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Best Western Windsor Inn

United States United States , Medford - OR - Ashland, 2520 Ashland Street
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Business hotels Hotels with spa

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Book your stay at Best Western Windsor Inn - You can pay with crypto or card

Meal plans

Available board options

BB

Bed & Breakfast

BED AND BREAKFAST

Breakfast is included with your stay.

HB

Half Board

Usually includes breakfast and one additional meal.

RO

Room Only

Accommodation only. Meals are usually not included.

FB

Full Board

Usually includes breakfast, lunch, and dinner.

Upon availability

Room options



Hotel Description


Stay at this Ashland, Oregon hotel conveniently located right off the I-5 in Southern Oregon. The Best Western Windsor Inn offers comfortable accommodations, full-service amenities, and unbeatable customer service at an affordable price.

This Ashland hotel boasts 91 recently remodeled guest rooms including suites and Jacuzzi® rooms. Each room offers premium bedding, cable tv, Keurig® coffee maker, mini fridge, and microwaves available upon request.

Enjoy an array of amenities including a continental breakfast, free Wi-Fi, a large outdoor swimming pool, a year-round outdoor hot tub, and an exercise facility. We also have four restaurants within walking distance of our hotel for your convenience.

As an added convenience, we now offer Electric Vehicle Charging on-site at no additional cost. The Best Western Windsor Inn is only a 10-minute drive from downtown Ashland, home of the Oregon Shakespeare Festival, Lithia Park, and shopping.

The Best Western Windsor Inn is the perfect way to enjoy a quiet and relaxing stay in Ashland, Oregon. Relax outside among our rose gardens and enjoy the views of the surrounding Ashland hills.

During the summer months enjoy rafting down the Rogue River, while in the winter Mt. Ashland offers fantastic skiing.

Our hotel also offers a great stopping point on your way to visit Crater Lake, just one hour and 30 minutes from Ashland. The friendly, helpful staff at the Best Western Windsor Inn hotel is ready to ensure a fun-filled memorable stay in Ashland, Oregon.

Make a reservation today.


Facilities


Total number of rooms
Number of floors (main building)
Suites
hotel
Small pets allowed (under 5 kg)
Large pets allowed (over 5 kg)
Wheelchair-accessible
Car park
24-hour reception
Check-in hour
Check-out hour
Wired Internet
Wi-fi
Transfer service
Laundry service
24-hour security
Air conditioning in public areas
Smoke detector
Lift access
Garden
Gym
Newspapers
Luggage room
Towels and bed linen
Smoking area
Photocopier
Business centre
Outdoor freshwater pool
Game room
Hot tub
Spa centre
Breakfast
Non-smoking establishment
Fitness
Best Western - We Care Clean

Hotels Nearby

Or browse the Interactive Map to find hotels around Best Western Windsor Inn


The Village Suites at Ashland Hills
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The Village Suites at Ashland Hills
Hotel Details

ASHLAND, 2525 Ashland St

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After a day on the slopes, unwind at this Ashland hotel with amenities including outdoor tennis courts, an outdoor pool, and a complimentary ski shuttle. Enjoy dining at the restaurant or snacks at the coffee shop/cafe.

Stay connected with complimentary Wi-Fi and enjoy cable programming on your flat-screen TV. The hotel also offers a business center, conference facilities, and free self-parking.

Local attractions include Southern Oregon University (1. 3 mi) and the Oregon Shakespeare Festival (3.

1 mi).

Pay with crypto or card

3 STARS

The Village Suites at Ashland Hills

ASHLAND, 2525 Ashland St | Show on Google

~ 0.08 km from Best Western Windsor Inn

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Relax Inn At Ashland
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Relax Inn At Ashland
Hotel Details

ASHLAND, 535 Clover Lane

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A stay at Relax Inn At Ashland places you in the heart of Ashland, within a 5-minute drive of Southern Oregon University and Schneider Museum of Art. This hotel is 2 mi (3.

2 km) from ScienceWorks Hands-On Museum and 2. 3 mi (3.

6 km) from Cascade Range. This hotel features snowboarding nearby, downhill skiing nearby, and cross-country skiing nearby.

Recreational activities include bicycle rentals nearby and hiking/biking trails nearby. Featured amenities include a 24-hour front desk and coffee/tea in a common area.

Free self parking is available onsite. Make yourself at home in one of the 18 air-conditioned guestrooms.

Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers.

Conveniences include desks and blackout drapes/curtains, as well as phones with free local calls.

