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Winchester Inn

Rental with Tennis

3 stars

35 South 2nd Street, Ashland, OR 97520

+1 541 488 1113
9.5
Wonderful

based on 437 reviews

$146
Rate

per night

Room type
Provider
Nightly total
Double room
$146
Standard room
$161
King room
$205
25 more Winchester Inn deals
25 more Winchester Inn deals

About Winchester Inn, Ashland

Cleanliness
9.7
Comfort
9.6
Location
9.9
Services
9.5
Staff
9.8
Value for money
9.2
Winchester Inn is situated in Ashland and is close to local landmarks, such as Lithia Park. It is also a short walk from IOOF Building and Ashland Masonic Lodge Building, and is close to many of the area's popular attractions. 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. The rooms offer tea and coffee making facilities, a mini bar and a refrigerator. Bathrobes are also available for extra comfort. The area surrounding Winchester Inn has a range of cafés and restaurants. It is just two minute's walk from Lithia Springs Hotel.

Winchester Inn photos

Winchester Inn room price & deals

jue. 7/17
vie. 7/18
Queen room
bed type unknown
$259
bed type unknown
$267
1 queen bed
$440
Standard room
bed type unknown
$161
bed type unknown
$256
bed type unknown
$262
Deluxe room
bed type unknown
$442
bed type unknown
$564
Double room
1 queen bed
$146
bed type unknown
$255
1 queen bed
$283
Superior room
bed type unknown
$711
bed type unknown
$711
King room
bed type unknown
$205
bed type unknown
$205
1 king bed
$300
*Total includes estimated local taxes & fees payable on check out.
Prices are based on 1 night, including fees but not including taxes.

Inn Amenities & Facilities

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

Basics

  • 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

General

  • 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

Bathroom

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

Dining

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

Bedroom

  • 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

  • Outdoor furniture
  • Garden
  • Terrace/Patio
  • Balcony

Things to do

  • Gift shop
  • Golf
  • Hiking

Parking and transportation

  • Free parking
  • Private parking

Laundry

  • Laundry service
  • Iron and ironing board

Workspace

  • Fax/photocopying
  • Desk

Family friendly

  • Cribs available
  • Complimentary breakfast

Health and safety

  • Daily housekeeping

Fitness

  • Tennis

Winchester Inn Reviews

9.5
WonderfulBased on 437 verified guest reviews
Pros +
  • A great place to stay. (in 10 reviews)
  • Smallest flat screen tv we have ever seen. (in 1 review)
  • Great location with Beautiful grounds (in 4 reviews)
Cons -
  • "The hot water did not last very long, so we had to switch rooms." (in 4 reviews)
  • Coffee pot was left with used grounds and coffee in the pot. (in 1 review)
  • Decorative bed pillows still had sharp ends of the tags sticking (in 5 reviews)

Winchester Inn room booking info

Value for money

9.2

Location rating

9.9

Distance to city center

0.1 mi

Nearest Airport

Medford

Distance to airport

14.6 mi

Check in/Check out

Check in anytime after 4:00 PM, check out anytime before 11:00 AM

Cancellation/prepayment

Cancellation/prepayment policies vary by room type and provider.

Frequently asked questions

  • How far is Winchester Inn from Medford?

    If there is no traffic, the 14.6 mi drive between Medford and Winchester Inn should only take about 43min. If your hotel is in a more metropolitan area, you may see the driving time increase due to traffic.

  • What is the best way to get to Winchester Inn from Medford?

    If you intend on renting a car to travel from Medford to the hotel, you will have peace of mind knowing that Winchester Inn offers parking on site. Car rentals in the area typically go for $94/day for a base model rental. Another more common option is to just take a taxi or rideshare service from the airport to Winchester Inn. The nearest airport to the hotel is Medford.

  • Are there food options at Winchester Inn?

    There is a restaurant at Winchester Inn that can be used by visitors of the hotel. You can sit down or take food to go. Call the front desk at +1 541 488 1113 for kitchen hours. One of the easiest dining options for Ashland guests staying in Winchester Inn is to get room service, which is available to all hotel guests.

  • Does Winchester Inn have a pool?

    Judging by our data, Winchester Inn does not have a pool on site, but hotels regularly make additions and changes to their venues and do not always notify us. It would be best to call Winchester Inn at +1 541 488 1113.

  • How close is Winchester Inn to Ashland city center?

    The city center nearest to Winchester Inn is Ashland, which is 0.1 mi away from the hotel’s front door. There, you can find Thomas Theatre, which is a popular sight in the area.

  • What is the phone number for Winchester Inn?

    For questions regarding the hotel or your stay at Winchester Inn, call +1 541 488 1113.

  • Does Winchester Inn have Wi-Fi available?

    Yes, Winchester Inn has Wi-Fi available to hotel guests.

  • What time is check-out for Winchester Inn?

    The required check-out time is 11:00 AM. Please plan accordingly before your departure to avoid any penalties or fees.

  • How much is a room at Winchester Inn?

    Depending on the room type you prefer and your travel dates, the cost will differ. Average price per night at Winchester Inn, Ashland is $468, but you may find great deals as low as $239. You can find rates for your trip in the form above.

  • Is there laundry service in Winchester Inn?

    Yes, laundry services are accessible for guests staying at Winchester Inn, Ashland. Irons and ironing boards are included as featured amenities.

  • What is the distance from Winchester Inn, Ashland to Angus Bowmer Theater?

    Make sure to visit Angus Bowmer Theater during your stay at Winchester Inn, Ashland. It’s only 0.2 mi away!

  • Is Oregon Shakespeare Festival, Ashland close to Winchester Inn?

    Yes, Oregon Shakespeare Festival is only 0.2 mi from Winchester Inn.

  • How many operators does momondo search for hotels in Ashland?

    There are 314 operators available for hotels in Ashland as of July 2025.

  • When did momondo last update prices for hotels in Ashland?

    Prices for hotels in Ashland are updated daily.

Places of interest near Winchester Inn

Attractions in Ashland, Oregon curated by momondo

Winchester Inn location: 35 South 2nd Street, Ashland, OR 97520

Top landmarks

Lithia Springs Hotel0.1 mi
IOOF Building0.3 mi

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