Skip to main content

Featured Hotels Near Windsor

Filter by:

Star Rating

Review score

See the latest prices and deals by choosing your dates.
McCall House Boutique Hotel, hotel in Ashland

Located in Ashland, a 2-minute walk from Oregon Shakespeare Festival, McCall House Boutique Hotel has accommodations with a garden, free private parking and a shared lounge.

Incredibly easy to check in. Lovely attentive staff. The fresh chocolate cookies upon our early check-in, most welcomed. Great mattress and lovely linens. Every need was met and while we were in the carriage house south (upstairs) along the road, the noise was minimal, although a white noise machine would be helpful likely for some. The breakfast was simple (eggs, bacon, toast and fresh coffee) but great quality. Check out was seamless. 9.5/10. Would definitely recommend and will return.
Scored 9.8
9.8
Rated exceptional
Exceptional
23 reviews
Price from
$158
1 night, 2 adults
Bayberry Inn B&B and Oregon Wellness Retreat, hotel in Ashland

Located in Ashland, a 13-minute walk from Oregon Shakespeare Festival, Bayberry Inn B&B and Oregon Wellness Retreat provides accommodations with free bikes, free private parking, a garden and a shared...

The hosts are wonderful. The property is beautiful and extremely comfortable.
Scored 9.6
9.6
Rated exceptional
Exceptional
30 reviews
Price from
$294
1 night, 2 adults
Stratford Inn, hotel in Ashland

Stratford Inn is located in Ashland. Free Wi-Fi is provided in all rooms and a hot tub is available on site. Central Ashland is 5 minutes’ walk away.

Breakfast was beyond expectations. Location & price point ideal for our budget. Old school feel is not a problem as long as the cleanliness is good.
Scored 8.4
8.4
Rated very good
Very Good
1,479 reviews
Price from
$120
1 night, 2 adults
Callahan's Lodge, hotel in Ashland

Located in Ashland, 9.4 miles from Oak Knoll Golf Course, Callahan's Lodge has accommodations with a fitness center, free private parking, a garden and a shared lounge.

The house is amazing and an incredible size. Loved the house very much.
Scored 8.2
8.2
Rated very good
Very Good
580 reviews
Price from
$139
1 night, 2 adults
Holiday Inn Express Hotel & Suites Ashland, an IHG Hotel, hotel in Ashland

Featuring an indoor pool and a fitness center, Holiday Inn Express Hotel & Suites Ashland offers rooms with free Wi-Fi. Southern Oregon University is 1.4 mi away.

Beds and sheets comfortable as expected and why I booked Room ready slightly early
Scored 8.8
8.8
Rated excellent
Excellent
255 reviews
Price from
$122
1 night, 2 adults
Best Western Windsor Inn, hotel in Ashland

Offering English Tudor-style architecture, Best Western Windsor Inn is located in Ashland, Oregon. An outdoor swimming pool, a fitness center, and free WiFi access are featured here.

Scored 8.4
8.4
Rated very good
Very Good
507 reviews
Price from
$135
1 night, 2 adults
See more properties near Windsor

Top 10 trending hotels near Windsor

Discover our most popular hotels from the last 30 days

Enjoy breakfast at hotels near Windsor

  • McCall House Boutique Hotel
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 23 reviews

    Located in Ashland, a 2-minute walk from Oregon Shakespeare Festival, McCall House Boutique Hotel has accommodations with a garden, free private parking and a shared lounge.

    Immaculate. Great people. Location was perfect. Food incredible.

  • Stratford Inn
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 1,479 reviews

    Stratford Inn is located in Ashland. Free Wi-Fi is provided in all rooms and a hot tub is available on site. Central Ashland is 5 minutes’ walk away.

    The staff, the location, the room was very clean and cosy.

  • Ashland Springs Hotel
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 390 reviews

    Located less than a 5 minute walk to the site of Oregon Shakespeare Festival, this luxury Ashland, Oregon hotel offers a spa and farm to table fine dining.

    Our room was just enough…neat, tidy and comfortable.

  • Plaza Inn & Suites at Ashland Creek
    Scored 7.9
    7.9
    Rated good
    Good
     · 624 reviews

    Plaza Inn & Suites at Ashland Creek is set in downtown Ashland, 1969 feet from the Oregon Shakespeare Festival.

    Lots of packaged options for us to take on the go.

  • Winchester Inn
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 390 reviews

    Winchester Inn is set in Ashland, only 984 feet from Oregon Shakespeare Festival. Guests can enjoy the on-site bar and restaurant, featuring an outdoor patio. Free parking is also included.

    Travis was wonderful. I love the breakfast and garden!

  • Bayberry Inn B&B and Oregon Wellness Retreat
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 30 reviews

    Located in Ashland, a 13-minute walk from Oregon Shakespeare Festival, Bayberry Inn B&B and Oregon Wellness Retreat provides accommodations with free bikes, free private parking, a garden and a shared...

    The hosts are wonderful. The property is beautiful and extremely comfortable.

  • Callahan's Lodge
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 580 reviews

    Located in Ashland, 9.4 miles from Oak Knoll Golf Course, Callahan's Lodge has accommodations with a fitness center, free private parking, a garden and a shared lounge.

    Food was great fireplace inside the room nice hot tub

People are talking about Windsor! Explore guest hotel reviews featuring "Windsor"

  • From $150.53 per night
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 507 reviews
    The staff at Windsor Inn are the nicest people! I loved my stay ♥️ I had a migraine that day I checked in they were so kind when I asked to check in a little early. Ana in Ashland offered to help in any way she could. She made me feel at home. I highly recommend the Windsor Inn. I'll be back! Mucho obrigata girls!!
    Suzanne
    United States of America
  • From $150.53 per night
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 507 reviews
    I feel so welcome staying at the Windsor Inn. The staff is very friendly and thoughtful to me and my dog, Winslow.
    Kathy
    United States of America