Winchester Inn

Rental with Tennis

3 stars
9.3
Wonderful
based on 567 reviews
567 verified ratings
35 South 2nd Street, Ashland, OR 97520
35 South 2nd Street, Ashland, OR
+1 541 488 1113
Wed 10/28
-
Thu 10/29
2 guests, 1 room
Deals from
$177
/Cheapest rate per night
Room type
Provider
Nightly total
Double room
$177
Standard room
$232
Queen room
$260
25 more Winchester Inn deals
25 more Winchester Inn deals
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Bedroom
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About Winchester Inn, Ashland

Cleanliness
9.6
Comfort
9.6
Location
9.8
Services
9.4
Staff
9.6
Value for money
9.0
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 room price & deals

Wed 10/28
-
Thu 10/29
Queen room
bed type unknown
$260
nightly with fees
1 queen bed
$268
nightly with fees
bed type unknown
$332
nightly with fees
Standard room
bed type unknown
$232
nightly with fees
bed type unknown
$315
nightly with fees
bed type unknown
$422
nightly with fees
Deluxe room
bed type unknown
$495
nightly with fees
bed type unknown
$550
nightly with fees
King room
bed type unknown
$308
nightly with fees
bed type unknown
$344
nightly with fees
bed type unknown
$367
nightly with fees
Double room
1 queen bed
$177
nightly with fees
bed type unknown
$214
nightly with fees
bed type unknown
$220
nightly with fees
*Total includes estimated local taxes & fees payable on check out.

Inn Amenities & Facilities

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

Winchester Inn Reviews

9.3
Wonderful
567 verified ratings
Wonderful
474
Very good
49
Good
19
Okay
10
Fair
3
Mediocre
1
Poor
11
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Winchester Inn room booking info

Value for money

9.0

Location rating

9.8

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 does Winchester Inn compare to other 3 star hotels in Ashland?

    Winchester Inn is $41 cheaper than the average 3 star hotel in Ashland. You can usually find a nightly rate of $174 when staying at Winchester Inn.

  • 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 43 mins. 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 $35/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.

  • 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 $384, but you may find great deals as low as $166. 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.

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

    There are 243 operators available for hotels in Ashland as of October 2026.

  • 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

  • Oregon Cabaret Theatre86 yd
  • Waterstone Spa120 yd
  • Lithia Springs Hotel148 yd
  • Ashland Library222 yd
  • Thomas Theatre237 yd
  • Elizabethan Stage - Allen Pavilion282 yd
  • Oregon Shakespeare Festival320 yd
  • Angus Bowmer Theater337 yd
  • IOOF Building0.3 mi
  • Lithia Park0.5 mi
  • ScienceWorks Hands-On Museum1.2 mi
  • Schneider Museum of Art1.2 mi

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