The Best Weekend Getaways from Toronto: Discover Hamilton’s Hidden Luxury Boutique Hotel (Winter Edition)

As winter settles over Southern Ontario, Torontonians begin craving cozy escapes, romantic snowy weekends, and simple getaways that don’t involve long drives or complicated planning.

Suppose you’re searching for the best weekend getaways from Toronto. In that case, there is no better choice than Hamilton and Ancaster — home to scenic winter trails, incredible restaurants, local breweries, holiday charm, and a luxury boutique hotel that feels like a hidden gem: The Barracks Inn.

Just one hour from Toronto, this historic stone hotel combines comfort, elegance, and small-town charm — creating the perfect winter retreat.

Why Hamilton Makes the Best Winter Weekend Getaway from Toronto

Hamilton has quietly become one of Ontario’s most compelling winter destinations. While it once had a reputation as an industrial town, today it offers:

• Snow-covered waterfalls
• Scenic conservation areas
• A thriving restaurant & brewery scene
• Historic villages like Ancaster & Dundas
• Winter festivals and holiday markets

Best of all, you’re not spending hours in traffic or fighting for parking at overcrowded tourist spots. Hamilton delivers beauty, charm, and relaxation without the fuss.

Stay in Style: The Barracks Inn — Hamilton’s Luxury Boutique Hotel

For a winter getaway, the hotel you choose matters. You want warmth, character, and the kind of comfort that makes you want to stay inside.

At The Barracks Inn, you’ll find:

• Fireplaces in select suites — perfect for cozy evenings
• Spa-inspired bathrooms with soaker tubs & rainfall showers
• King-sized beds with luxury linens
• Complimentary breakfast each morning
• Historic 19th-century architecture blended with modern amenities
• Quiet village atmosphere just minutes from Hamilton’s best attractions

It’s one of the most unique boutique hotel experiences in Southern Ontario and a defining feature of the best weekend getaways from Toronto.

Winter Activities & Things to Do Near The Barracks Inn

Hamilton and Ancaster offer endless winter activities ideal for couples, friends, or solo travelers.

1. Chase Winter Waterfalls

Hamilton’s waterfalls are breathtaking year-round, but winter turns them into quiet, snowy masterpieces.

Top picks near the Inn:

• Tiffany Falls — minutes away
• Webster Falls
• Sherman Falls
• Dundas Peak — stunning winter vistas

Beautiful for photography, peaceful walks, and romantic morning outings.

2. Explore Winter Villages & Holiday Lights

Ancaster Village, Dundas, Locke Street, and Westdale come alive in winter with:

• Festive lights
• Artisan markets
• Boutique shopping
• Cafés serving hot chocolate and fresh pastries

These neighbourhoods feel worlds away from Toronto’s pace.

3. Warm Up at Local Breweries

Winter is brewery season, and the region offers exceptional choices:

• Shawn & Ed Brewing Company (Dundas)
• Fairweather Brewing
• Merit Brewing
• Collective Arts Brewing

Perfect for flights, wood-fired pizza, and cozy mid-day breaks.

4. Treat Yourself to a Spa Day

Winter = self-care. Luckily, you’re minutes from excellent spas:

• The Spa at Ancaster – full spa menu in a heritage home
• Serenity Spa & Wellness – holistic treatments
• Pure Skin Studio – rejuvenating skincare

Pair a relaxing morning treatment with a cozy afternoon in your suite.

5. See a Show or Explore Local Art

Hamilton’s entertainment and arts scene continues to grow. Depending on your weekend, you might enjoy:

• A concert at the new TD Coliseum
• A performance at Ancaster Memorial Arts Centre
• Galleries on James Street North

Hike in the morning, dine in the evening, and end the night with live entertainment — it’s a perfect Toronto getaway without the travel stress.

Winter Wine Country: Explore Niagara-on-the-Lake & Local Wineries

One of the biggest perks of a winter getaway at The Barracks Inn? You’re just 35–45 minutes from Niagara-on-the-Lake, one of Canada’s most celebrated wine regions.

Why Niagara wine country is magical in winter:

• Snow-covered vineyards create enchanting scenery
• Icewine harvest and tastings begin
• Wineries are calm, intimate, and beautifully decorated
• Many estates offer fireside lounges & candlelit experiences

Popular wineries nearby:

• Peller Estates – iconic icewine, elegant tasting rooms
• Trius Winery – sparkling wines & immersive experiences
• Two Sisters Vineyards – luxurious estate with incredible food
• Ravine Vineyard – cozy farmhouse charm
• Stratus Vineyards – bold, modern, architecturally stunning

Whether you’re planning a romantic escape, a friends’ weekend, or a relaxing winter retreat, adding wine country to your itinerary makes your stay even more memorable.

And at the end of the day, return to The Barracks Inn, your warm and welcoming luxury boutique hotel, to unwind by the fire and enjoy the comfort of your elegant suite.

Where to Eat: The Best Winter Restaurants in Hamilton, Ancaster & Dundas

Hamilton’s food scene is one of the biggest reasons travelers choose weekend getaways Hamilton over more predictable destinations.

Downtown Hamilton Restaurants

Here are must-try spots for dinner before or after exploring the city:

• Noir on Locke – intimate, stylish, and perfect for winter date nights
• Lobby Hamilton – craft cocktails, modern dining, and cozy ambiance
• The Mule – tacos, tequila, and energetic atmosphere
• Conversate Steak & Seafood – premium cuts, seafood towers, and upscale dining
• Plank on Augusta – craft cocktails + small plates
• Electric Diner – retro comfort food, brunch, and cocktails

These make Hamilton a top choice for best weekend getaways from Toronto with a foodie twist.

Ancaster Restaurants (Minutes from The Barracks Inn)

• Coach & Lantern – classic pub atmosphere with a fireplace
• Brassie Pub – casual, warm, and great for winter comfort food
• Mist Restaurant & Lounge – stylish dining with global flavours
• Ancaster Mill – fine dining beside a snowy waterfall
• Cavallo Nero – elegant Italian cuisine

All perfect for a cozy winter meal just steps from your boutique hotel.

Dundas Restaurants (10 Minutes Away)

• Collins Brewhouse – historic charm + hearty plates
• Shawn & Ed Brewing Company – wood-fired pizza, beer flights
• Bohemian Beirut – Lebanese fusion, warm spices for winter
• Betula – upscale seasonal dining
• The Burnt Tongue – famous soups that hit perfectly on cold days
• Bangkok Spoon – Thai comfort dishes

Whether you want a romantic dinner, casual drinks, or warm winter comfort food, you’ll find exceptional choices moments from your boutique hotel.

Why Toronto Travelers Love Hamilton for Winter Weekends

Short, easy drive

• No long commutes — arrive relaxed, not exhausted.

Affordable boutique luxury

• More value and charm than Muskoka or Blue Mountain hotels.

Endless winter activities

• Waterfalls, wineries, spas, restaurants — all close to each other.

A truly unique hotel experience

The Barracks Inn offers the perfect blend of charm, warmth, and upscale comfort.

Plan Your Winter Getaway Today.

If you’re looking for one of the best weekend getaways from Toronto, winter is the perfect time to explore Hamilton and Ancaster. With snowy trails, cozy dining, local breweries, and nearby wine country, the region delivers a rich, relaxing, and romantic winter experience.

And at the heart of it all sits The Barracks Inn — a luxury boutique hotel where fireplaces, elegant suites, and warm hospitality create the ultimate winter escape.

Book your stay at The Barracks Inn and discover Hamilton’s most underrated winter destination.