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, 165 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.

Superhost
A modern kitchen features stainless steel appliances, including an oven and refrigerator. White cabinets provide ample storage, while a sleek countertop offers space for food preparation. A clear dining chair reflects the contemporary design, and a small vase with yellow flowers adds a touch of color.
Guesthouse in Brampton
4.86 out of 5 average rating, 173 reviews

Newly Renovated 2 bdr basement

Newly renovated cozy 2 bdr basement apartment with a seperate entrance Very clean & peaceful space perfect for & short term stay Friendly neighborhood - parks, trails & amenities >Major intersection: Sandalwood & Hurontario * 10 mins to highway 410 * 2 mins walk to bus stop * 5 mins walk to amenities * 10 mins > downtown Brampton & train station * Free parking, self check in *Like hotel stay experience *High quality white beddings ● Verified ID ●No parties, pets, smoking, illegal activities

Top guest favorite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville
4.95 out of 5 average rating, 375 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

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 :)

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.

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, 150 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.

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
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, 420 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 cozy living room features a mix of dark and light furnishings, including a large sofa and an accent seating area. Natural light streams through multiple windows, illuminating the space. A TV is mounted above a decorative fireplace, accompanied by a coffee table made from reclaimed wood.
Guesthouse in Elora
4.96 out of 5 average rating, 443 reviews

Wrights Coach House -Visit the Village of Lights!

The Wright's Coach House offers a quiet and rustic retreat that is only steps to the beautiful downtown village of Elora! This private space offers a cozy yet spacious area with room for 6 guests. From the surrounding woods to the scenic walk downtown we can offer a quiet stay & give you the secrets of the locals to give that extra boost to your visit. Come and see us!

Popular amenities for Caledon guesthouse rentals

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$14,434 GYDG$13,807 GYDG$13,388 GYDG$14,016 GYDG$14,853 GYDG$15,480 GYDG$17,363 GYDG$17,782 GYDG$17,154 GYDG$15,271 GYDG$14,434 GYDG$14,434 GYD
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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 G$6,276 GYD 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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