The Best Places to Book Your Stay Near Mount Ashland, Oregon

Whether you’re dining under the stars on wooden decking or snuggling up by a wood fire, rustic charm is the vibe at this pine-enveloped lodge. Just 10mi (16km) – or a 15-minute drive – from Mount Ashland, Callahan’s is also close to Lake Emigrant National Park and southern Oregon’s clutch of fine wineries. The premium and luxury suites are particularly good for hikers or skiers – and they come with jacuzzis, so you can soothe tired legs at the end of the day.

The name of this Ashland B&B sounds like something out of a romantic novel – and the location could well be in one, too. Five rolling acres of land (2ha) – with gardens, ponds and a heated swimming pool – provide a gorgeous and well-maintained backdrop to your stay. The inn building is a stunner too, complete with wraparound porches and nine immaculate rooms. If you want a truly romantic experience, opt for one of the suites – featuring wood burners, private patios and jacuzzis.

This bed and breakfast in Ashland – around half an hour’s drive from the ski resort – is a particularly good find for cyclists. You can fully revamp your bike while here with the free cleaning and repair kit, or leave them in the secure lock-up before hitting one of the local trails. Foodies will also be delighted with the multi-course breakfast here – including home-baked goodies and fresh quiches – served on a deck outside under an oak tree when the weather allows.

Every attention has been paid to comfort at downtown Palm Cottages. Each of its 16 rooms, suites and studios have king and queen beds, flat-screen TVs and pillow menus – while several have fireplaces for the colder months. The best perk is the surrounding garden: with its curvaceous salt-water pool surrounded by day beds, a picnic area and lush planting.

A classic and cozy choice, Ashland Flagship Inn is more spacious than a boutique hotel but friendlier than a high-rise chain. The location – on Siskiyou Blvd right next to the South Oregon University – is great for those wanting to access all the sights and local culture of the city, as well as the mountains beyond. The rooms are furnished in florals and checks – homely without going overboard on chintz – and the outdoor pool feels like a real perk for such a central location.

There’s a relaxed, retro vibe to this hotel in the northern, hilly part of Ashland – with the trademark splashes of peppy orange in the decor and diner-esque restaurant, Luna. It’s a top choice for skiers, running a free ski shuttle to Mount Ashland Ski Area during the winter months. In the summer, active guests can make the most of the hotel’s outdoor tennis courts, fitness center, free bike hire, pool and hot tub.

It’s not surprising that this Ashland mansion feels a cut above. Built by gold-prospector-turned-Ashland-Mayor John McCall in 1883, the house became an upper-crust guesthouse back in 1981. Today, it’s an impeccable blend of period antiques, signature bathroom amenities and gourmet two-course breakfasts. Optional in-room massages and freshly baked cookies every afternoon are just a couple of the touches that continue to put McCall House in a class of its own.

This many-gabled inn and its several annexes offer a wide range of options to its guests. Choose from simple rooms, suites – many with jacuzzis – and even standalone cottages, if you want something a little more independent. All accommodation options offer a complimentary breakfast, with the option to dine in the award-winning Alchemy Restaurant and Bar. Winchester Inn is also close to shops, galleries and the Oregon Shakespeare Festival – all in downtown Ashland.

Deep in the countryside – on the edge of the Hyatt reservoir – this cabin really helps you and your family feel away from it all. Aside from the outdoor adventures on your doorstep, you can revel in all the rustic home comforts that this woodland lodge provides. In winter, it’s all about family meals at the dining table, warmed by the wood-burning stove. Come summertime, while away long evenings out on the porch, playing one of the supplied board games. All year-round, it’s a cozy, rustic place to spend your holiday time.

Just a 20-minute drive from Mount Ashland ski resort, this spacious, three-bedroom cabin has incredible views across the Siskiyou mountains. There’s a reason this place is called Sunset as when dusk falls, there’s no escaping the full glory of the sun’s last rays – whether you’re barbecuing out on the decking or sitting in the glow of the picture windows of the plush living room.