As the winter starts to really settle into Toronto, our brains do what they always do: start planning the escape. While we all love the classics, there’s a new wave of design-forward boutique stays turning Ontario’s cutest towns into full-on winter destinations.
These aren’t just “somewhere to sleep” hotels. They’re tiny, chic, obsessively curated properties with fireplaces, Nordic spas, natural wine bars and lobby lounges that feel like your most stylish friend’s living room. And because a good winter getaway is about the whole vibe, each of these stays comes paired with the best nearby things to do: Christmas markets, frozen waterfalls, pizza worth braving a snowstorm for, cozy cinemas and wine-soaked evenings.
Here’s where to book your next chic winter weekend in Ontario — and exactly what to do once you’ve dropped your bags.
Elora: Tiny heritage village, big boutique energy
Stay at: Kat Florence Hotels & The Ayrshire Hotel
Elora in winter feels a bit like a movie set: limestone buildings, the Grand River running past, snow-dusted roofs and twinkly lights down every side street. It’s already a classic getaway town — but two new boutique hotels are quietly making it the place to escape from Toronto this season.
Kat Florence Hotel
Set in a meticulously restored 1840s stone building that once housed the old Commercial Hotel, the Kat Florence Hotel is pure heritage-meets-high-luxury. Think original stonework and historic balconies, but layered with modern farmhouse kitchens, designer appliances, plush bedding and spa-level bathrooms. Suites feel more like high-end residences than hotel rooms — especially the multi-bedroom Diamond House with its private outdoor hot tub and fire pit.
The vibe is very “quiet luxury in a storybook village”: earth-toned textiles, hand-crafted details, fireplaces, big windows and that soft, flattering mood lighting that makes you want to pour a glass of wine and never leave your robe.
Why choose Elora for your weekend getaway? Elora Christmas Market runs right next door, with cedar chalet vendors, 80,000+ lights and outdoor fire tables for lingering under the stars. A Nordic spa opens for the season, so you can do the full hot–cold–hot circuit after the market and then shuffle back to your suite. Suites have full kitchens or kitchenettes, so you can stock up on local goodies and lean into the “we live here now” energy.
Make it a full Elora weekend by: grabbing sourdough pizza at Tony’s Sourdough Pizzeria, ducking into The Gorge Cinema — a tiny heritage movie theatre that feels straight out of Gilmore Girls — and wandering the lit-up streets for peak small-town-at-Christmas hallmark movie feels.
The Ayrshire Hotel
A few minutes away, The Ayrshire takes over a restored 1860s mansion and leans into cozy, grown-up boutique charm. Ten suites in the main house and six more in a nearby guesthouse keep things intimate: think king beds, fireplaces in many rooms, luxe bath products and carefully layered historic details.
This is your hotel for curling up by the fire with a bottle of wine and a book. Guests are right in the village core, so you can stroll to cafés, shops and the gorge, then retreat to your turreted room when the snow starts to really fall.
Burlington: A faux-British waterfront escape
Stay at: The Pearle Hotel & Spa
If you want to feel like you’ve hopped over to a chic coastal town in the UK — without the red-eye — Burlington in winter is wildly underrated. Downtown comes alive with brick-lined streets, a classic red phone box, a winter market and lake views that feel far more European than GO-train-adjacent.
Anchoring it all is The Pearle Hotel & Spa, a design-forward waterfront stay that technically belongs to Marriott’s Autograph Collection but reads way more boutique than chain. The look is Ontario lake house meets glossy design mag: white-oak panelling, sculptural staircase, linen and stone textures, soft blues and creams, and floor-to-ceiling windows staring straight at Lake Ontario.
Rooms range from airy studios to sprawling suites with terraces and soaker tubs, but all feel like polished, minimal coastal apartments rather than generic hotel boxes.
Spend a slow morning at The Pearle Spa with a hammam-style steam, a swim in the indoor pool and a long, ritual-y treatment. Linger over dinner at Isabelle, the hotel’s Mediterranean-inspired restaurant that leans into coastal flavours and local Ontario ingredients. Wander Burlington Village Square and the downtown core: cobblestones, twinkly lights, red brick and English-phone-box photo ops. Add a winter hike at Mount Nemo Conservation Area or a cozy culture stop at Ireland House Museum to complete the mini U.K. countryside illusion.
Caledon: Kate Winslet in The Holiday
Stay at: The Liberty Inn
The Liberty Inn in Caledon is the closest thing Ontario has to Kate Winslet’s cottage in The Holiday. The 1850s stone building has lived many lives — post office, general store, speakeasy — and now, after a years-long restoration, it’s a tiny Nordic spa inn with just five suites and a whole lot of cinematic charm.
Inside, the look is all countryside cottage with creamy palettes, soft linens, four-poster beds, blue cabinetry and handmade tiles and ceramics everywhere. Step outside and you’re in a private woodland spa circuit with cedar hot tub, sauna and cold plunge under string lights and trees. It’s the kind of place where you wear a robe all day and sincerely mean it.
To complete the winter staycation drive over to Belfountain for a latte at Higher Ground Café, which turns into the coziest locals’ hangout once the tourists thin out. Warm up with cider and comfort food at Spirit Tree Estate Cidery. Hunt for treasures at Inglewood Antiques, or head to Alabaster Acres for a tucked-away farm Christmas market.
Newmarket: Heritage post office turned chic stay
Stay at: The Postmark Hotel
Newmarket’s Main Street seriously leans into Hallmark movie territory in winter — and now it has a boutique hotel to match.
