accent wall, paired with modern furnishings. Two armchairs and a small table provide seating options, while a large TV is mounted on the wall across from a comfortable sofa. Natural light filters in through the nearby window.
Guesthouse in Mississauga
4.99 out of 5 average rating, 234 reviews

Zorro Guest Suite • Private, Cozy & Central

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, 136 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, 423 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 favorite
A newly renovated guesthouse is showcased, featuring a wooden exterior and a spacious deck. Comfortable patio furniture, including a red chair and two black chairs, adorn the deck. Stone pathways lead to the entrance, surrounded by well-maintained greenery and trees.
Guesthouse in Niagara Falls
5 out of 5 average rating, 226 reviews

Hilltop Hideaway

A unique, newly renovated guesthouse nestled on 5 acres ,surrounded by trees with a private walking trail. Just 10 minutes from Niagara Falls and Niagara on the Lake!! 2 minutes to the Niagara Wine Route and many restaurants, wineries, and shopping. Modern farmhouse charm and decor throughout this open concept one bedroom guesthouse. A perfect retreat to relax, restore and explore Niagara.

Popular amenities for Caledon guesthouse rentals

When is the best time to visit Caledon?

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Avg. price€ 60€ 57€ 56€ 58€ 62€ 64€ 66€ 68€ 69€ 63€ 60€ 60
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Quick stats about guesthouse rentals in Caledon

  • Total vacation rentals

    Explore 30 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 1,370 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Caledon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals

  • 4.9 Average rating

    Caledon stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre

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