Winchester Inn

Suite, 2 Bedrooms (Duet Suite) | Living area | Flat-screen TV

Suite, 1 Queen Bed with Sofa bed (Belvedere) | Living area | Flat-screen TV

Suite, 1 Bedroom (Silverdale) | Living area | Flat-screen TV

Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

9.6 / 10.0

Outstanding(225 Ratings)

Inn in Ashland, OR

1 queen bed

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsGarden, Air conditioner, Internet / Wifi and more

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

About this inn

Victorian Ashland inn in Historic Downtown District with free breakfast
Along with a restaurant, this smoke-free inn has a bar/lounge and a meeting room. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, concierge services, dry cleaning, and free newspapers are onsite.
Winchester Inn offers 21 air-conditioned accommodations with minibars and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Amenities

Air conditioner

Internet / Wifi

Parking

Laundry

Balcony or Patio

Garden

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

Double Room, 1 Bedroom (Garden)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Bedroom (Sylvan)

1 Queen • 1 Sofa • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room (Queen Anne)

1 Queen • 1 Single • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Queen Bed (Patio)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Queen Bed (Marjorie Roy)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

$$$$

Winchester Inn

$$$$

9.6 / 10.0

Outstanding(225 Ratings)

Inn in Ashland, OR

1 queen bed

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsGarden, Air conditioner, Internet / Wifi and more

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

About this inn

Amenities

Air conditioner

Internet / Wifi

Parking

Laundry

Balcony or Patio

Garden

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

Double Room, 1 Bedroom (Garden)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Bedroom (Sylvan)

1 Queen • 1 Sofa • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room (Queen Anne)

1 Queen • 1 Single • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Queen Bed (Patio)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Double Room, 1 Queen Bed (Marjorie Roy)

1 Queen • 350 ft²

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Ratings and reviews

9.6 / 10.0

Outstanding(225 Ratings)

10.0 / 10.0

Aug 2024

Always a great stop on our travels north and south. Great location. Great restaurant. Rooms are great. Staff are very accommodating, highly recommend

10.0 / 10.0

Aug 2024

Loved the luxurious bedding and sweet delivered to the room daily

10.0 / 10.0

Aug 2024

Beautiful, extremely well maintained property in the heart of Ashland with lots of character and deluxe amenities. Very friendly and helpful staff. Gourmet restaurant on premises and superb breakfast with many options. Walk to everything. Highly recommend.

10.0 / 10.0

Jul 2024

Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend.

5.0 / 10.0

Jul 2024

Room very nice. Great location. Delicious food.

10.0 / 10.0

Jul 2024

Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants!

10.0 / 10.0

Jun 2024

Absolutely wonderful property and outstanding service.

10.0 / 10.0

Jun 2024

The staff was courteous, helpful, and conversational. Rooms were clean and stylish.

8.0 / 10.0

Jun 2024

The food is amazing! Unfortunately, there are many things that should be fixed or upgraded. For the price, it should be in perfect condition.

5.0 / 10.0

Jun 2024

Staying at the Winchester Inn is simply stellar beyond compare and it's very convenient to Ashland and walking to the plays.

5.0 / 10.0

Jun 2024

it was cozy and perfect

10.0 / 10.0

Jun 2024

The Winchester is idealic. Its so quaint and pretty. They thought of every detail down to a personal greeting in the room and reservations for their complimentary breakfast, which was like eating at a high end restaurant, and the bed is made by the time you return. The room was so clean, and the towels and bedding were really high quality. And the staff were fantastic! I really look forward to staying here again

10.0 / 10.0

Jun 2024

This was a lovely stopover in Ashland on our way to Santa Barbara. It is a charming, well run inn. This was Memorial Day weekend so breakfast was not “full service” but what we had was delicious.

4.0 / 10.0

May 2024

I booked the Garden Room for a Queen bed and a sofa bed. I even asked again when I was shown the room if the sofa made into a bed and ahead of time asked to be sure there would be extra bedding for the sofa bed. I was assured upon check in that the sofa made into a bed. It does not. The Queen is more of a double than a Queen and the other guest had to sleep in the bay window minus extra bedding. I tried to get help by calling front desk, no answer. The dishwasher offered his condolences, the staff are nice, but this is poor service to not be able to reach anyone for help in the evening. Very disappointed.

10.0 / 10.0

May 2024

The service was delightful

8.0 / 10.0

May 2024

A good place to stay. They need to work on some maintenance issues, though. The included breakfasts are magnificent!

10.0 / 10.0

Apr 2024

We loved everything about this inn!

4.0 / 10.0

Mar 2024

Nice place, amazing food and customer service

10.0 / 10.0

Jan 2024

The room looks very nice. The hotel is in downtown, within walking distance to a few dinning options. It is very continent. The staff is nice. We’d love to stay again!

5.0 / 10.0

Dec 2023

Amazing room with a balcony, fire place, comfy bed and beautiful walk in shower. It was so nice having a beautiful restaurant down stairs.

10.0 / 10.0

Dec 2023

Breakfast was amazing!

5.0 / 10.0

Nov 2023

I came here on a solo vacation and everyone was absolutely amazing the entire time I was there! The inn itself was absolutely beautiful and the food was so delicious!! I will definitely be back!!