Pay with crypto or card

3 STARS

Relax Inn At Ashland

ASHLAND, 535 Clover Lane | Show on Google

~ 0.19 km from Best Western Windsor Inn

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Holiday Inn Express Hotel & Suites Ashland
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Holiday Inn Express Hotel & Suites Ashland
Hotel Details

ASHLAND, 565 Clover Lane

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Discover Ashland, Oregon, from the ideally located Holiday Inn Express. Home to the renowned Oregon Shakespeare Festival, Ashland offers a vibrant blend of culture, cuisine, and outdoor adventures.

Our hotel provides the perfect base for exploring this beautiful and culturally rich area. Explore downtown Ashland's art galleries, boutiques, and excellent restaurants with ease.

Spend a day in scenic Lithia Park, hike or ski at Mt. Ashland, or discover the nearby Pacific Crest Trail.

White-water rafting and mountain biking enthusiasts will find plenty to enjoy, while wine lovers can explore the numerous local vineyards. The Oregon Shakespeare Festival offers world-class theatre from February to November.

Business travelers will appreciate our proximity to local companies and Southern Oregon University. Medford, OR is just 12 miles away.

Enjoy free high-speed Wi-Fi, our complimentary hot Express Start Breakfast Bar each morning, an indoor pool, whirlpool, and on-site Fitness Center.

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3 STARS

Holiday Inn Express Hotel & Suites Ashland

ASHLAND, 565 Clover Lane | Show on Google

~ 0.26 km from Best Western Windsor Inn

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Rodeway Inn Ashland
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Rodeway Inn Ashland
Hotel Details

ASHLAND, 2359 Ashland Street

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When all you need is a solid deal on a simple stay, the pet-friendly Rodeway Inn hotel in Ashland, OR is just what you are looking for. Our hotel is located off Interstate 5 in the heart of Rogue Valley near attractions like Mt.

Ashland, Lithia Park and the Siskiyou National Forest. Enjoy amenities like free continental breakfast, free WiFi, a seasonal outdoor pool and copy and fax services.

Guest rooms include refrigerators, microwaves, coffee makers, hair dryers, irons and ironing boards. Also, earn rewards including free nights and gift cards with our Choice Privileges Rewards program.

Pay with crypto or card

3 STARS

Rodeway Inn Ashland

ASHLAND, 2359 Ashland Street | Show on Google

~ 0.54 km from Best Western Windsor Inn

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Oak Hill Bed & Breakfast
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Oak Hill Bed & Breakfast
Hotel Details

ASHLAND, 2190 Siskiyou Blvd

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Located in Ashland, Oak Hill Bed & Breakfast is a 3-minute drive from Southern Oregon University and 6 minutes from North Mountain Park. This bed & breakfast is 2.

2 mi (3. 5 km) from Ashland Library and 2.

3 mi (3. 8 km) from Oregon Cabaret Theatre.

Take in the views from a garden and make use of amenities such as complimentary wireless Internet access and concierge services. Additional features at this bed & breakfast include ski storage and a fireplace in the lobby.

Featured amenities include express check-in, express check-out, and luggage storage. Free self parking is available onsite.

A complimentary full breakfast is served daily from 8:00 AM to 10:00 AM. Treat yourself to a stay in one of the 6 individually decorated guestrooms, featuring fireplaces.

Complimentary wireless Internet access is available to keep you connected. Conveniences include complimentary bottled water and fans, and housekeeping is provided daily.

Pay with crypto or card

3 STARS AND A HALF

Oak Hill Bed & Breakfast

ASHLAND, 2190 Siskiyou Blvd | Show on Google

~ 1.48 km from Best Western Windsor Inn

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Cedarwood Inn of Ashland
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Cedarwood Inn of Ashland
Hotel Details

ASHLAND, 1801 Siskiyou Blvd

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Located in a quiet area of Ashland, this family-owned inn is less than two miles from the town centre. The property offers a range of recreational facilities, including both an indoor and an outdoor swimming pool, a sauna, and a steam room.

Guests benefit from complimentary on-site parking and free Wi-Fi access. All rooms are equipped with air conditioning, a flat-screen television, a microwave, and a refrigerator.

The inn is conveniently situated just 1 km from Southern Oregon University and 2 miles from the Oregon Shakespeare Festival. Additional features include on-site barbecue grills and a business centre.

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3 STARS

Cedarwood Inn of Ashland

ASHLAND, 1801 Siskiyou Blvd | Show on Google

~ 1.7 km from Best Western Windsor Inn

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Timbers Motel
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Timbers Motel
Hotel Details

CLEVELAND, 1450 Ashland Street

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The hotel comprises 29 cosy rooms. Visitors may take advantage of the Wi-Fi connection throughout.

