Vacation rentals in Oshawa

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Top-rated vacation rentals in Oshawa

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

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Guest favourite

Guesthouse in Uxbridge

4.95 out of 5 average rating, 123 reviews

Private Guesthouse in Nature minutes to Trails

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 resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Guest favourite

Home in Whitby

4.86 out of 5 average rating, 160 reviews

Cheerful 4-bedroom home with huge patio

This bright and airy 4 bedroom 3 bathroom home is perfect for a family or a friends getaway. High speed internet and full amenities. Minutes from Deercreek Golf Course, the NEW Thermëa spa, top rated restaurants, supermarkets, and shopping. Easily accessible by highway 401 or 407/412. 45-min drive to downtown Toronto. 10-min drive to Whitby GO Train station. Perfect for families, business trip or a weekend getaway, your stay here is sure to be convenient and effortless. Long-term stays welcome.

Guest favourite

Rental unit in Windfields

4.96 out of 5 average rating, 106 reviews

Family Friendly | Cozy | HOT TUB | Near UOIT

Experience comfort and convenience in this newly built 1-bedroom basement apartment with a work study, kitchen and onsite laundry. Relax in the hot tub after a busy day exploring the local farms, hiking trails, and parks nearby. Close to Ontario Tech University, banks, grocery stores, restaurants, and bars. Access to Durham Transit, GO bus & train, and located just 5 mins off highway 407. Ideal for couples or small families with a child. Book now for a hassle-free stay in Oshawa, Ontario.

Guest favourite

Rental unit in Pickering Beach

4.79 out of 5 average rating, 151 reviews

Luxurious Private Suite by the Lake

Welcome to your home away from home! This is an entire private apartment that is equipped with all your needs for a relaxing stay. It includes: Luxurious Bathroom with Soaker Tub Private Patio with Seating Roku TV with Cable, Netflix & Featured Apps Stainless Steel Appliances including Toaster, Microwave, Fridge, Keurig Coffee Maker & Kettle Air Conditioning & Heat Provided Clean Towels, Fresh Linens, Toiletries & Snacks Provided Birthday and Anniversary Packages upon Request and much more

Guest favourite

Home in Leskard

4.94 out of 5 average rating, 105 reviews

The Hive - Exclusive Full House, Nestled in Nature

The Hive Stay offers exclusive use of a retro-executive home for up to 16 people. The house features 6 bedrooms (13 beds); an expansive kitchen, large gathering area, sheltered deck & front porch, BBQ, fire pit & forested property surrounded by a nature reserve. Great for families, friends & colleagues. We are on the Greenbelt Cycling Path and very close to Ganaraska Forest Centre, Canadian Tire Motorsport Park, Brimacombe Ski Resort, Trail Tours, Tyrone Mills, Orono Park, Antiques + more.

Superhost

Cottage in Bowmanville

4.88 out of 5 average rating, 145 reviews

Super Cute & Modern 3 Bedroom Beach Bungalow

Transport Yourself To This Modern, Open Concept, 3 Bedroom Beach House & You Will Feel Like You Have Left The Country! Only An Hr From Toronto. Take In The Stunning Views Of Lake Ontario & Relax Over The Lapping Sounds Of The Waves. Enjoy Direct Access to The PRIVATE Beachfront & The Outdoor Space (Drum fire pit, Patio Set, BBQ)-It's The Perfect Urban Getaway. You Get The Entire House & Lots Of Parking Available. ABSOLUTELY NO PARTIES PERMITTED. Pls read all rules before booking. NO PETS

Guest favourite

Rental unit in Brooklin

4.91 out of 5 average rating, 242 reviews

Cozy luxury 2-bedrooms private en-suite in Whitby

Unwind in this gorgeous, modern 2 bdrms Legal /separate apartment with keyless entry. Guest can enjoyed the spacious and beautiful oasis away from home. Access to microwave, fridge, toaster, coffee maker and blender. Ignite TV premier PKG, Netflix, Air Fryer, fully functional kitchen, free 500 mbps Wifi, work desk. Close to 401, baby cot, fresh fruits. Minutes walk to the bus stop, restaurants and playground. Theatre within 10 mins , parking on premises. IT’S AN APARTMENT NOT WHOLE HOUSE

Guest favourite

Guesthouse in Pickering

4.85 out of 5 average rating, 134 reviews

Hotel 65. Our Spacious 2-Bedrm Basement w/Parking

Stunning, spacious, cozy basement apartment . Open concept living/dining room with kitchen. The larger room offers a queen bed and a futon for additional sleeps. The second has two twins that can be setup as an optional king. A TV in each room with Netflix, Prime, Disney+ and IPTV with multiple sports, North American and International channels. Many kitchen amenities. Mins to 401, Grocery, Resturants, Malls, Casinos, National Park, Toronto Zoo and only 5 minutes to GO Train. Book & Enjoy!

Superhost

Cottage in Bowmanville

4.89 out of 5 average rating, 133 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

Guest favourite

Home in Bowmanville

4.9 out of 5 average rating, 130 reviews

Luxury Waterfront Bowmanville getaway home!

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

Guest favourite

Guesthouse in Newcastle

4.86 out of 5 average rating, 170 reviews

Bee Keeper's Cabin - a very private retreat

91 acres, trails, total privacy, spring fed lake, solar power/propane heated, gas stove top, propane fridge, out-house, firepit, wi-fi ; canoe/paddleboat; 2SLGBTQ+ pets ok, Self check in and self cleaning For those who leave a "light foot print" Basic Kitchen utensils, pots, pans, are provided BUT guests must bring Bedding, WATER, coffee & press, rubber boots. We ask our guests to "try and leave the cabin better than you found it and to take all Garbage/Recycling home when leaving"

Guest favourite

Home in Bowmanville

4.91 out of 5 average rating, 144 reviews

Cozy Lakeside Modern House 4Br - Steps To The Lake

Great place to get away to the lakeside, family get together, relax, enjoy downtime. Tons of space for everyone in this 2,800 Square ft brand new modern home in the waterfront community in Bowmanville. Just a few steps to the walking trails, biking trails, beaches, playground & splash pad. Enjoy your stay with a walk when sunset or sunrise on the trails. Come and relax with a coffee by the fireplace on chilly days, or outside by the porch on warm summer days.