Apartment vacation rentals in Orangeville

A bright & chic 2 bedroom urban apartment

Come & relax...in privacy. "The Cooper" is an 833 square foot 2 bedroom that is unique & intimate. You will be on the main floor of this bungalow, with a basement apartment below you. The kitchen is amazing, complete with gas range & dishwasher. Primary bedroom has in-suite laundry, & the elegant bathroom has heated floors! Exclusive entrance and private outdoor area with BBQ. Parking out front. A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

The Bee Hive - Lower Level Raised Bungalow

Kick back and relax in this calm, stylish and super equipped space. Fully self contained and private lower apartment to our home with the hosts living above. Open plan kitchen dining living area with 1 bedroom (queen bed) and 1 shower room with 8 ft ceilings. Newly renovated, almost everything new this year ready for the 2025 season. Home from home, calm and pleasant space with all the mod cons. 50" LG Smart TV, Full sized fridge freezer, dishwasher, stove, microwave and much more - Enjoy!

Ballo 2-Bedroom Apartment

Charming 2-Bedroom in Orangeville Relax in this cozy, light-filled 2-bedroom apartment with a full kitchen, 1 washroom, spacious living area with Tv, and a dedicated workspace. Perfect for big families or 2 family’s travelling together. Extra sofa-bed available. Enjoy the private backyard with a seasonal pool and garden. Just minutes from Broadway’s shops, cafés, restaurants, the Saturday Farmers Market, and the historic Opera House. Perfect for couples, families, or remote workers.

Separate apartment with pool, on golf course.

Enjoy a newly renovated studio apartment with a private entrance and exclusive access to a serene inground pool. This cozy space is furnished with Restoration Hardware pieces and features a fully equipped kitchen, high-speed WiFi, and a patio with an outdoor barbecue—perfect for remote workers or a peaceful getaway. Situated behind Caledon Woods Golf Course, it’s just 7 minutes from the Caledon Equestrian Park, 30 minutes from Pearson Airport, and close to highways leading to Toronto.

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

Spacious Apartment 5 Minute Walk to Innisfil Beach

Book this bright, comfortable, second floor guest apartment just a short walk to Lake Simcoe & Innisfil Beach Park! Enjoy all the comforts of home in a beautiful space with high ceilings and lots of natural light. It's perfect for all seasons! We are an hour from Toronto, 20 minutes from Barrie, 15 minutes from Friday Harbour Resort, 25 minutes from Snow Valley, 30 minutes from Vetta Nordic Spa, and 15 minutes from Three Feathers Terrace Event Venue. NO CLEANING FEES!

The Evelyn Suites - Suite A - Luxury Pied-à-Terre

Hello! We are MacLean & Sarah, owners of The Evelyn Restaurant and The Evelyn Suites. Centrally located in a historic, limestone building on a Main Street in Elora, this beautifully appointed, French modern style, 2 bedroom apartment is within walking distance of everything the village has to offer, including the Elora Gorge, Shops, Restaurants and The Elora Mill & Spa. We look forward to hosting you while you relax and enjoy your stay in our luxurious pied-à-terre!

As seen on HGTV! 2-Bedroom Luxury Apartment

As featured on HGTV'’s "Income Property" with host Scott McGillivray (Season 9 Episode 2). Our guests love our "sparkling clean" luxury apartment. Cozy up by the gas fireplace, enjoy a cup of Keurig coffee or tea, or make yourself a gourmet meal in our spotless, fully equipped kitchen. Whether you're working "from home" or enjoying a much-needed getaway, everything is right at your fingertips and you will feel right at home! Stay for a few days or a few weeks.

Brick House on Broadway - Butler Unit

The Brick House on Broadway - The Butler Unit. Stay in a beautifully restored 1-bedroom Butler Unit, rich in history - part of the property owned by Lester B. Pearson's grandparents. Enjoy a peaceful stay in walking distance of Orangeville's downtown shops and restaurants, close to the Hockley Valley hiking trails. Cozy, private, and full of charm - the perfect escape for nature lovers, history buffs, or a romantic getaway.

The Elora Riverview Flat

Enjoy your morning coffee looking out towards the grand river and just past that, see all the unique buildings that make up Mill St. From the Mill to the main St. the view is complete and is yours enjoy. Also on this level you have a complete kitchen and a cozy comfortable space to watch your favorite Netflix Shows. Each floor has a bathroom the main bathroom is on the second floor where your Two bedrooms are.