Timbers Motel does not offer 24-hour reception.

Pay with crypto or card

2 STARS

Timbers Motel

CLEVELAND, 1450 Ashland Street | Show on Google

~ 2.32 km from Best Western Windsor Inn

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Flagship Inn of Ashland
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Flagship Inn of Ashland
Hotel Details

ASHLAND, 1193 Siskiyou Blvd

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Enjoy recreation amenities such as a seasonal outdoor pool or take in the view from a garden. Additional amenities at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.

Enjoy a satisfying meal at La Casa Del Pueblo serving guests of Flagship Inn of Ashland. A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.

Featured amenities include coffee/tea in a common area and a vending machine. Free self parking is available onsite.

Make yourself at home in one of the 61 air-conditioned rooms featuring refrigerators and microwaves. 40-inch flat-screen televisions with cable programming provide entertainment, while wireless internet access (surcharge) keeps you connected.

Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, and housekeeping is provided on request.

Distances are displayed to the nearest 0. 1 mile and kilometer.

Pay with crypto or card

3 STARS

Flagship Inn of Ashland

ASHLAND, 1193 Siskiyou Blvd | Show on Google

~ 2.65 km from Best Western Windsor Inn

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Ashland Motel - University
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Ashland Motel - University
Hotel Details

ASHLAND, 1145 Siskiyou Blvd

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A stay at Ashland Motel - University places you in the heart of Ashland, steps from Southern Oregon University and a 3-minute drive from North Mountain Park. This motel is 1 mi (1.

6 km) from Ashland Library and 1. 1 mi (1.

8 km) from Oregon Cabaret Theatre. Take in the views from a garden and make use of amenities such as complimentary wireless Internet access.

The front desk is staffed during limited hours. Free self parking is available onsite.

Make yourself at home in one of the 26 air-conditioned rooms featuring refrigerators and microwaves. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless Internet access keeps you connected.

Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers, and housekeeping is provided daily.

Pay with crypto or card

2 STARS

Ashland Motel - University

ASHLAND, 1145 Siskiyou Blvd | Show on Google

~ 2.75 km from Best Western Windsor Inn

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Stratford Inn
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Stratford Inn
Hotel Details

Ashland, 555 Siskiyou Blvd

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Take advantage of recreation opportunities including an indoor pool and a spa tub. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room.

To-go breakfasts are available daily from 7:00 AM to 10:00 AM for a fee. Featured amenities include a 24-hour business center, a 24-hour front desk, and multilingual staff.

Free self parking is available onsite. Make yourself at home in one of the 53 air-conditioned rooms featuring refrigerators and LCD televisions.

Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers.

Conveniences include desks and microwaves, as well as phones with free local calls. Distances are displayed to the nearest 0.

1 mile and kilometer. Ashland Library - 0.

4 km / 0. 2 mi- Oregon Cabaret Theatre - 0.

7 km / 0. 5 mi- Lithia Park - 0.

8 km / 0. 5 mi- Southern Oregon University - 0.

9 km / 0. 5 mi- Oregon Shakespeare Festival - 0.

9 km / 0. 6 mi- Allen Elizabethan Theatre - 0.

9 km / 0. 6 mi- Angus Bowmer Theatre - 0.

9 km / 0. 6 mi- Thomas Theatre - 0.

9 km / 0. 6 mi- North Mountain Park - 1.

6 km / 1 mi- Schneider Museum of Art - 1. 7 km / 1.

1 mi- ScienceWorks Hands-On Museum - 2 km / 1. 2 mi- Ashland Dog Park - 2.

9 km / 1. 8 mi- Weisinger Family Winery - 4.

9 km / 3. 1 mi- Grizzly Peak Winery - 5.

5 km / 3. 4 mi- Rogue River-Siskiyou National Forest - 8.

9 km / 5. 6 mi.

The preferred airport for Stratford Inn is Rogue Valley Intl. Airport (MFR) - 25.

6 km / 15. 9 miLocated in Ashland (Siskiyou-Hargadine Historic District), Stratford Inn is a 4-minute walk from Ashland Library and 9 minutes by foot from Oregon Cabaret Theatre.

This hotel is 0. 5 mi (0.

9 km) from Southern Oregon University and 0. 6 mi (0.

9 km) from Lithia Park.

Pay with crypto or card

4 STARS

Stratford Inn

Ashland, 555 Siskiyou Blvd | Show on Google

~ 3.76 km from Best Western Windsor Inn

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Ashland Springs Hotel
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Ashland Springs Hotel
Hotel Details

ASHLAND, E Main St, 212

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Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. Take advantage of recreational amenities such as a sauna and fitness center.