10.0 / 10.0

Nov 2023

Beautiful place to stay

10.0 / 10.0

Nov 2023

Located very close to downtown Ashland. Comfortableand clean rooms. All instructions for guests are clearly provided in a series of messages throughout the room and bathroom. The staff is very friendly, and the breakfast is plentiful, varied, and delicious. Choose it if you would like to know the city on foot.

10.0 / 10.0

Oct 2023

The thing that won me over the most was their attention to detail. While the property wasn’t overly “luxurious”, the personal touches made us feel special. We would love to stay here again in the future!

5.0 / 10.0

Oct 2023

This is an excellent hotel. Large room, immaculate furnishings (room cookies too!) and excellent breakfast, plus it is perfectly located to stroll Ashland. Highly recommended.

10.0 / 10.0

Oct 2023

Excellent satff that made our stay a pleasure.

10.0 / 10.0

Oct 2023

This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.

4.0 / 10.0

Sep 2023

We were in the Catherine M room. There was nowhere to plug in the tea or coffee pot. The cords were too short to reach the plugs. The bed was difficult, as it humped up in the middle, and it caused us to feel as if we were falling out the sides. The hostess was very pleasant. Breakfast was good.

10.0 / 10.0

Sep 2023

Staff very nice. Professional. Bed and Breakfast very clean, comfortable and quiet. Little chocolates are not very good. Could change that feature to be a more pleasant, appealing .

5.0 / 10.0

Aug 2023

I was attending a show at the Oregon Shakespeare Festival with my husband and we only stayed one night. Its a 2 min walk to the venue. We were in the heart of downtown, close to restaurants and shops. Our room was pleasantly comfortable, bathroom is spacious and well stocked. The complimentary breakfast was fantastic. We would definitely recommend to our friends and stay here again the next time we pass through.

10.0 / 10.0

Aug 2023

My husband and I had a wonderful weekend in Ashland at the Winchester Inn. Such a unique property and so quiet at night! We stayed in the Sunset room, which has a nice little balcony and great view. The bed was really comfortable and the room was tastefully decorated and very clean. Little touches like a personalized card welcoming us and treats in the room go a long way. Breakfast was amazing...2 course on their beautiful patio. I was very impressed and will definitely be back!

8.0 / 10.0

Aug 2023

Very unique property in that you feel like you are staying at your Grandmother's home. Seemed a bit creepy at first but, the owners warmed up to me after more interactions. I'm not a B&B type as I really don't want everyone to know my business. Neighborhood is experiencing changes and upgrades for the better, but there are still dilapidated houses here and there.

10.0 / 10.0

Jul 2023

Beautiful property in downtown Ashland. Walkable to the theater restaurants shops. The staff was very friendly and welcoming. They called me to let me know early check-in was available.

10.0 / 10.0

Jun 2023

This is a Victorian Inn just a few steps off of Main Street in Ashland. The location is great and the staff is very friendly. I stayed in the Robert Gordon room, which is one bedroom with a living room and bath. I plan to stay here again the next time I am in Ashland.

10.0 / 10.0

Jun 2023

What a beautiful gem! Amazing staff, gorgeous room, delicious food, and a block from the Shakespeare Festival. Can’t wait to come back again.

10.0 / 10.0

Jun 2023

We stayed there for our 53rd Wedding Anniversary. This has to be one of the finest establishments we have ever stayed in. The staff was excellent, the room was outstanding and we will be returning for another stay.

10.0 / 10.0

May 2023

What a grand lady this beautiful Victorian is! Matched with tasteful decor, stellar service, and excellent food and drink! We will definitely be back!

10.0 / 10.0

May 2023

The reception staff were very welcoming, friendly and helpful.

10.0 / 10.0

May 2023

Beautiful location, friendly staff, amazing stay!

FAQs

How much does this inn cost compared to others in Ashland?

The average price for a rental in Ashland is $161 per night. This rental is $29 less expensive than the average.

Is parking included with this inn?

Yes, parking is listed as an amenity at Winchester Inn. For more information, we encourage you to contact the property about where to park.

Is there a pool at this inn?

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

Is Winchester Inn pet friendly?

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

What amenities are available at Winchester Inn?

We found 7 amenities for this rental. This includes air conditioner, internet / wifi, parking, laundry, and balcony or patio.

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Winchester Inn

Inn in Ashland, OR

Reasons to book

About this inn

Amenities

Map of Ashland, OR

Nearby attractions

Available Rooms

Double Room, 1 Bedroom (Garden)

Double Room, 1 Bedroom (Sylvan)

Double Room (Queen Anne)

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Marjorie Roy)

Winchester Inn

Inn in Ashland, OR

Reasons to book

About this inn

Amenities

Map of Ashland, OR

Nearby attractions

Available Rooms

Double Room, 1 Bedroom (Garden)

Double Room, 1 Bedroom (Sylvan)

Double Room (Queen Anne)

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Marjorie Roy)

Ratings and reviews

FAQs

How much does this inn cost compared to others in Ashland?

Is parking included with this inn?

Is there a pool at this inn?

Is Winchester Inn pet friendly?

What amenities are available at Winchester Inn?

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