The Postmark Hotel takes over a 1914 post office, keeping the red-brick façade and clock tower while completely reimagining the interiors as a modern, art-forward stay. Inside, you’ll find 55 unique rooms with high ceilings, huge windows, Canadian art and a mix of industrial and vintage touches. Some rooms even come with private ground-floor terraces, so you can step straight out into the snowy air.
The hotel doubles as a social hub: there’s The Lobby, an all-day café/bar made for coffee, cocktails and pre-dinner hangs, and Overlea, a rooftop restaurant with big views over Main Street and a farm-to-table menu.
Don’t miss all the essential spots the city has to offer this winter. Vintage Peony transforms into a full-blown holiday fantasy filled with ornaments, décor and gifts. Stop into Conscious Find for second-hand fashion that’s beautifully curated. Main Street’s indie shops and bakeries (do not skip butter tarts at The Maid’s Cottage) make it very easy to “just pop in” and somehow finish all your gift shopping.
Collingwood: Ski, spa and small-town cool
Stay at: Somewhere Inn Collingwood and The Dorchester
Collingwood is already a no-brainer in winter — Blue Mountain is minutes away, and there’s snow everything. But the boutique scene here has levelled up.
Somewhere Inn
Somewhere Inn is Collingwood’s best kept secret, a 100-year-old hotel turned moody, modern retreat: vintage loungers, restored hardwood, king beds and rooms designed for lingering (no TVs, on purpose). There’s an on-site thermal circuit with sauna and cold plunge, plus Brooky’s Wine Bar & Garden Patio downstairs, which acts like the lobby’s living room: coffee in the morning, snacks and natural wine at night.
The Dorchester Hotel
A few steps away, The Dorchester Hotel brings Roaring ’20s energy to historic Hurontario Street — all restored brick, 1920s-inspired interiors and big plans for a lively lobby bar. Rooms are styled to feel like an elevated downtown apartment: studios and suites with thoughtful finishes and that backstory-rich Collingwood history baked into the walls.
Your winter weekend can look like skiing, snowboarding or tubing at Blue Mountain — or my personal favourite, leaning into a chalet day. Try a steamy afternoon at Scandinave Spa if you prefer your winter sports in towel form. Enjoy dome dining and cider flights at Thornbury Craft. Or go snowshoeing at Scenic Caves Nature Adventures before retreating back to the sauna and wine bar.
Prince Edward County: Off-season, on-point
Stay at: The Royal Hotel Picton
In summer, Prince Edward County is all sunshine, patios and winery-hopping. In winter, it’s quietly dreamy — and The Royal Hotel is the place to lean into that off-season magic.
The lovingly restored 1879 railway hotel has been reborn as a 33-room boutique property split between the historic main building and a Scandi-inspired Annex. Rooms are named after local apple varieties and come with tartan-inspired tiles, soaker tubs, fireplaces in many suites and the kind of tactile textiles (plush robes, layered bedding) that make you consider accidentally sleeping through your dinner reservation.
On-site, you’ve got a full spa with sauna and gym, casual–elegant dining from a chef who leans into local farms, including the owners’ own property and a lobby café (The Counter Bar) slinging pastries, coffee and pantry goods. Outside, you’re perfectly placed to hit winter winery tours — bubbles, reds, icewine, the works. Visit All My Friends Beer Co. for a low-key pint, or check out Wander the Resort for their festive Wanderland market and light displays. Book an alpaca walk at Andara Gallery for a very on-brand PEC photo op.
Hamilton: Private spa suites and frozen waterfalls
Stay at: The High Acre
Ten minutes from where the owner grew up, a 150-year-old Victorian farmhouse has been transformed into The High Acre — four suites, each with its own infrared sauna, steam room, soaker tub, king bed and fireplace.
The design brief was “a little Europe in Dundas”: restored original beams and floors, French doors, moody murals, a reception bar built from salvaged timber and record players in every room. Kitchens stocked with coffee, tea, eggs and ready-to-bake croissants make mornings feel very Paris terrace.
Winter itinerary includes chasing frozen-waterfall views at nearby Tiffany Falls, Webster’s Falls, Devil’s Punchbowl and more. Then, warm back up in your personal spa suite (yes, really) with a DIY hammam session and long bath and head into Hess Village or downtown Hamilton for dinner and drinks. End the day off as you sample the area’s growing cider scene with stops at local cideries.
Niagara-on-the-Lake: Scottish country fantasy
Stay at: The Scotsman Hotel
Niagara-on-the-Lake already looks like a Christmas village for most of December — wreaths, garlands, horse-drawn carriages, the works. The newest addition to the scene is The Scotsman Hotel, inspired by the original in the Scottish countryside. The tiny, Lori Morris–designed five-suite property feature jewel tones, rich fabrics, clawfoot tubs, fireplaces and a Champagne Room and Whiskey Room downstairs for pre- and post-dinner lounging.
Expect bar carts you can stock with Niagara wine, candlelit lounges and a patio with fireplaces that stay lit until the last guest heads upstairs.
Do Niagara-on-the-Lake properly by skating at the outdoor rink in the gardens at Pillar and Post, then grabbing hot chocolate and soft pretzels at The OutPost. Get delightfully lost in a year-round Christmas shop, Just Christmas and grab some warm chimney pastries at Budapest Bake Shop. Don’t forget to plan a return trip for the Niagara Icewine Festival in January.
