Valentine’s Weekend in Toronto: Gladstone House, Broadview Hotel and Postmark Hotel
Valentine’s Day lands on a Saturday this year, and with Family Day following, you’ve got a full long weekend ahead. If you’re in or around Toronto and want a night (or two) away that feels thoughtful without being over-the-top, three boutique hotels have put together packages worth considering. Here’s what each one is offering February 13–15, 2026.
Gladstone House – West Queen West
Gladstone House sits in the heart of West Queen West, surrounded by galleries, bars, and restaurants you’d probably end up at anyway. The building has character: exposed brick, local art on the walls, and ambient lighting that changes with the day.
For food, the new restaurant Cassette has Valentine’s features like braised beef or lamb shank and truffle gnocchi. They’re also doing half-priced bottles of wine and a special cocktail all weekend. The café next door serves brunch, and on Sunday, there’s a ticketed R&B brunch called The Soul Suite with a live DJ and musician (two seatings: 11 a.m. and 2 p.m.).
Live music runs all weekend. Friday night, Mira Méla and her quartet play after dinner. Saturday, guitarist Leo Orlov performs during service. Sunday evening, Meagan De Lima does a full Olivia Dean tribute show with a live band.
If you stay over, you can add late checkout, a bottle of bubbly in the room, or get discounts for booking three nights or more. This is the spot if you want energy and live music without leaving the building.
Broadview Hotel – Riverside / Leslieville
Broadview Hotel is the restored red-brick landmark at Queen and Broadview. The rooftop alone makes it worth a visit: a 360-degree glass facade and one of the best skyline views in the city.
They’re keeping things simple but indulgent. Oysters and bubbly flow all weekend at both the rooftop bar and the ground-floor bistro. Brunch is on too, so you can start with bubbles in the morning and keep going upstairs later.
Room add-ons mirror Gladstone’s: late checkout, in-room bubbly, and discounts for stays of three nights or longer. They also have a Valentine’s Room Package that bundles everything together. If you like views and oysters, this one’s hard to beat.
Postmark Hotel – Newmarket
Postmark is farther out, about an hour north on the 404, in a 1914 heritage building on Newmarket’s Main Street that used to be the post office. The rooftop restaurant Overlea is the main draw.
Friday through Sunday, they’re running a three-course “Made for Two” prix fixe menu for $95 per person. It’s designed for sharing, with seasonal ingredients and optional wine pairings. The rooftop has wraparound terraces, so the setting feels romantic.
For stays, they have a “Room For Two” package with options like a dozen roses, housemade chocolates, bubbly, and the same 15% discount for three or more nights.
It’s the quietest of the three, perfect if you want to get out of the city for a proper dinner without a lot of noise.
Each hotel leans into its own personality: Gladstone for music and neighbourhood energy, Broadview for views and oysters, Postmark for a relaxed rooftop dinner outside the downtown core.
