The Best Hotels with Bars in Ashland, OR from NT$2,792 in 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ashland hotels with a bar

A grand lobby with a high ceiling, large windows, and a central staircase.

1. Ashland Springs Hotel

Historic Downtown District

Tamara

NT$3,938 total

includes taxes & fees

Dec 1 - Dec 2

2. Callahan's Mountain Lodge

Ashland

Cameron

NT$3,461 total

includes taxes & fees

Dec 11 - Dec 12

A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

3. Ashland Hills Hotel & Suites

Ashland

Nicholas

NT$3,918 total

includes taxes & fees

Nov 11 - Nov 12

A large, two-story house with a wrap-around porch and a steeply pitched roof.

4. Winchester Inn

Historic Downtown District

Ellen

NT$5,412 total

includes taxes & fees

Nov 30 - Dec 1

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.

5. Compass by Margaritaville in Medford

Medford

Sharon

NT$5,899 total

includes taxes & fees

Dec 8 - Dec 9

A spa area with a hot tub, seating, and large windows offering views of buildings and a distant landscape.

6. Hilton Garden Inn Medford, OR

Medford

Steven

NT$3,141 total

includes taxes & fees

Dec 6 - Dec 7

A Courtyard hotel with a covered entrance, a van, and a parking lot.

7. Courtyard by Marriott Medford Airport

Medford

james

NT$4,072 total

includes taxes & fees

Nov 29 - Nov 30

A modern two-story house with a wooden exterior and stone accents, surrounded by landscaped gardens with various plants and a flagpole.

8. Resort at Eagle Point

Eagle Point

Kynta

NT$5,731 total

includes taxes & fees

Nov 14 - Nov 15

A hotel with a prominent Red Lion sign, a covered outdoor seating area, and a building with a green awning.

9. Red Lion Hotel Rogue Regency Medford Airport

Medford

Katelyn

NT$3,468 total

includes taxes & fees

Nov 13 - Nov 14

A modern hotel lobby with multiple seating areas, including round tables and chairs, and a bar area with stools.

10. Springhill Suites By Marriott Medford Airport

Medford

Rijab

NT$4,363 total

includes taxes & fees

Dec 7 - Dec 8

View all properties

Top Ashland Hotel Reviews

Compass by Margaritaville in Medford

Medford

10/10 Excellent

Stephanie

Winchester Inn

Historic Downtown District

10/10 Excellent

This hotel is comprised of two Victorian style houses. One is just rooms and the other is the restaurant/bar with rooms too (I think). The gardens were gorgeous, the staff was super friendly and here was the clincher...they could feed my wife despite several food allergies. We were so floored when we came down to breakfast and they had made my wife a special pastry and seamlessly provided her second course. The rooms are in keeping with the style of the property. If you want sleek...

Anonymous traveler

Springhill Suites By Marriott Medford Airport

Medford

10/10 Excellent

Theresa

Ashland Springs Hotel

Historic Downtown District

10/10 Excellent

Jay

Ashland Hills Hotel & Suites

Ashland

10/10 Excellent

Melissa

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

Hummingbird Estate Wine & Suites

Central Point

10/10 Excellent

I can highly recommend Hummingbird!!! My recent stay was excellent, on every level! The property is gorgeous, the suites are clean, modernized but still have been decorated to go with their signature style, the service was impeccable and the breakfasts were delicious! Every morning something new, fresh, and a culinary delight! Thank you so all at Hummingbird for a wonderful stay! I was staying as a solo for this trip, but would love to return again with my Hubby! I would absolutely stay again...

Anonymous traveler

Resort at Eagle Point

Eagle Point

10/10 Excellent

Anonymous traveler

Courtyard by Marriott Medford Airport

Medford

10/10 Excellent

Donald

Hilton Garden Inn Medford, OR

Medford

10/10 Excellent

Sarah

Red Lion Hotel Rogue Regency Medford Airport

Medford

10/10 Excellent

Cheyenne

Frequently Asked Questions

Searching for hotels with bars in Ashland?

If you'd like a place to stay where you can enjoy an evening cocktail after a day out and about, Ashland offers 303 hotels and other lodging options, including 5 accommodations with an onsite bar. While you're here, consider a visit to Allen Elizabethan Theatre and Angus Bowmer Theatre.

What are the best hotels with bars in Ashland?

Here are some of the top Ashland hotels with bars: Ashland Hills Hotel & Suites: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Callahan's Mountain Lodge: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Ashland Springs Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Winchester Inn: Inn with restaurant. Enjoy the bar, free breakfast, and free WiFi. Bayberry Inn and Retreat: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.

How many hotels with onsite bars will I be able to find in Ashland?

Expedia has 5 hotels with a bar in Ashland.

What is there to do in Ashland?

If you have time to explore, consider visiting Allen Elizabethan Theatre, Angus Bowmer Theatre, and Oregon Shakespeare Festival, and then find a cozy spot for a nightcap. Other places to see include Oregon Cabaret Theatre and Lithia Park. Ashland is recognized for its acclaimed theater scene, lively festivals, and top-notch restaurants.

When is the best time to visit Ashland?

Visiting local bars in Ashland is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide the best time for bar hopping. The hottest months are usually August and July with an average temp of 65°F, while the coldest months are December and January with an average of 37°F. Average annual precipitation for Ashland is 33 inches.

How can I get to Ashland and around the area?

You might want to make the most of these transportation options in and around Ashland: Fly into Rogue Valley Intl. Airport (MFR), which is located 14.4 mi (23.3 km) away from the city center. Otherwise, look for flights into Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Find Hotels with Bars in Ashland, OR

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland hotels with a bar

1. Ashland Springs Hotel

2. Callahan's Mountain Lodge

3. Ashland Hills Hotel & Suites

4. Winchester Inn

5. Compass by Margaritaville in Medford

6. Hilton Garden Inn Medford, OR

7. Courtyard by Marriott Medford Airport

8. Resort at Eagle Point

9. Red Lion Hotel Rogue Regency Medford Airport

10. Springhill Suites By Marriott Medford Airport

Top Ashland Hotel Reviews

Compass by Margaritaville in Medford

10/10 Excellent

Frequently Asked Questions

Searching for hotels with bars in Ashland?

What are the best hotels with bars in Ashland?

How many hotels with onsite bars will I be able to find in Ashland?

What is there to do in Ashland?

When is the best time to visit Ashland?

How can I get to Ashland and around the area?

Explore a world of travel with Expedia