When to book
Tips & FAQs
Nearby stays
Winchester Inn
3 stars

Winchester Inn

35 South 2nd Street, Ashland, OR 97520, United States
+1 541 488 1113

rate per night


based on 348 reviews

Winchester Inn
Sat 13.04
Wed 17.04
Room type
Nightly total
Double room
Standard room
Queen room

About Winchester Inn

  • Inn Room
    Room at a smaller hotel or guest house
  • Freebies
    This stay includes Wi-Fi, Breakfast, and Parking for free

Situated near the area's tourist attractions, Winchester Inn is moments from Lithia Park. Only a short walk from IOOF Building, it offers comfortable rooms equipped with a refrigerator, tea and coffee making facilities and a mini bar.

The bed & breakfast provides comfortable accommodation, in addition to a concierge, free Wi-Fi and luggage storage. In fine weather, an outdoor terrace offers a nice spot to relax.

Winchester Inn has 24 rooms offering all the essentials to ensure a comfortable stay. They are also fitted with a CD player, a dishwasher and a microwave.

Winchester Inn is just a short stroll from Ashland Masonic Lodge Building. Lithia Springs Hotel is under a two-minute walk from the bed & breakfast.

Photos of Winchester Inn

Latest deals for Winchester Inn

Sat 13.04
Wed 17.04
Double room
1 queen bed
1 queen bed
1 queen bed
King room
bed type unknown
bed type unknown
bed type unknown
Queen room
bed type unknown
bed type unknown
bed type unknown
Deluxe room
bed type unknown
Standard room
bed type unknown
bed type unknown
bed type unknown

*Total includes estimated local taxes & fees payable on check out.

Prices are based on 1 night including VAT, excluding local taxes and fees.

Amenities at Winchester Inn

  • Tennis
  • Free Wi-Fi
  • Private bathroom
  • Complimentary breakfast
  • Coffee machine
  • Terrace/Patio
  • Balcony
  • Air-conditioned
  • Flat-screen TV
  • TV


  • Wi-Fi available in all areas
  • Internet
  • Fan
  • Fire extinguisher
  • Free toiletries
  • Smoke alarms
  • Heating
  • Air-conditioned
  • Free Wi-Fi
  • Linens
  • Towels
  • Shampoo
  • Body soap
  • Trash cans
  • Conditioner


  • Family rooms
  • Garden view
  • Hardwood or parquet floors
  • Inner courtyard view
  • Mountain view
  • Storage available
  • Quiet street view
  • Fireplace
  • Seating area
  • Sofa
  • Telephone
  • Carpeted
  • City view

Accessibility and suitability

  • Entire unit located on ground floor
  • Entire unit wheelchair accessible
  • Hypoallergenic
  • Hypoallergenic pillow
  • No smoking
  • Non-feather pillow
  • Private entrance
  • Increased accessibility
  • Roll-in shower
  • Allergy-free room
  • Toilet with grab rails
  • Upper floors accessible by stairs


  • Hairdryer
  • Bathrobe
  • Private bathroom
  • Shower
  • Shower cap
  • Additional bathroom
  • Bathtub
  • Spa bath
  • Toilet
  • Toilet paper
  • Toothbrush
  • Walk-in shower


  • Wine glasses
  • Electric kettle
  • Special diet menus (on request)
  • Restaurant
  • Bar/Lounge
  • Food can be delivered to guest accommodation
  • Minibar
  • Microwave
  • Tea/coffee maker
  • Refrigerator
  • Coffee machine


  • Extra-long beds (> 2 meters)
  • Feather pillow
  • Fold-up bed
  • Socket near the bed
  • Alarm clock
  • Sofa bed
  • Clothes rack
  • Wardrobe or closet

Services and conveniences

  • Wake-up service
  • Concierge service
  • Meeting/Banquet facilities
  • Room service
  • Key access
  • Bottle of water

Media and entertainment

  • Flat-screen TV
  • Cable or satellite TV
  • Radio
  • TV
  • Smartphone dock


  • Outdoor furniture
  • Garden
  • Terrace/Patio
  • Balcony

Things to do

  • Gift shop
  • Golf
  • Hiking

Parking and transportation

  • Free parking
  • Private parking


  • Laundry service
  • Iron and ironing board


  • Fax/photocopying
  • Desk

Health and safety

  • Daily housekeeping

Family friendly

  • Complimentary breakfast


  • Tennis

Reviews of Winchester Inn

All reviews are collected from real users with a verified booking made with KAYAK or one of our trusted external partners.

