The Coziest Hotels to Book For Your Winter Staycation

As we settle into the winter season, we’ve got just one thing on our minds: getting cozy. Plus, the holidays often leave us feeling like we need a vacation from a vacation, so what better time to start planning your cozy winter staycation for the new year?

If your idea of a restful getaway is less about the getting away and more about the room service, crisp linens on a king bed, and a hotel restaurant nightcap, we’ve got you covered. These are the best hotels to book your winter staycation, so get on it—stat.

Drake Devonshire

The beloved Drake Devonshire in Prince Edward County certainly needs no introduction, and is one of our favourite Canadian hotels for a cozy staycation, but it did add some cool features to its guest experiences offerings this year (with a larger expansion planned for 2025). For now, you can enjoy a pickleball court and observation area, a stunning 10-person lakeside sauna, beach decks and a swimming area, new gardens and an art walk, and finally a games area including an outdoor ping pong table and boules court. Because what’s a staycation without an abundance of activities to choose from, anyway?

The Postmark Hotel

If a short trek outside of the city is part of your staycation criteria, might we suggest The Postmark Hotel? Originally built as a post office in 1914, the space has been reimagined into a delightful and colourful boutique hotel in Newmarket, Ontario (about one hour north of Toronto). The stunning hotel, courtesy of Archive Hospitality Group, the group behind Toronto’s Gladstone House and The Broadview Hotel, opened its doors to the public this past summer and is located on Newmarket’s charming Main Street. Featuring spacious rooms (each of which has its own carefully curated selection of Canadian artwork), four event spaces and two restaurants (The Lobby and Overlea), there’s no shortage of cozy vibes here.

Somewhere Inn

A welcoming wave of local charm is the first feeling that hits you upon entering Collingwood’s Somewhere Inn. Nestled on a tranquil tree-lined street, this restored century home turned boutique hotel is the ultimate retreat for a wellness weekend. Full of bespoke furniture and curated art, each vintage-inspired room is brimming with character and calm. Outside, enjoy an intimate spa-like experience with a sauna-cold-plunge circuit and communal fire pit before heading to the lobby for organic wine and specialty snacks. And if you’re looking to explore Collingwood through a self-care-themed itinerary, the Somewhere Inn staff is ready with recommendations — from guided snowshoe excursions to full-body massages.

Sofitel

Planning a vacation in Montreal? Look no further than Sofitel Montréal Golden Mile. Earlier this year, the luxury hotel chain announced a refurbishment project of its flagship location in downtown Montreal, which opened 20 years ago. The three-phase reno project includes everything from guest rooms to common spaces to the hotel restaurant. Updates include an upcoming renovation to Renoir restaurant featuring a new bar area, a newly refurbished common area, and finally the finished guest rooms which will be ready in spring 2025. Lots to look forward to and plenty of opportunities to unwind.

The CAPE

The truly majestic and stunning The CAPE in Picton, Ontario is a sight to behold. The landmark, a historic mansion-turned-hotel features four boutique-style suites, along with a ballroom and three event spaces, and is often used as a wedding venue thanks to its elegant and spacious feel. Rooms can be booked individually, or if you’re planning a visit with the whole family (and then some), the entire house can be booked. The CAPE recently added breakfast in bed to their menu, which seals the deal for any staycation, don’t you agree?

Wander the Resort

Prepare for a staycation you won’t soon (or ever) forget. Welcome to Wander the Resort, breathtaking lakefront cabin retreat located in the heart of Prince Edward County. Featuring 10 zen, family-friendly cabins furnished with locally sourced and sustainable furniture and decor, Wander opened in 2021 and has been garnering global acclaim (and awards) since then. The cabins’ Nordic designs feature light-coloured wood, and accents of cream, black, and grey. (Told ya: it’s zen.) Gather at Wander, the resort’s onsite restaurant, opened last year, and the highly anticipated, 10,000 square foot Wander the Spa, the first-ever lakefront Nordic spa in Ontario, is opening imminently. (Pre-sale passes can be purchased now.) If a meditative, rejuvenating staycation is on your mind, this is just the place for you.

The St. Regis

It’s a classic for a reason. Although the hotel is located right in the city’s downtown core, The St. Regis Toronto offers such a premium level of elegance that the hustle and bustle beneath you (31 floors beneath you, to be exact) will quickly fade away as you enjoy a truly luxurious staycation. Plus, with several fun and festive-themed dining, suite and spa offerings, the hotel is positively buzzing with Christmas spirit this holiday season. Enjoy a lavish brunch or dinner at LOUIX LOUIS courtesy of a special menu filled with an elevated array of classic seasonal favourites. Then, treat yourself to the gift of relaxation with the spa’s limited-time Christmas Bliss Duo and Merry & Bright Escape packages. The fun doesn’t stop there either, ring in 2025 right with the New Year’s Eve grand hotel and dinner package, which includes party favours, live performances and countdown celebrations — what better way to pass the time until the ball drops?

W Hotel

Step into a unique and opulent festive escape this holiday season with a magical staycation at W Toronto. The Yorkville hotel is the spot to visit for a magnetic atmosphere filled with dynamic programming, live music, mixology and much more as you and your loved ones celebrate the most wonderful time of the year. And, if you have room in your schedule for just a little more luxury, the hotel has teamed up with Parisian beauty brand Guerlain to provide a one-of-a-kind French-themed High Beau-Tea experience. In celebration of the brand’s newly relaunched Rouge G Lipstick line, beauty lovers will be treated to a menu of Parisian-infused bites inspired by some of Guerlain’s most iconic products. Reserve now to get a taste of a truly unique experience.