Holiday rentals in Oshawa

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Top-rated holiday rentals in Oshawa

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

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Guest favourite

Bungalow in Pickering

5 out of 5 average rating, 30 reviews

Beachy bungalow

Welcome to the Beachy bungalow in the sought after bay ridges area. This two bedroom one bathroom home is located a short walk from the marina, Frenchman’s Bay and local restaurants. It comes equipped with a chefs kitchen; including a gas stove, two bedrooms each with a queen bed and a beautifully spacious bathroom. After a long day by the water come back home to your own secluded backyard oasis. This home is also located a short drive to the 401, 10-15 minutes from the casino and Toronto Zoo.

Guest favourite

Guest suite in Uxbridge

4.78 out of 5 average rating, 9 reviews

Hilltop Getaway|Scenic Views |Back to ForestTrails

Escape to this stunning hilltop 2-bedroom Airbnb, nestled on 22 acres of beautiful woodland just 2 minutes from Lake Ridge Ski Resort.Enjoy breathtaking panoramic views of the mountains from your private retreat, perfect for those seeking both relaxation and adventure This cozy unit is ideal for hikers, with direct access to Glen Major Forest and scenic trails right at your doorstep There is no living room, you will have 2 bed rms, 1 washroom and a kitchen This unit is a portion of main cottage

Guest favourite

Guest house in Uxbridge

4.96 out of 5 average rating, 137 reviews

Guesthouse in nature mins to Ski hills and 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 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!

Superhost

Bungalow in Oshawa

4.78 out of 5 average rating, 59 reviews

Luxurious Modern Getaway 3BD 2BT Near 401

Less than 3 mins drive to 401! Welcome to this splendid vacation home, a true gem offering the perfect blend of comfort and adventure. W/ 3 bedrooms and 2 bathrooms, this smoke-free retreat accommodates up to 8 guests, providing ample space for everyone make cherished memories. Be delighted with the proximity to fishing spots/marina and embrace the excitement of the surrounding area as you embark on a 7- min drive to Lakeview Park knowing that convenient onsite parking awaits upon your return.

Superhost

Cottage in Bowmanville

4.83 out of 5 average rating, 156 reviews

Waterfront Beach House Oasis - All Season Hot Tub!

Welcome to our serene waterfront sanctuary! This stunning 4-bed, 3-bath retreat is the perfect escape just outside the city. Enjoy unobstructed lake views, sunsets, kayaks, fire pit, BBQ, and a year-round hot tub. Relax indoors with a movie or on the private pebble beach. Explore nearby Darlington conservation areas for hiking and wildlife. Our home offers everything you need for the ultimate urban getaway. Whether you seek relaxation, adventure, or natural beauty, your perfect retreat awaits!

Superhost

Home in Whitchurch-Stouffville

4.9 out of 5 average rating, 30 reviews

Place Perfect for Fishing in Stouffville

This little gem its back onto musselman’s Lake, with breathtaking views regardless of sunrise or sunset. Perfect for a family getaway or spend a romantic date with your love one. It’s very cozy no matter which season of the year. Come and explore all the beauty of nature has to offer lots of scenic trails and lots of beautiful golf courses in the area. IMPORTANT: enjoy unlimited water fun!!! It has 2queen size bed and 1 king size bed with 2 bedroom and 1 bathroom. Dining room and a kitchen.

Guest favourite

Home in Bowmanville

4.88 out of 5 average rating, 72 reviews

*Lakeside Retreat: Viva La Vida*

Modern Aesthetic meets Lakeside Luxury with Close Proximity to a lot of Activities! - 3 Beds/1.5 Bath to sleep 8 - 2 Queen size beds & 4 single bunk bed spaces - 60'' Flat-screen TV ( Amazon Prime, Netflix, Smart TV) - Fully equipped kitchen with modern appliances - Coffee Machine - Cozy living room with ample seating - Outdoor furniture for lakeside relaxation - In-suite Washing machine & Dryer - 1000 MBPS Wi-Fi - Washer and dryer for your convenience - 3 car parking space - Large patio

Guest favourite

Villa in Bowmanville

4.91 out of 5 average rating, 137 reviews

Grand Waterfront Retreat – Under 1hr from Toronto

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!

Top guest favourite

Home in Courtice

5 out of 5 average rating, 21 reviews

Home away from Home

Private, relaxing, bright one bedroom , 900 sq ft walk-out basement apartment. This home is nestled on a quiet court which backs on to a forested ravine. Enjoy relaxing on the backyard patio with your morning coffee or evening wine and enjoy the tranquil nature setting. The home features a beautiful kitchen, large breakfast island, open concept living room with work space, cozy gas fireplace, large bedroom with walk-in closet and a beautiful 3pc bathroom with frameless glass shower.

Superhost

Home in Ajax

4.77 out of 5 average rating, 44 reviews

HiddenGem: home away from home

This luxurious semi-detached With 2 en suite washroom house sounds like a wonderful place to stay! The convenient location near major highways and shopping plazas makes it ideal for guests looking to explore the area. The well-equipped interior with three luxurious bedrooms, smart TV, high-speed internet, and a full kitchen provides a comfortable and relaxing environment. The attached one-car garage accessible from inside the house adds a convenient touch for guests with vehicles.

Superhost

Home in Oshawa

5 out of 5 average rating, 4 reviews

Heaven Bliss: Stylish 4B/2.5B, Kitchen, Parking!

Experience ultimate comfort and convenience at our Heavenly Bliss - book now before spots fill up! ★ Fully equipped with luxurious furnishings ★ High-speed internet up to 300 Mbps ★ Free dedicated parking spot ★ Smart TVs in bedroom and living room ★ Luxurious queen-sized beds with premium mattresses ★ Full kitchen with all essentials ★ Dedicated workstation for remote work or email ★ Convenient location near the beach, shops, restaurants, and outdoor recreation ★ And MANY more!

Top guest favourite

Flat in Oshawa

5 out of 5 average rating, 37 reviews

Modern & Cozy | Delpark Homes Centre | UOIT

Step into the comfort of this newly built, 2-bedroom basement apartment, the epitome of luxury in the family friendly Oshawa neighborhood. Located within minutes to Delpark Homes Centre, grocery stores, Farmboy, Costco, restaurants, bars, plenty of golf courses, local farms, hiking trails and parks. Convenient access to highway 407, Durham Transit, GO bus & train. Book now and experience the comfort and convenience of our stylish retreat.