Stays in Pickering

Consider the Lilies Bed and Breakfast

Air-conditioned rooms with free breakfast and parking near local nature

Why guests love it

Free breakfast each morning, plus free Wi-Fi and parking, keep a family stay simple at Consider the Lilies Bed and Breakfast, and some rooms have a kitchen for snacks. The house is smoke-free and air-conditioned. Eldred King Woodlands is a short taxi ride away for a walk in the trees, and local dining is close. The airport is a longer commute, so this is a quiet base rather than a transit stop.

The stays

Practical Pickering base with easy airport access and local dining

Why guests love it

Rated 10 from 12 reviews, The Stays works as a no-fuss base where practicalities matter most. Kingston Road at Claremore Avenue, with public transport nearby, is a two-minute walk, and La Scogliera Italian Cuisine, six minutes on foot, gives families an easy dinner without driving. The listing details no kitchen, pool or play area, so I would treat it as a short stay or a stopover: the airport is 48 minutes by taxi or 1 hour 25 minutes by public transport.

Willow Springs Winery

A tranquil winery stay near Pickering, with easy airport access

Why guests love it

I would pick Willow Springs Winery for a calm, vineyard-side stay in Pickering rather than a convenient one. Its 9.6 rating rests on about 780 reviews, which makes it one of the better-reviewed places I compared here. Applewood Farm is a seven-minute taxi ride away, but the airport is 48 minutes by taxi, so I would not choose it for an early flight. A car or taxi is part of the plan.

Tru by Hilton Oshawa

Pet-friendly hotel with free breakfast, Wi-Fi, and a 5-minute walk to the airport

Why guests love it

Tru by Hilton Oshawa keeps a family stay simple: the air-conditioned family rooms are modern, the continental buffet breakfast is included each morning, and parking and WiFi are free. The hotel is pet-friendly, so the dog can come along, and there is a fitness room for parents who want a workout. The front desk is open 24 hours, which helps with late arrivals after a long drive. Guests rate it above 9.

Chalet Claremont Bed and Breakfast

Log-cabin comfort with a pool, near Dagmar Ski Resort

Why guests love it

Dagmar Ski Resort is about a 10-minute taxi ride from Chalet Claremont, so I see this log cabin as a family base for winter weekends. The pool gives children an easy activity on site, and free parking makes arriving by car simple. The property is smoke-free and has Wi-Fi. With the airport a 51-minute taxi ride away, it suits a driving trip better than a flying visit. Its 8.8 score rests on only nine reviews.

Residence & Conference Centre - Oshawa

Budget-friendly suites with kitchenettes near Durham College

Toronto Marriott Markham

Contemporary hotel with an indoor pool, hot tub, and pet-friendly rooms

Why guests love it

Toronto Marriott Markham suits families who want a modern hotel with something for children after a day out: the elevated indoor infinity pool and the hot tub are the evening draw. Rooms have floor-to-ceiling windows and keyless entry, the fitness centre is open 24 hours, and the hotel is pet-friendly. It sits a minute's walk from Enterprise Boulevard and Birchmount Road in downtown Markham, about 34 minutes by taxi from the airport.

Cedar Beach Resort

Lakefront camping with two pools, a beach, and family-friendly amenities

Why guests love it

Cedar Beach Resort is a lakefront campground rather than a hotel, and that is exactly its appeal for families. Children get a beach, two pools, playgrounds and sports facilities in one place, which fills summer days without a single drive. Some accommodations include kitchens, and the property is smoke-free and listed as kid-friendly. Families bring a tent, RV or trailer, so it suits those who enjoy camping. Free parking and Wi-Fi keep the practical side simple.

Hilton Garden Inn Toronto/Ajax

Pet-friendly hotel with indoor pool and hot tub near Lynde Shores

Why guests love it

Hilton Garden Inn Toronto/Ajax is an easy, relaxed choice for families east of Toronto. The indoor pool and hot tub are available whatever the season, the hotel is listed as kid-friendly and accessible, and an on-site restaurant and bar save a drive at dinner. Free parking and free WiFi keep things simple, and pets are welcome. Lynde Shores Conservation Area is a short drive for a nature outing. Over 1,300 reviews give it 8.4/10.

Homewood Suites by Hilton Ajax, Ontario, Canada

All-suite hotel with kitchens, free breakfast, and an indoor pool

Why guests love it

Homewood Suites in Ajax is built for longer family stays: every unit is a suite with a kitchen, so you can cook simple meals instead of eating out three times a day. Breakfast is included, the indoor pool keeps children busy in any season, and pets are accepted. The local conservation areas are within easy reach for a walk. Rooms are described as unfussy, so expect function over style. I would pick it for a week, not a night.