WonderfulBased on 348 verified guest reviews

No reviews found. Try removing a filter, changing your search, or clear all to view reviews.


35 South 2nd Street, Ashland, OR 97520

What's nearby

  • Oregon Cabaret Theatre78 m
  • Waterstone Spa110 m
  • Lithia Springs Hotel135 m
  • Ashland Library203 m
  • New Theater236 m
  • Angus Bowmer Theater258 m
  • Elizabethan Stage - Allen Pavilion258 m
  • Oregon Shakespeare Festival292 m
  • IOOF Building0.4 km
  • Lithia Park0.7 km
  • ScienceWorks Hands-On Museum1.9 km
  • Schneider Museum of Art1.9 km



Check in anytime after 16:00, check out anytime before 11:00


Cancellation/prepayment policies vary by room type and provider.

When to book a room at Winchester Inn

Price per night. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

FAQs when booking at Winchester Inn

  • Where is Winchester Inn located?

    Winchester Inn is located at 35 South 2nd Street, 0.2 km from the center of Ashland. Oregon Cabaret Theatre is the closest landmark to Winchester Inn.

  • When is check-in time and check-out time at Winchester Inn?

    Check-in time is 16:00 and check-out time is 11:00 at Winchester Inn.

  • Does Winchester Inn offer free Wi-Fi?

    Yes, Winchester Inn offers free Wi-Fi.

  • Does Winchester Inn offer free parking?

    Yes, Winchester Inn offers free parking.

  • How far is Winchester Inn from the airport?

    Winchester Inn is 23.8 km from Medford. Winchester Inn is 79.5 km from Klamath Falls Kingsley Field.

  • How does KAYAK find such great Winchester Inn hotel deals?

    KAYAK scours the web for all room deals available at Winchester Inn in Ashland and lets you compare them to find the best rate for your stay. Many different travel sites will offer discounts or deals at different times for rooms at Winchester Inn and KAYAK will provide you with prices from a huge range of travel sites. That means that you can always find a great deal for Winchester Inn.

Nearby hotels and places to stay

Courtside Cottage - Walkscore 93 - Dog Friendly0.05 kmBalcony, air-conditioned, Coffee machine₪911+
1907 Charmer, Perfect Downtown Location, So Clean!0.07 km₪1,300+
2-star hotel
49% cheaperColumbia Hotel0.08 km₪466+
3-star hotel
26% cheaperAshland Springs Hotel8.6 Excellent (392 reviews)0.14 kmSpa and wellness center, Fitness center, Restaurant₪671+
78% cheaperOne Block To Theater, Park And Town -- Walk Everywhere!0.47 kmKitchen, Tennis, terrace/patio₪199+
72% cheaperAvailable October 12-January 30th. Spacious Historic House one block to Town!0.37 km₪251+
67% cheaperAdjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 30.46 kmAir-conditioned, Coffee machine₪296+
64% cheaperAdjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 20.58 kmAir-conditioned, Coffee machine₪326+
Swank House on Main St in Ashland10 Excellent (3 reviews)0.35 kmKitchen, air-conditioned, Washing machine₪1,409+
30% cheaperHanna's House by WanderLodges10 Excellent (8 reviews)0.26 kmAdults only, Kitchen, terrace/patio₪637+
26% cheaperCharming Space Next to Everything, Walk Anywhere!10 Excellent (12 reviews)0.43 kmAdults only, Kitchen, wifi₪667+
Quiet and peaceful cottage close to downtown9.4 Excellent (19 reviews)0.8 kmKitchen, wifi, terrace/patio₪1,233+

Good to know

Value for money


Distance to city center

0.2 km

Nearest Airport


Distance to airport

23.5 km