Hotels Near
Historic Downtown District

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Featured Historic Downtown District Hotels

Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular ...
9/10 Wonderful! (1,493 reviews)
"WHAT WE LIKED: Close enough to walk to downtown shops, restaurants, and to the play we wanted to see. The breakfast includes gluten free bread, the best I've ever tried. The dining area is spacious,and relaxed, with a loveable attendant named Cindy. I'm sure you'll be charmed by her sweet nature. ..."

Reviewed on Apr 24, 2024

Stratford Inn
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this 3-star spa hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
"Right next to Oregon Shakespeare Festival. Great bookstores and restaurants. Nice fireplace in lobby."

Reviewed on Apr 22, 2024

Ashland Springs Hotel
The Bard's Inn, BW Signature Collection by Best Western
The Bard's Inn, BW Signature Collection by Best Western
2.5 out of 5
132 N Main Street, Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
Convenient location
"The hotel is all very tired and could do with a facelift and new interior decoration. We stay there for the convenient location. We can walk to the plays, restaurants and shopping and never need to drive once we are there."

Reviewed on Apr 23, 2024

The Bard's Inn, BW Signature Collection by Best Western
McCall House Boutique Inn
McCall House Boutique Inn
4 out of 5
153 Oak St, Ashland, OR
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Allen Elizabethan Theatre and Angus Bowmer Theatre ...
9.8/10 Exceptional! (229 reviews)
"McCall House is a beautiful, historic property in an excellent location close to the OSF plays and Ashland’s many top restaurants."

Reviewed on Mar 31, 2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (199 reviews)
A girls day out
"Nice place, amazing food and customer service"

Reviewed on Mar 17, 2024

Winchester Inn
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,095 reviews)
"Awesome"

Reviewed on Apr 24, 2024

Rogue Regency Inn and Suites
My Place Hotel-Medford OR
My Place Hotel-Medford OR
3 out of 5
580 Airport Rd, Medford, OR
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Medford. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the convenient ...
8.8/10 Excellent! (836 reviews)
"Very nice room with great amenities. The staff is very accommodating. I would stay here again."

Reviewed on Apr 22, 2024

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this ski hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
9/10 Wonderful! (1,543 reviews)
"retro look is great"

Reviewed on Apr 23, 2024

Ashland Hills Hotel & Suites
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
8.6/10 Excellent! (1,005 reviews)
Great place for dogs
"Great friendly staff who welcome you at the front desk. Hotel is conveniently located and dog friendly ,we were travelling with 2 large dogs. Room was very clean,very quiet despite being close to highway. Thank you for our great stay. We will be back. Highly recommend."

Reviewed on Apr 19, 2024

Comfort Inn & Suites
Holiday Inn Express Hotel & Suites Medford-Central Point, an IHG Hotel
Holiday Inn Express Hotel & Suites Medford-Central Point, an IHG Hotel
2.5 out of 5
285 Peninger Rd, Central Point, OR
Fully refundable
Stay at this business-friendly hotel in Central Point. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
"Only stayed one night while traveling through, room was very clean and decent size bathroom, nice staff."

Reviewed on Apr 21, 2024

Holiday Inn Express Hotel & Suites Medford-Central Point, an IHG Hotel
Springhill Suites By Marriott Medford Airport
Springhill Suites By Marriott Medford Airport
3 out of 5
3519 HEATHROW WAY, Medford, OR
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (449 reviews)
"The property was very nice, it was so clean. The room was great. The staff was so friendly and kind. Their gym was great and had a lot of equipment. The location was perfect, it is in a quiet area, but also it's not far away from stores and restaurants. We were so happy with our experience, we will ..."

Reviewed on Apr 22, 2024

Springhill Suites By Marriott Medford Airport
Callahan's Mountain Lodge
Callahan's Mountain Lodge
3 out of 5
7100 Old Highway 99 South, Ashland, OR
Fully refundableReserve now, pay when you stay
Stay at this 3-star family-friendly lodge in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the helpful staff ...
8.8/10 Excellent! (1,001 reviews)
"Charming lodge stay - like a cabin! Spacious, with balcony beautiful, X-Large jetted tub, and fireplace, robes. Perfect overnight stay. Restaurant food, good! Complimentary breakfast simple. Service friendly and efficient. Great value!! Will definitely stay again."

Reviewed on Apr 23, 2024

Callahan's Mountain Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels in Historic Downtown District

Ashland is a city that has a lot going on, but you have your sights set on Historic Downtown District. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Historic Downtown District has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Historic Downtown District hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Ashland so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Historic Downtown District underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Historic Downtown District city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Historic Downtown District cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Historic Downtown District at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $80
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Historic Downtown District hotel you want, book it, and never look back. Because your great escape is ahead of you.