TOP Luxury Hotels in Southern Oregon for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

A town nestled in a valley with a prominent building in the foreground and hills in the background.

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Check availability on Southern Oregon Luxury Hotels

Tonight

15 Sept - 16 Sept

Tomorrow

16 Sept - 17 Sept

This weekend

18 Sept - 20 Sept

Next weekend

25 Sept - 27 Sept

Our top choices for Southern Oregon luxury hotels

A Victorian-style building with ornate architectural details, large windows, and a red door.

A room with a bay window, two upholstered chairs, a round ottoman, and a small wooden table.

A room with a glass display case containing wine bottles and glasses, a white chair, and a large window with curtains.

A patio area with string lights, potted plants, and a stone pathway.

1. McCall House Boutique Inn

Historic Downtown District

S$390

includes taxes & fees

20 Sept - 21 Sept

A spacious indoor seating area with blue sofas and round tables, large windows with a view of the beach and umbrellas, and a flat-screen TV mounted on the wall.

A deck with outdoor seating, a bar area, and a fire feature.

A hotel lobby with a wooden reception desk, a large chandelier, and a compass-themed floor design.

A hotel room with two beds, a desk, a TV, and a window with a view of the mountains.

2. Compass by Margaritaville in Medford

Medford

S$233

includes taxes & fees

12 Oct - 13 Oct

A large, white, multi-story house with a stone foundation, multiple chimneys, and a well-maintained lawn.

A bar area with a polished wooden counter, a tap with a handle, and a glass rack above.

A stone staircase leading up to a white building with a bell tower, surrounded by greenery and a view of hills.

A spacious living room with leather sofas, a fireplace, and wooden beams on the ceiling.

3. Hummingbird Estate Wine & Suites

Central Point

Savour champagne service and vineyard views at this luxurious wine estate bed & breakfast offering tranquil luxury in rural Oregon.

S$192

includes taxes & fees

22 Sept - 23 Sept

A garden pathway with wisteria and red flowers, surrounded by lush greenery.

A rustic building with a porch, surrounded by lush greenery and a sign indicating it is a forest.

A bedroom with a bed, a nightstand, a lamp, a chair, a potted plant, and a door.

A cozy library with bookshelves, a fireplace, and comfortable seating.

4. Arden Forest Inn

Ashland

S$287

includes taxes & fees

14 Oct - 15 Oct

A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

A rustic wooden barn with a sloped roof, surrounded by a field of white daisies.

A garden with a pond, stone walls, and various plants.

A gazebo with a wooden roof and white curtains, surrounded by lush greenery and autumn-colored trees.

5. Country Willows Inn and Estate

Ashland

S$327

includes taxes & fees

16 Sept - 17 Sept

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

A compact kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs, and a small seating area with a blue chair and a table.

A compact kitchen with white cabinets, a dining table with chairs, a refrigerator, and a built-in oven.

A single-story house with a covered porch, a small garden with rocks and a tree, and a mailbox.

6. Hanna's House by WanderLodges

Historic Railroad District

S$419

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

A bedroom with a bed, a wooden floor, a patterned rug, a sofa, and a wardrobe.

A modern kitchen with blue cabinets, stainless steel appliances, a built-in oven, and a microwave.

A wooden staircase leading to a kitchen with a central island and bar stools.

7. The Mountain Ave House by WanderLodges

Ashland

S$506

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

A kitchen with white cabinets, a microwave, and a window with curtains.

A living room with a glass coffee table, a television, a chair, and a view of mountains through the window.

A two-story house with a prominent staircase leading to the entrance.

8. Barclay Klum House by WanderLodges

Ashland

S$376

includes taxes & fees

27 Sept - 28 Sept

View all properties

Top Southern Oregon Hotel Reviews

Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport

8/10 Good

"The whole place was on the run down side of things, but the staff was great. The breakfast was not good. We would stay there again."

Best Western Crater Lake Highway White City/Medford

Best Western Crater Lake Highway White City/Medford

10/10 Excellent

"Look like new"

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent

"The cafe was understaffed. Otherwise, another amazing stay."

Days Inn by Wyndham Klamath Falls

Days Inn by Wyndham Klamath Falls

10/10 Excellent

"Thumbs up for a big box truck"

Ramada by Wyndham Medford Airport North

Ramada by Wyndham Medford Airport North

10/10 Excellent

"The room was nice clean but small"

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent

"This is always a go to when we travel for the Shakespeare festival - the pool is 24hrs so it’s great for traveling with older kids."

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