Mansion holiday rentals in Oshawa

Find and book unique mansions on Airbnb

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Popular amenities for Oshawa mansion rentals

Luxury mansion rentals

Home in Pickering
4.66 out of 5 average rating, 41 reviews

Superhouse with space for all! Kids+Grands+more

MarkRating, 5 stars6 days ago
Karla was one of the best hosts I have ever experienced renting from. The house looked exactly like the pictures and the place was huge enough to provide a comfortable living space for me and my nine other friends over the weekend. The neighborhood is extremely quiet and safe for anyone who is worried and only about a 30 minute drive away from the city of Toronto. If I ever have to come back to Toronto with a big group, Karla will be the first person I will contact.
Home in Goodwood
4.54 out of 5 average rating, 13 reviews

Cozy 10acre Farm Cottage in Goodwood: Hermoso Stay

EdRating, 5 stars2 weeks ago
Perfect place to have a diaper party for our friend. Very big place with tonnes of space and bedrooms for a large group. It was fairly clean for our arrival. The fridge smelled and should've been disinfected. But the fact Sivabooshan was good to be able to host our large group and the house had all of the basic amenities needed, it was the perfect arrangement. Thanks again!
Guest favourite
Cottage in Goodwood
4.82 out of 5 average rating, 72 reviews

Family fun! Hot tub/snooker table/Movie Room!

BenjaminRating, 5 stars1 month ago
I stayed at this air b&b with 14 people. We thoroughly enjoyed our time and the host was great & very responsive! Highly recommend if you are looking for some time away or need a home base for a large group just outside of Toronto
Superhost
Home in Pickering
4.75 out of 5 average rating, 32 reviews

Stunning Farmhouse In Pickering!

ShishirRating, 5 stars1 month ago
The property is Amazing, we really enjoyed the place. It’s completely private, so we had a good time disconnecting from the city life. The house being old was kept very clean and well maintained. Loved the time spent
Guest favourite
Home in Whitby
5 out of 5 average rating, 6 reviews

Modern & spacious airy home backing on ravine

ShujatRating, 5 stars8 months ago
Enn is fantastic host and took care of us during a long stay at her place. She keeps it immaculate and tastefully decorated. Questions were answered quickly. Our needs were met 110% and would recommend her for families looking for long term stays.
Guest favourite
Home in Scarborough
4.91 out of 5 average rating, 35 reviews

Spacious RougeView Home|2 Kitchens & 8-car Parking

SteveRating, 5 stars6 days ago
The house was just as described! We had an amazing hockey tournament weekend with six dads and seven kids. There were plenty of beds and bedrooms, and the huge backyard was perfect for the kids to hang out and play football. Check-in and check-out were effortless, and the kitchen had everything we needed. We’d definitely stay here again!
Villa in Windfields
4.8 out of 5 average rating, 50 reviews

3300ft ² Luxury Villa | 3 Levels | 3 TVs | Hot Tub

AdamRating, 5 stars2 weeks ago
Great stay - all 3 hosts were very communicative, any issues were dealt with immediately, great flexibility. House looked great and had a great time. Would book again.
Home in Oshawa
3.71 out of 5 average rating, 7 reviews

Beachfront Retreat: Cozy 7B/2.5B with Studio Unit

RajRating, 5 stars6 months ago
This space was bright and clean with a stunning view. It was peaceful and quiet with a fully equipped kitchen for preparing meals. The host was very responsive and took care of our needs. Highly recommend…

Pet-friendly mansion rentals

Guest favourite
Home in Oshawa
4.97 out of 5 average rating, 29 reviews

Cheerful 4 bedroom over 3350 sq ft living area

SydneyRating, 5 stars8 months ago
Spent a wonderful weekend at this home while visiting family nearby! The house is very spacious and the kitchen was stocked with all the dishes and cookware we needed to make our own meals. The en-suite bathrooms for each bedroom was a great bonus. We were all very impressed, and would happily stay here again next time!
Guest favourite
Home in Pickering
5 out of 5 average rating, 16 reviews

Just Like Home- Brand New 4 Bedroom Home

LhannieRating, 5 stars3 days ago
Jason is responsive and easy to communicate. We are happy with our stay. The house is great very comfortable and clean. His place is very peaceful. I like the community. Thank you Jason, I highly recommend your house.
Guest favourite
Home in Windfields
5 out of 5 average rating, 9 reviews

EastCity 4BedRoom DetachedHouse

PhilipRating, 5 stars3 months ago
We booked Kathi's place for a volleyball tournament at Durham College/TUO and it was PERFECT. About 1.5km from the gym, lots of everything we needed close by. The house was immaculate. It is very new and everything worked perfectly. The small appliances present were exactly what we needed. The space was well laid out so couples could socialize or have their own space. The number of bathrooms was a massive bonus. Zero issues ever as each couple basically had their own. Kathi's communication is the Platinium Standard for AirBnB. She literally had answers to us within 10 minutes every time, which wasn't often but it was a major help to know she was right there. I would highly recommend her place if you are in the Durham area. It is large, clean, well fitted/laid out, and fresh. She has also priced it fairly and I think in the area she is excellent value for what you receive.
Superhost
Home in Pickering
4.7 out of 5 average rating, 10 reviews

Seasons Vacation: Cozy 4B/2.5B,Kitchen,Parking,5G!