This Beaux-Arts hotel also features complimentary wireless internet access, concierge services, and gift shops/newsstands. Enjoy a satisfying meal at LARKS, serving guests of Ashland Springs Hotel.

Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:30 am to 10 am.

Featured amenities include a business center, express check-out, and complimentary newspapers in the lobby. Planning an event in Ashland?

This hotel has 5, 705 square feet (530 square meters) of space, consisting of a conference center and meeting rooms. Free self-parking is available on-site.

Stay in one of the 70 guest rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Frette Italian sheets.

Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature rainfall showerheads and complimentary toiletries.

Distances are displayed to the nearest 0. 1 mile and kilometer.

Oregon Cabaret Theatre - 0. 1 km / 0.

1 mi; Allen Elizabethan Theatre - 0. 2 km / 0.

1 mi; Angus Bowmer Theatre - 0. 2 km / 0.

1 mi; Thomas Theatre - 0. 2 km / 0.

1 mi; Oregon Shakespeare Festival - 0. 2 km / 0.

1 mi; Lithia Park - 0. 3 km / 0.

2 mi; Ashland Library - 0. 3 km / 0.

2 mi; Southern Oregon University - 1. 4 km / 0.

9 mi; North Mountain Park - 1. 6 km / 1 mi; Schneider Museum of Art - 2.

3 km / 1. 4 mi; ScienceWorks Hands-On Museum - 2.

4 km / 1. 5 mi; Weisinger Family Winery - 5.

5 km / 3. 4 mi; Grizzly Peak Winery - 5.

6 km / 3. 5 mi; Talent Library - 9 km / 5.

6 mi; Rogue River-Siskiyou National Forest - 9. 5 km / 5.

9 mi. The preferred airport for Ashland Springs Hotel is Rogue Valley International Airport (MFR) - 25.

1 km / 15 mi.

Pay with crypto or card

3 STARS

Ashland Springs Hotel

ASHLAND, E Main St, 212 | Show on Google

~ 4.29 km from Best Western Windsor Inn

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Mccall House Boutique Inn
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Mccall House Boutique Inn
Hotel Details

Ashland, 153 Oak St

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Enjoy a central Ashland location at the Victorian McCall House Boutique Inn, steps from Lithia Park and a short walk from the Oregon Shakespeare Festival. This B&B offers complimentary Wi-Fi, concierge services, and daily full breakfast.

Relax in one of the 10 air-conditioned rooms featuring smart TVs and designer toiletries. Amenities include a business center, free parking, and a charming lobby with a fireplace.

Pay with crypto or card

4 STARS

Mccall House Boutique Inn

Ashland, 153 Oak St | Show on Google

~ 4.48 km from Best Western Windsor Inn

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Plaza Inn & Suites at Ashland Creek
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Plaza Inn & Suites at Ashland Creek
Hotel Details

ASHLAND, 98 Central Ave

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Enjoy recreational amenities such as a 24-hour fitness center, a terrace, and a garden. This hotel also features complimentary Wi-Fi, concierge services, and gift shops/newsstands.

Start your day with a complimentary continental breakfast served from 7:00 AM to 10:00 AM. Business travelers appreciate the business center and complimentary wired internet access.

Free self-parking is available onsite. The 92 guest rooms offer refrigerators, microwaves, and private bathrooms with shower/tub combinations, hair dryers, and toiletries.

Stay connected with complimentary wired and wireless internet access and enjoy cable programming. Desks, coffee/tea makers, and phones with free local calls add extra convenience.

Located in Ashland's shopping district, Plaza Inn & Suites at Ashland Creek is within a 10-minute walk of Lithia Park and the Oregon Shakespeare Festival. Other nearby attractions include the Oregon Cabaret Theatre (0.

5 mi) and the Ashland Library (0. 6 mi).

The preferred airport is Rogue Valley International Airport (MFR), 15. 2 miles away.

Pay with crypto or card

3 STARS

Plaza Inn & Suites at Ashland Creek

ASHLAND, 98 Central Ave | Show on Google

~ 4.65 km from Best Western Windsor Inn

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The Bard'S Inn, Bw Signature Collection
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The Bard'S Inn, Bw Signature Collection
Hotel Details

Ashland, 132 N Main Street

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Nestled in the heart of downtown Ashland, The Bard's Inn, BW Signature Collection is located just two blocks from the historic plaza. When you stay with us you will be within short walking distance of the Oregon Shakespeare Festival, Oregon Cabaret Theatre, beautiful Lithia Park, fine dining, art galleries, and boutique shopping.

