House holiday rentals in Dufferin County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Dufferin County

House rentals with a pool

Superhost
Home in Lisle
4.73 out of 5 average rating, 30 reviews

Hidden Oasis: Pool, Hot Tubs, & Starry Fire Pits

TeresaRating, 5 stars4 months ago
We had a fantastic experience staying at this beautiful home! From the start, the host was incredibly responsive and made sure all my questions were answered promptly. They were super friendly and welcoming. The house itself was amazing – spotless, spacious, and beautiful location. You could tell the host really cares about the space, and it had everything we needed for a comfortable and relaxing stay. We will definitely be booking here again next time we are in town. Highly recommend this place to anyone looking for a great stay!
Guest favourite
Home in Mono
4.98 out of 5 average rating, 41 reviews

Country Family Getaway with Pool and Trails

JoshRating, 5 stars2 days ago
To say we lucked out finding this home and its owners is a massive understatement. From the moment we booked to the day we departed—and even after—Mike and Kim went above and beyond to make our multi-generational family stay and 50th anniversary celebration a complete success. We’re so grateful to have found them. Initially, we were just planning to enjoy their beautiful, well-appointed stone farmhouse, set on immaculate grounds with a stunning saltwater pool. Then we learned we could rent a separate event space for the celebration—a gorgeous greenhouse at the top of the vineyard. To top it off, Kim and her family offered to cater the event. Everything was flawless. The guests were overjoyed with the food, the setting, and the whole experience. Most importantly, our parents had the most epic anniversary we could have imagined. Thank you for making it all possible. We’ll be back any chance we get—and we’ll be recommending you to everyone we know! !
Superhost
Home in Orangeville
4.69 out of 5 average rating, 16 reviews

Private cottage heated pool/HotTub/Games 20 Acre

DrewRating, 5 stars3 weeks ago
A great spot for a short escape from the city! Amazing property! Very private. Owner and maintence team were procative and prompt. Would have liked to see a book with general instructions on the property. We had to discover where the outdoor couch cushions were stored for example, I also feel the pool being 'not ready' was a bit of a bait and switch with the rental. It was not clear on how the property managers would like us to handle garbage and there was no ideal place to put the bags. We ended up putting them in the mudroom area (as oudoors would only be a larger mistake given local wildlife) Linnens were clean, Kitchen and the whole property is very nice and well mantained. A great spot for a short escape from the city. Would rent again! Thank you for a wonderful stay.
Superhost
Home in Mono
4.78 out of 5 average rating, 18 reviews

Custom home that feels like the Spa

ChrisRating, 5 stars2 weeks ago
Kris was awesome to work with, super accommodating, even better place 5/5 stars for us on this spot! Definitely recommend!
Home in Mulmur
5 out of 5 average rating, 14 reviews

Private Pool/Pond/River in Secluded 14Acres Estate

AlyssaRating, 5 stars22 months ago
Redwood Estate was a beautiful location to host my family’s 2023 cottage weekend. The place was just as described. I’m pretty picky when it comes to accommodations, but Razia’s place was super clean and definitely met my standards! There were ten guests with us - four families - and the house was big enough for us to all spend time together and also have our own privacy. The house is well stocked - we brought a lot of stuff that we probably didn’t need to. The grounds are absolutely beautiful. Lots to see and do for all ages. The pool was of course a big hit with everyone. We just so happened to time our stay with a meteor shower and we’re able to spend the night stargazing!
Guest favourite
Home in Shelburne
4.83 out of 5 average rating, 29 reviews

Primrose Park

PeterRating, 5 stars12 months ago
Rose was a wonderful host and the accommodations exceeded our expectations. Had a lovey stay and would book again.
Top guest favourite
Home in Alton
4.97 out of 5 average rating, 94 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

RachelRating, 5 stars1 month ago
An absolutely stunning property with great amenities - the hot tub soak was super appreciated. Instructions to get to the property and check-in are super clear, and everything is clearly labelled in the house. Paige supplies everything you need at the house to cook, clean up, and keep everything running. She is super responsive and very helpful! Thank you for a lovely stay and we are already hoping to come back!
Guest favourite
Home in Mono
4.89 out of 5 average rating, 38 reviews

Mono Springs - Dream Country Escape w pool/hot tub

VikramRating, 5 stars5 months ago
“A Slice of Heaven on Earth” We had the most incredible stay at this breathtaking property! Nestled on 10 sprawling acres, this magnificent estate exceeded our wildest dreams. The moment we stepped foot on the grounds, we knew we were in for a treat. The property itself is stunning, with beautifully manicured lawns, serene walking trails, and picturesque views that seem to stretch on forever. We spent hours exploring the grounds, discovering hidden gems and soaking up the tranquility. The location is equally impressive, offering the perfect blend of seclusion and accessibility. We felt like we were a world away from the hustle and bustle, yet still within easy reach of local amenities. Our hosts were warm, welcoming, and incredibly attentive, ensuring our stay was nothing short of perfection. If you're looking for a truly unforgettable experience, look no further! This incredible property has left us with memories we'll cherish forever.

