Guesthouse vacation rentals in Caledon
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Caledon
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Saint Catharines
4.98 out of 5 average rating, 381 reviewsPrivate Estate Coachhouse + Hot Tub near NOTL!
Guesthouse in Campden
4.98 out of 5 average rating, 376 reviewsDetached 450 sf cottage
Guesthouse in West Montrose
4.89 out of 5 average rating, 237 reviewsGrand River Pathways
Guesthouse in Collingwood
4.9 out of 5 average rating, 163 reviewsPrivate garage apartment near downtown Collingwood
Guesthouse in Little Portugal
4.87 out of 5 average rating, 444 reviewsUnique Studio with Sauna
Guesthouse in Mansfield
4.99 out of 5 average rating, 95 reviewsBrookside Cottage - Charming Rural Getaway Mulmur
Guesthouse in Woodstock
4.96 out of 5 average rating, 24 reviewsModern Country Escape
Guesthouse in Kimberley
5 out of 5 average rating, 9 reviewsCabin at Dragonfly Ridge in Beaver Valley
Guest house rentals with a patio
Guesthouse in Lincoln
4.98 out of 5 average rating, 113 reviewsCottage On Lake Ontario Niagara
Guesthouse in Bolton
5 out of 5 average rating, 7 reviewsAdorable 1-bedroom guesthouse with gas fireplace.
Guesthouse in Caledon
4.85 out of 5 average rating, 34 reviewsCaledon rural apartment with hot tub and pool
Guesthouse in Orangeville
5 out of 5 average rating, 31 reviewsIsland Lake Guest House
Guesthouse in Erin
4.79 out of 5 average rating, 24 reviewsGuest Suite (Basement) in Erin- Hiker's paradise.
Guesthouse in Erin
4.99 out of 5 average rating, 96 reviewsThe Captain's Cottage at Willow Pond
Guesthouse in Niagara Falls
5 out of 5 average rating, 60 reviewsBosco Hilltop Hideaway
Guesthouse in Hamilton
5 out of 5 average rating, 36 reviewsCharming Coach House steps away from Locke St.
Guest house rentals with a washer and dryer
Guesthouse in Newmarket
4.94 out of 5 average rating, 127 reviewsStylish 1-Bedroom Home in the heart of Newmarket
Guesthouse in Newmarket
4.85 out of 5 average rating, 202 reviewsPrivate cozy stylish fun Spacious Chill Basement
Guesthouse in Feversham
4.92 out of 5 average rating, 167 reviewsGuesthouse Getaway
Guesthouse in Niagara Falls
4.85 out of 5 average rating, 274 reviewsModern Niagara studio
Guesthouse in Niagara Falls
4.88 out of 5 average rating, 142 reviewsbright charming 2bdrm private suite walk to Falls
Guesthouse in Brampton
4.82 out of 5 average rating, 148 reviewsCozyStay in Brampton
Guesthouse in Richmond Hill
5 out of 5 average rating, 15 reviewsNew Cozy Entire 1 Bedroom Detached Coach House
Guesthouse in Guelph
4.98 out of 5 average rating, 65 reviewsThe Coach House by the Park
Quick stats about guesthouse rentals in Caledon
Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
640 reviews
Nightly prices starting at
$20 before taxes and fees
Destinations to explore
- Niagara Falls Vacation rentals
- Brampton Vacation rentals
- Niagara-on-the-Lake Vacation rentals
- Muskoka Lakes Vacation rentals
- Niagara Falls Vacation rentals
- Kitchener Vacation rentals
- Waterloo Vacation rentals
- Buffalo Vacation rentals
- Oakville Vacation rentals
- Barrie Vacation rentals
- London Vacation rentals
- Mississauga Vacation rentals
- House rentals Toronto
- Guesthouse rentals Toronto
- House rentals Canada
- Guesthouse rentals Canada
- Guesthouse rentals Ontario
- House rentals Ontario
- Guesthouse rentals Downtown Toronto
- House rentals Downtown Toronto
- Guesthouse rentals Mississauga
- House rentals Mississauga
- Rentals with pools Caledon
- Kid-friendly rentals Caledon
- Rentals with an EV charger Caledon
- Fitness-friendly rentals Caledon
- Waterfront rentals Caledon
- Rentals with a fire pit Caledon
- Rentals with outdoor seating Caledon
- Rentals with a fireplace Caledon
- House rentals Caledon
- Pet-friendly rentals Caledon
- Private suite rentals Caledon
- Rentals with a hot tub Caledon
- Rentals with lake access Caledon
- Condo rentals Caledon
- Townhouse rentals Caledon
- Family-friendly rentals Caledon
- Smoking-friendly rentals Caledon
- Monthly Rentals Caledon
- Rentals with breakfast Caledon
- Rentals with a patio Caledon
- Apartment rentals Caledon
- Bed and breakfasts Caledon
- Rentals with a washer and dryer Caledon
- Guesthouse rentals Regional Municipality of Peel
- House rentals Regional Municipality of Peel
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes