What's the closest beach to Winchester Inn?

The nearest is Lanikai Beach, about 2481 mi away (straight-line).

What is the cancellation policy at Winchester Inn?

It depends on the rate you pick — many rooms at Winchester Inn offer free cancellation. You'll see each room's exact policy before you book.

Are there extra fees at Winchester Inn?

Any mandatory property fees are shown in your all-in total before you book — no surprises at checkout.

What guest services does Winchester Inn offer?

Winchester Inn offers services such as concierge, laundry, luggage storage.

Is Winchester Inn a good place to stay?

Guests rate it 9.6/10 (Exceptional) across 628 reviews.

How does pricing work at Winchester Inn on travelpluscost?

One honest price: what the hotel charges us plus one small flat fee — the same for everyone, never based on your data. No hidden markup and no fake discounts.

Winchester Inn

Name: Winchester Inn
Address: 35 South 2nd Street, Ashland, US
Rating: 9.6

9.6628 reviews

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Where to?

Hotel

35 South 2nd Street, Ashland

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Top-rated location

Guests rate location 10.0/10.

Guest favorite

Exceptional reviews from recent guests.

Luxury stay

A top-tier 5-star property.

Guests loved it

Charming location

Popular amenities

Free WiFiParkingRestaurantBarAir conditioningLaundryAccessibleFamily rooms

About Winchester Inn

Luxurious Accommodations

Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests.

Gourmet Dining Experience

Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day.

Concierge Service and Convenience

Good to know about Winchester Inn

Check-in

04:00 PM

Check-out

11:00 AM

Pets

Not allowed

Children

Welcome

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Winchester Inn

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How Winchester Inn's price works

One flat fee

The price is what the hotel charges us plus one small, flat service fee — the same for every guest.

No surveillance pricing

We never use your device, location or browsing history to decide what you pay.

All-in, no surprises

Taxes and known fees are shown up front. What you see is what you book.

Winchester Inn reviews

9.6

Exceptional

628 reviews · updated January 2026

Cleanliness8.5

Service10.0

Location10.0

Room Quality9.4

Amenities9.5

Value for Money9.4

Guests loved

+ Charming location
+ Amazing breakfast

Worth noting

– Old building issues
– Staff availability after hours

Things to do near Winchester Inn

35 South 2nd Street, Ashland

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Winchester Inn property amenities

Internet

WiFi available
Free WiFi

Parking & transportation

Parking
Free Parking
Private parking
Accessible parking
Street parking

Food & drink

Restaurant
Bar

Family

Family rooms

Accessibility

Facilities for disabled guests

Things to do

Garden
Golf course
Tennis court

Services & conveniences

Luggage storage
Fax/photocopying
Dry cleaning
Daily housekeeping
Concierge service
Staff adhere to local safety protocols
Laundry washed per local authority guidelines

Climate & comfort

Non-smoking rooms
Air conditioning
Heating
Non-smoking throughout

Hiking
Meeting/banquet facilities
Special diet menus - on request
Allergy-free room
Outdoor furniture
Wine/champagne
Guest rooms disinfected between stays
Cleaning standards that are effective against Coronavirus
Physical distancing rules followed
Hand sanitizer in guest room and key areas
Cashless payment available
Fire extinguishers
Sanitized tableware & silverware
Invoice provided
Guests can opt-out any cleaning services during stay

Winchester Inn room amenities

Bedroom

Wardrobe or closet

Bathroom

Shower
Hair dryer
Bathrobe
Toilet
Private bathroom

Entertainment

TV
Radio
Video

Food & drink

Coffee/tea maker
Minibar
Refrigerator
Electric kettle
Microwave

Internet & phone

Telephone

Comfort

Air conditioning
Fan
Heating

Seating Area
Desk
Fireplace

Frequently asked questions about Winchester Inn

What are the check-in and check-out times at Winchester Inn?

Check-in starts at 04:00 PM and check-out is by 11:00 AM.

Does Winchester Inn have WiFi?

WiFi is available at Winchester Inn. Check your room's details for whether it's free or carries a charge.

Is parking available at Winchester Inn?

Yes, parking is available at Winchester Inn. A fee may apply — see the property's important information.

Does Winchester Inn have a restaurant?

Yes, there is on-site dining at Winchester Inn. There's also a bar or lounge.

Do the rooms at Winchester Inn have air conditioning?

Yes, rooms at Winchester Inn have air conditioning.

Is Winchester Inn wheelchair accessible?

Winchester Inn offers facilities for guests with disabilities. Contact the property to confirm the specifics for your needs.

Is Winchester Inn pet-friendly?

No, pets are not allowed at Winchester Inn.

Is Winchester Inn family-friendly?

Yes, Winchester Inn welcomes families.

Is Winchester Inn non-smoking?

Yes, Winchester Inn is non-smoking throughout.

How far is Winchester Inn from Honolulu airport (HNL)?

It's about 2494 mi (straight-line) from Honolulu airport (HNL).

Winchester Inn policies

Parking

Free private parking is possible on site (reservation is not needed).

Internet

WiFi is available in all areas and is free of charge.

Pets

Pets are not allowed.

Children and extra bed policy

Children of any age are allowed. Children up to and including 2 years old stay for free when using an available cot. Children up to and including 8 years old stay for free when using an existing bed. Children up to and including 8 years old stay for free when using an available extra bed. People 9 years old and over stay for US$45 per person per night when using an available extra bed. Any type of extra bed or child's cot/crib is upon request and needs to be confirmed by management. Supplements are not calculated automatically in the total costs and will have to be paid for separately during your stay.

You need to know about Winchester Inn

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation. A deposit may be required at the property.