Hilton Toronto/Markham Suites Conference Centre & Spa

All-suite hotel with spa, indoor pool, and pet-friendly options in Markham

Why guests love it

Hilton Toronto/Markham Suites is an all-suite hotel, so families get more room than in a standard double, and some suites include a kitchen. The indoor pool keeps children busy, adults can book the full-service spa, and two restaurants and a lounge are on site. Pets are welcome. Local restaurants are a short walk away, and the airport is about 34 minutes by taxi. With more than 5,400 reviews at 8.4/10, it is a well-tested choice.

Holiday Inn Express Whitby Oshawa by IHG

Modern lodging with a seasonal outdoor pool, hot tub, and free breakfast

Why guests love it

Holiday Inn Express Whitby Oshawa is a straightforward base for a family on the road. The free breakfast bar gets everyone fed before you leave, parking and Wi-Fi are free, and children can use the hot tub and, in summer, the seasonal outdoor pool. Outside the warm months there is no pool, so plan accordingly. Station Gallery is a short taxi ride away. I see it as a sensible stopover rather than a destination in itself.

Cat House

Convenient Pickering stay with airport shuttle and free parking

Why guests love it

The Cat House is a simple, smoke-free stay with air conditioning, free Wi-Fi and free parking, rated 8 from 24 reviews. For families, the airport shuttle is the practical asset: Toronto Pearson is around 40 minutes by taxi, or 1 hour 35 minutes by public transport, which is long with luggage and children. I would book it for a night before or after a flight rather than a holiday, since the listing mentions no pool, kitchen or play area.

Monte Carlo Inn & Suites - Downtown Markham

Indoor saltwater pool and Mediterranean dining in Downtown Markham

Why guests love it

Monte Carlo Inn & Suites Downtown Markham works for families mainly because of its indoor saltwater pool, which gives children something to look forward to after a day out. Breakfast and Wi-Fi are free, the property is smoke-free and kid-friendly, and some suites have an in-room spa bath for parents. The Mediterranean restaurant and wine bar save a drive at dinner, and Highway 404 is close for day trips across the region.

Pickering Casino Resort

A contemporary casino resort with a pool, hot tub, and pet-friendly rooms

Why guests love it

Pickering Casino Resort is built around a casino and its restaurants and cocktail bars, so I see it more as an adults' address than a family one, but there is a pool, a hot tub and a fitness centre for everyone. Rooms come with free WiFi, parking is free, and pets are accepted. Ajax Waterfront Park is close by for an outdoor break. Guests rate it 7.8 from 4,612 reviews.

Delta Hotels Toronto East

Modern rooms with a saltwater pool, hot tub, and pet-friendly policy

Why guests love it

Delta Hotels Toronto East has an atrium with a saltwater indoor pool and a hot tub, the feature I would mention first to families, since it works whatever the weather. The on-site Japanese restaurant offers a change from standard hotel menus, which can please curious young eaters. Rooms are modern and air-conditioned, and pets are welcome. Village Green Square at Metrogate Park is a short walk away, giving children some outdoor space between outings.

Residence Inn by Marriott Whitby

Pet-friendly studios with kitchenettes, an indoor pool, and free breakfast

Why guests love it

I would recommend the Residence Inn Whitby to families planning a longer stay east of Toronto. Studios and suites are colourful, some with kitchenettes, which helps with simple meals. The free hot breakfast covers mornings, and the indoor pool and hot tub give children an evening plan. Parking and Wi-Fi are free, and pets are accepted. Note that the hotel is in Whitby, a short drive east of Pickering.

Best Western Plus Executive Inn

Indoor pool, free breakfast, and parking near Markham Road

Why guests love it

Best Western Plus Executive Inn is a three-star hotel in Pickering that I would recommend to families who want an easy, relaxed stay. The indoor pool, complimentary breakfast and free parking take care of the basics, and public transport connections are a short walk away. Rooms are air-conditioned, and a fitness center and a restaurant are on site. The rating of 7.8 points to a practical stay rather than a polished one.

Lilen's Home

An ideal base for airport access and local transit in Pickering

Why guests love it

A transit stop at St Clair Avenue East and Jeanette Street is a one-minute walk from Lilen's Home, which matters more here than amenities, since the listing names none. The Scarborough Bluffs are a six-minute taxi ride, an easy outing with children, and Toronto Pearson is about 45 minutes by taxi. The 7.6 score rests on only five reviews, so I would book it as a practical stopover rather than a holiday base.

Beautiful Family Home Near a Nordic Spa

A family home in Pickering for spa breaks and airport access

Quality Suites Whitby

Pet-friendly all-suite lodging with free breakfast and fitness center

Why guests love it

Quality Suites Whitby gives a family more space than a single hotel room, since every unit is a suite. The hot breakfast is free, as are parking and Wi-Fi, and the full-service laundry is handy after a few days on the road. Pets are accepted. There is a fitness centre but no pool listed, so children will need their fun elsewhere. The guest score of 7.4 is middling, so I would treat it as a practical base.