Southern Ontario offers a wealth of high-end escapes, each with its own distinct charm – from serene wine country retreats to iconic lakeside resorts. For Oakville residents, these destinations are an easy drive away, making them ideal for luxurious weekend getaways.
Niagara-on-the-Lake (1 hour drive)
Niagara-on-the-Lake is Ontario’s premier wine country destination, where tree-lined streets host historic buildings, elegant boutiques, gourmet restaurants, and world-renowned wineries. The area is also home to the Shaw Festival, offering acclaimed theatre productions throughout the season.
Where to stay:
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Oban Inn & Spa
An intimate boutique hotel overlooking Lake Ontario, featuring beautifully landscaped gardens, a heated outdoor saltwater pool, and a holistic spa offering facials, massages, and wellness rituals. Guests can dine at the refined Oban Restaurant or walk to nearby wineries for tastings in the afternoon sun.
Visit: https://www.obaninn.ca
Where to eat:
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Treadwell Cuisine – Seasonal farm-to-table fine dining with an extensive Niagara wine list.
Visit: https://www.treadwellcuisine.com -
The Restaurant at Peller Estates – Elegant winery restaurant offering refined regional cuisine and wine pairings.
Visit: https://www.peller.com/winery-restaurant.html
Cambridge (~45 minutes drive)
Cambridge offers a mix of heritage stone architecture, scenic walking trails along the Grand River, and quiet sophistication. It is home to the region’s most celebrated luxury country house hotel.
Where to stay:
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Langdon Hall Country House Hotel & Spa
Nestled on a wooded estate, Langdon Hall is an exclusive Relais & Châteaux property featuring 60 uniquely appointed rooms and suites, each with antique furnishings and elegant charm. Guests enjoy farm-to-table dining from Chef Jason Bangerter, an award-winning wine cellar, a European-style spa, croquet lawns, and forest trails. Afternoon tea on the terrace overlooking manicured gardens completes the quintessential country retreat.
Visit: https://www.langdonhall.ca
Where to eat:
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Langdon Hall Dining Room – Fine dining with a Relais & Châteaux experience, led by Chef Jason Bangerter using estate gardens and local producers.
Visit: https://www.langdonhall.ca/eat-drink/#dining-room -
The Easy Pour Wine Bar – Upscale wine bar with small plates and craft cocktails in a restored heritage building nearby.
Visit: https://www.theeasypourwinebar.com
Elora (1 hour 15 minutes drive)
Area Overview:
Elora is a picturesque village renowned for its artisan shops, cafes, and the dramatic Elora Gorge with its limestone cliffs and rushing waters.
Where to stay:
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Elora Mill Hotel & Spa
This historic stone mill, perched above the Grand River falls, has been transformed into a luxurious hotel offering gorge-facing rooms, a rooftop pool with panoramic views, and an indulgent spa featuring hydrotherapy, massages, and treatments inspired by the surrounding landscape. The on-site restaurant showcases refined Canadian cuisine using seasonal local ingredients.
Visit: https://www.eloramill.ca
Where to eat:
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Elora Mill Restaurant – Elevated Canadian cuisine with panoramic views over the Grand River and Elora Gorge.
Visit: https://eloramill.ca/restaurant/ -
The Evelyn – Modern bistro with elegant interiors offering globally inspired plates and creative cocktails.
Visit: https://theevelynrestaurant.com
Prince Edward County (2.5 hours drive)
Known as PEC, this region has become Ontario’s trendiest rural escape, famed for its wineries, cideries, contemporary art galleries, and Sandbanks Provincial Park with its expansive sandy beaches.
Where to stay:
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Drake Devonshire (Wellington)
A boutique lakeside hotel combining urban design sensibilities with rustic charm. Rooms feature contemporary art, custom furnishings, and waterfront views. The restaurant offers creative farm-to-table dining with locally sourced ingredients, while outdoor fire pits, curated experiences, and seasonal events create a lively yet laid-back atmosphere perfect for stylish getaways.
Visit: https://www.thedrake.ca/drakedevonshire/
Where to eat:
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The Drake Devonshire Dining Room – Farm-to-table cuisine with lake views and a focus on local seasonal ingredients.
Visit: https://www.thedrake.ca/drakedevonshire/food-drink/ -
Flame + Smith (Bloomfield) – Upscale wood-fired dining featuring ethically sourced meats and seafood, and natural wines.
Visit: https://flameandsmith.com
Muskoka (2.5 hours drive)
Muskoka is Canada’s iconic cottage country, known for its rocky Canadian Shield landscapes, towering pines, and pristine lakes dotted with grand cottages and boathouses.
Where to stay:
- JW Marriott The Rosseau Muskoka Resort & Spa (Minett)
Overlooking Lake Rosseau, this expansive luxury resort offers elegantly appointed suites, a full-service spa, indoor and outdoor pools, fine dining at Teca and The Muskoka Chophouse, and year-round activities from kayaking to snowshoeing. Guests can relax by the lakefront fire pits or take in stunning sunsets from their private balconies, enjoying all the hallmarks of classic Muskoka luxury.
Visit: https://www.marriott.com/en-us/hotels/yqajw-jw-marriott-the-rosseau-muskoka-resort-and-spa/overview/
Where to eat:
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Teca at JW Marriott – Fresh Italian cuisine with an open-kitchen concept and fine wine pairings.
Visit: https://www.marriott.com/en-us/hotels/yqajw-jw-marriott-the-rosseau-muskoka-resort-and-spa/dining/ -
Crossroads Restaurant (Rosseau village) – High-end dining with seasonal menus highlighting local ingredients in an elegant cottage-style setting.
Visit: https://crossroadsrosseau.com
