Winchester Inn

Top rated by guests

9.4Outstanding

(415 Ratings)

"Gorgeous and well maintained"

Verified guest

Don't miss out! Price and availability may change

9.4 / 10

Outstanding(415 Ratings)

Hotel in Ashland, OR

5-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this hotel

Historic Charm

Amenities

Business facilities

Golf course (within 2 mi)

Concierge services

Free WiFi/internet

Free Parking

Air conditioning

Non-smoking

Heating

Wheelchair accessible

Bar

WiFi/Internet

Garden

Laundry services

Accessible Parking

Family friendly

Key access

Housekeeping available

Fire alarm

Fire extinguisher

Tennis court

Cleaning products

Map of Ashland, OR

Nearby attractions

Rogue Valley ZipLine Adventure

23 mi

Crater Rock Museum

17.3 mi

Cascade-Siskiyou National Monument

15.8 mi

Escape Ashland - "The Scottish Play"

0.2 mi

Available Rooms

Ratings and reviews

9.4 / 10

Outstanding(415 Ratings)

100% verified reviews

10 / 10Outstanding·Sep 2026

Gorgeous and well maintained

10 / 10Outstanding·Sep 2026

The room and property were charming and comfortable. We enjoyed the breakfast and had one meal at Alchemy, which was also very good.

Everything was great. Parking, I guess, was a little tight, but provided and convenient. The television in the room was pretty small.

8 / 10Excellent·Aug 2026

Great location. Lovely little place. Our room was nice. Breakfast was included & you could choose from a menu!

10 / 10Outstanding·Aug 2026

Everything about the property--and I mean everything!--was top notch and exceptional: the welcome, the room, breakfast, housekeeping, historic architecture, landscaping, location. We love the place and will make it part of our twice annual trip through Ashland.

N/a

$$$$

FAQs

Is parking included with this hotel?

Parking is not specified as an available amenity at Winchester Inn. For more information, we encourage you to contact the property about where to park.

Is there a pool at this hotel?

We didn’t find pool listed as an amenity for this hotel. It may be worth double checking if a pool is important for your stay.

Is Winchester Inn pet friendly?

Unfortunately, this hotel is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Winchester Inn?

We found 21 amenities for this rental. This includes business facilities, golf course (within 2 mi), concierge services, free wifi/internet, and free parking.

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