Weekly house rentals

Home in Orangeville
4.63 out of 5 average rating, 27 reviews

Charming Historical Home in Hockley Village

TaylorRating, 5 stars36 months ago
Cathy’s home is a historic century home, located across the street from a quaint general store that really has a bit of everything! The home is spacious and well equipped, and it offered us the perfect space as we were in town for a wedding. Thanks, Cathy!
Home in Everett
4.6 out of 5 average rating, 121 reviews

Paradise Suites - Peaceful Getaway - 5+ Acres

NeenuRating, 5 stars2 months ago
*5/5 "Perfect spot for our crew! This private place was super spacious, making it ideal for large gatherings. The extras like additional beds and comforters were a huge plus. We also paid a bit extra for the basement, which was totally worth it - great added space! Big shoutout to the host for being super flexible with check-in and check-out times. Really appreciated the understanding and accommodation. Only minor note is keeping an eye on waste disposal, but conveniently located nearby and open except holidays. All in all, highly recommend for anyone looking for a comfortable and adaptable space! Will definitely book here again for our next event.
Home in Orangeville
4.47 out of 5 average rating, 15 reviews

Charming | Ping-Pong | Treadmill | BBQ | Patio

DarrinRating, 5 stars1 month ago
We flew into Canada for our son's wedding. When we booked we didn't realize that it was 10 minutes away from the venue. Based on our last air bnb experience this was super fantastic. The host was super and timely in his response to our questions. The property was excellent and well kept. I would definitely recommend it to any and everyone and would definitely stay at this location in the future.
Home in Southgate

The Perfect Family Retreat (Brand New Entire Home)

LoganRating, 5 stars3 months ago
This was the perfect getaway for a night. Felt like a great reset with nice clean bathroom and showers. Kitchen was spotless and easy to use.
Home in Orangeville
New place to stay

Modern Family Comfort

RoxaneRating, 5 stars2 weeks ago
We loved our stay! Quiet neighborhood and close to everything we needed!
Home in Mansfield
4.55 out of 5 average rating, 20 reviews

Peace and Quiet at our Vacation home

KylieRating, 5 stars34 months ago
Pleasantly surprised by the cleanliness and size of the chalet. Much nicer than the photos depicted. Perfect location for a lot of day trips since the location is very central.
Home in Lisle
4.78 out of 5 average rating, 9 reviews

Serene country retreat - your home away from home!

MichelleRating, 5 stars36 months ago
We booked this home for 1 night as a group because we were attending a wedding in the area. The home was large with plenty of sleeping space and bathrooms which was great. The bedding and pillows were extremely comfortable. Overall we had a great stay. Ameet also was very responsive after our stay when one of our group realized they had forgotten some items and worked with them to find a way to get the items shipped back to them. Thank you Ameet!
Home in Shelburne

Dufferin Retreat

RocchinaRating, 5 stars1 month ago
Felicia and her family were amazing. Would love to stay here longer, but this is an amazing place. They were very, very responsive very very there for you when you needed them and very clean. Thank you Felicia for everything.

Private house rentals

Home in Shelburne
New place to stay

Farmhouse that can accommodate up to 10 people

ChrisRating, 5 stars1 month ago
This was the nicest Airbnb I have stayed at by far. The host communicated above and beyond any other host I have dealt with. The house and the property are gorgeous and very well maintained. We will be returning next time we're in the area.
Home in Shelburne
4.29 out of 5 average rating, 7 reviews

Cozy Home Close to Blue Mountain and Collingwood

NakitaRating, 5 stars3 months ago
Melissa is a lovely Host - very responsive, easy to work with, exceptionally professional and pleasant. Will absolutely book with Melissa again!
Home in East Garafraxa

Spacious Country Retreat

MichaelRating, 5 stars2 weeks ago
Just stayed for a week and Ranjit and his family were perfect hosts, very communicative and responsive to any questions or messages. We had a small issue with the firmness of the mattresses (they were only too firm as they were brand new) and once this was brought to Ranjit’s attention all 3 mattresses were replaced the say day! Exceptional service, you can’t ask for anymore! We will definitely stay again if we are in the area! Thanks!
Home in Alton

Waterfront Luxury Home

MeganRating, 5 stars1 week ago
We loved the is place! We were in town for a wedding at the Mill and it was a quick walk to it. There was a restaurant across the road that we got takeout from which was great but you could also sit in a listen to a band. We had breakfast at the cafe down the street which was only a short walk. The cafe was so good! The house was absolutely beautiful! There were 7 of us and there was so much room. Each group had their own room and bathrooms. The kitchen was beautiful and the outdoors area was stunning! Aaron and family had lots of amenities and activities for us to do. It honestly was one of the best places we’ve stayed. We’d highly recommend and if we ever make our way to Alton again would love to stay again!
Home in Shelburne

Enchanted Medallion 20 guests-send request 6 more.

DeborahRating, 5 stars3 weeks ago
We had a perfect stay in this large beautiful home, lots of comfortable spaces for everyone. Clean and modern. Very well-equipped kitchen.
Home in Rosemont

Beautiful Villa in Rosemont

DakshRating, 5 stars2 months ago
It’s a nice place, we had a great time
Home in Caledon Village
New place to stay

Charming Caledon Village Home

JackRating, 5 stars2 weeks ago
Nanci’s place was perfect for me and my friends. To come back and relax after busy days, the house was ideal. Also my friendly and responsive to any questions that’s asked. Happily stay there again
Home in Belfountain
New place to stay

Cozy Cabin Vibes | 2-Bed + Full Kitchen + Office

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