Pay with crypto or card

3 STARS

The Bard'S Inn, Bw Signature Collection

Ashland, 132 N Main Street | Show on Google

~ 4.7 km from Best Western Windsor Inn

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Lithia Springs Resort
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Lithia Springs Resort
Hotel Details

ASHLAND, 2165 W Jackson Rd

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Relax and unwind with massages, body treatments, and facials. If you're looking for recreational opportunities, you'll find an outdoor pool, a spa tub, and bicycles to rent.

This bed & breakfast also features complimentary wireless internet access, concierge services, and gift shops/newsstands. Grab a bite from the snack bar/deli serving guests of Lithia Springs Resort.

A complimentary buffet breakfast is served daily from 8 AM to 10 AM. Featured amenities include complimentary wired internet access, a business center, and dry cleaning/laundry services.

Free self parking is available onsite. Make yourself at home in one of the 38 individually decorated guestrooms, featuring refrigerators and microwaves.

Your bed comes with down comforters and Frette Italian sheets. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected.

Pay with crypto or card

3 STARS

Lithia Springs Resort

ASHLAND, 2165 W Jackson Rd | Show on Google

~ 7.75 km from Best Western Windsor Inn

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Comfort Inn & Suites Ashland
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Comfort Inn & Suites Ashland
Hotel Details

Ashland, 434 S. Valley View Road

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Behind every great day is a great night at the Comfort Inn and Suites in Ashland, OR, conveniently located near the Oregon Shakespeare Festival. We are near Lithia Park and a short drive from Mt.

Ashland Ski Area. Enjoy amenities like a full breakfast, free WiFi, a business center, heated pool and more.

Rooms include coffee makers, desks, hair dryers, irons, ironing boards and more. Earn rewards with every stay with our Choice Privileges Rewards program.

Pay with crypto or card

2 STARS AND A HALF

Comfort Inn & Suites Ashland

Ashland, 434 S. Valley View Road | Show on Google

~ 7.8 km from Best Western Windsor Inn

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Callahan S Mountain Lodge
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Callahan S Mountain Lodge
Hotel Details

ASHLAND, 7100 Old Highway 99 South

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Located in Ashland, Callahan's Mountain Lodge is connected to the convention center, within a 15-minute drive of Southern Oregon University and Schneider Museum of Art. This family-friendly lodge is 9.8 mi (15.8 km) from Mount Ashland Ski Area and 11.2 mi (18 km) from Bull Gap Lower Trailhead.

Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless Internet access. This lodge also features concierge services, an arcade/game room, and ski storage.

The complimentary ski shuttle makes getting to the slopes a breeze. Featured amenities include complimentary wired Internet access, limo/town car service, and express check-out.

Planning an event in Ashland? This lodge has facilities measuring 1800 square feet (167 square meters), including a conference center.

A roundtrip airport shuttle is provided for a surcharge (available on request), and free self parking is available onsite. Enjoy American cuisine at Callahan's Mountain Lodge, a family restaurant which features a bar/lounge and a garden view.

You can also stay in and take advantage of the room service (during limited hours). Cooked-to-order breakfasts are available daily from 8 AM to 11 AM for a fee.

Make yourself at home in one of the 19 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets.

60-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless Internet access keeps you connected. Private bathrooms with separate bathtubs and showers feature jetted bathtubs and complimentary toiletries.

Pay with crypto or card

3 STARS

Callahan S Mountain Lodge

ASHLAND, 7100 Old Highway 99 South | Show on Google

~ 13.44 km from Best Western Windsor Inn

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Americas Best Value Inn Phoenix Ashland
Quick Infos and Images
Americas Best Value Inn Phoenix Ashland
Hotel Details

Phoenix, 300 Pear Tree Lane

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Located in Phoenix, Americas Best Value Inn Phoenix Medford is a perfect starting point from which to explore Phoenix (OR). Both business travelers and tourists can enjoy the hotel's facilities and services.

Service-minded staff will welcome and guide you at the Americas Best Value Inn Phoenix Medford. Comfortable guestrooms ensure a good night's sleep with some rooms featuring facilities such as television LCD/plasma screen, air conditioning, heating, wake-up service, soundproofing.

The hotel offers various recreational opportunities. Americas Best Value Inn Phoenix Medford is an excellent choice from which to explore Phoenix (OR) or to simply relax and rejuvenate.

Pay with crypto or card

2 STARS

Americas Best Value Inn Phoenix Ashland

Phoenix, 300 Pear Tree Lane | Show on Google

~ 16.01 km from Best Western Windsor Inn

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