JaishreeRating, 5 stars2 weeks ago
We stayed at this property to attend a family reunion. Even though the reunion was at a different city, we would be meeting family and friends after a long time. This property was ideal for us since we were able to invite a couple of families for tea and were able to catch up. The bright sunshine coming in through the windows, was my favorite. The kitchen and living room with a door to the small patio was ideal. We did not do much cooking except making coffee and tea, for which this kitchen is well equipped. The bedrooms upstairs with 2 full baths were comfortable and bright. The laundry was a big advantage. But bring your own detergent. Pickering is a city adjacent to Ajax. Both these cities are rich in ethnic diversity. A big plus!
Guest favourite
Home in Ajax
4.94 out of 5 average rating, 83 reviews

Entire Home - Spacious 4 Bedroom Near Deer Creek

MigdaliaRating, 5 stars5 months ago
This is our second stay at Sandra’s and we had a wonderful time! She is a very responsive and easy going host, and was very helpful throughout our stay. Her place is beautiful and perfect for large families with pets!
Guest favourite
Townhouse in Pickering
4.93 out of 5 average rating, 44 reviews

Cyberspace - no cleaning fees, New Private Hot Tub

MikeRating, 5 stars6 days ago
Alan’s place was perfect for our getaway! The home is huge with tons of space for everyone to spread out and relax. We loved the hot tub and spent hours around the pool table. Great setup, clean, and well-equipped — would definitely stay again!
Superhost
Home in Ajax
4.78 out of 5 average rating, 49 reviews

HiddenGem: home away from home

Sarah-GraceRating, 5 stars3 weeks ago
Pushp was a great host! He was very responsive to any questions that I had.
Superhost
Home in Haydon
4.86 out of 5 average rating, 14 reviews

The Bliss

GemmaRating, 5 stars2 weeks ago
We enjoyed our stay at The Bliss, everything was as described. The host was very friendly and communicated well, and was very flexible with us regarding check in. The house was beautiful, clean and extremely comfortable. We would definitely stay again! Thank you!

Mansion rentals with a pool

Guest favourite
Home in Ajax
4.94 out of 5 average rating, 47 reviews

Beautiful Cottage in Ajax

Ann-MarieRating, 5 stars1 week ago
This is our second time staying at Sabesan’s beautiful home. The house is gorgeous, lots of space for activities, beds are so comfy and the outdoor space is amazing. Sabesan is a perfect host; very responsive, and genuinely wants your stay to be the best one. We will be back next year!
Guest favourite
Home in Port Perry
5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

AndreaRating, 5 stars8 months ago
While journeying from the UK to Port Perry, we were fortunate to stay at the Horse Farm Luxury Estate for a week in September. Situated next to a riding school, the tranquil area was perfect for relaxation. Horses grazed in the paddock beside the house – their beauty admired from a distance as per the rule 'do not touch the horses'. The house's position was ideal for exploring the surrounding area, including Port Perry, with easy access to nearby highways for visits to Oshawa, Toronto, and even Niagara Falls. The spacious house had numerous amenities, such as a basement games room and a ground floor club area with a bar. A conservatory connected to a deck and hot tub. Anthony's great communication and assistance made our stay stress-free after a long journey. I highly recommend Horse Farm Luxury Estate for a comfortable stay in Port Perry.
Top Guest favourite
Home in Scarborough
4.98 out of 5 average rating, 47 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars3 days ago
We had a delightful stay at Jasmine’s place. The space was impeccably clean and thoughtfully decorated, making it feel like a true home away from home. Jasmine was an exceptional host—attentive, communicative, and always ready with helpful replies with my questions. I highly recommend her place to anyone visiting the area and would love to return in the future.
Superhost
Home in Oshawa
4.8 out of 5 average rating, 30 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

NicoletteRating, 5 stars3 weeks ago
Neil's home is lovely, it's huge, and super clean. Neil was polite and responsive and made sure I had everything I needed. even when I forgot things he made sure they got returned! Definitely would book again!
Home in Ajax
4.85 out of 5 average rating, 13 reviews

Entire Modern Home | Spacious | Near Lake & Park

JustinaRating, 5 stars1 month ago
we really appreciated the home being clean and clutter free. The amenities allowed use to travel light and enjoy our stay. only thing I would recommend is a spaghetti strainer. Our stay was like Home away from Home. Thank you for your hospitality. Hope to come back soon.
Cottage in Pickering
4.53 out of 5 average rating, 58 reviews

Private Cottage Getaway in Nature

DianaRating, 5 stars2 weeks ago
What a wonderful space! Top-notch girls weekend getaway with a ton of space, a beautiful grassy yard with an outdoor pool. Peaceful and private location. Also, the cottage is enormous with a ton of bedrooms and everything you need for a comfy stay. Rachel is a flexible, friendly and responsive host. I'd recommend this property and Rachel to anyone! A space to host a big group is a rare find. Thanks, Rachel!
Superhost
Home in Pickering
4.84 out of 5 average rating, 50 reviews

Toronto Vacation Pool/Park/Zoo/Casino

ElizabethRating, 5 stars2 weeks ago
House was well situated for our purposes and rooms were spacious and clean. Nice to be able to turn on fireplace in one of the sitting rooms. Enjoyed our stay.
Guest favourite
Home in Scarborough
5 out of 5 average rating, 27 reviews

Family vacation home with Heated Pool-Toronto

CarolineRating, 5 stars10 months ago
Wasim and Hasan are wonderful hosts. Their home is comfortable and spacious and all our guests enjoyed their stay. The pool was a hit. We would not hesitate to return again.

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