Find a Hotel in Historic Downtown District

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top hotels in Historic Downtown District

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
$229 nightly
The price is $255 total per night from Sep 28 to Sep 29
$255 total
Sep 28 - Sep 29
Total with taxes and fees
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A business center, ...
Comfy, cozy and convenient
"Wonderful place in a very convenient location within easy walking distance of OSF and a range of food, drink and shopping. Very comfortable and cozy, with a friendly, helpful staff."

Reviewed on Aug 30, 2025

Opens in a new windowMcCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
$223 nightly
The price is $249 total per night from Sep 29 to Sep 30
$249 total
Sep 29 - Sep 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free ...
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"

Reviewed on Sep 16, 2025

Opens in a new windowWinchester Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St, Ashland, OR
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $211 total per night from Sep 28 to Sep 29
$211 total
Sep 28 - Sep 29
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center and free WiFi ...
"Toilet doesn’t flush all the way unless you keep holding the handle down and then you have to pull up on the handle or it keeps running."

Reviewed on Sep 18, 2025

Opens in a new windowAshland Springs Hotel
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
$104 nightly
The price is $118 total per night from Oct 8 to Oct 9
$118 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and ...
"."

Reviewed on Sep 18, 2025

Opens in a new windowMy Place Hotel-Medford OR
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
$120 nightly
The price is $135 total per night from Sep 27 to Sep 28
$135 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"Elevators are only on 1 end of the entire complex"

Reviewed on Sep 18, 2025

Opens in a new windowRogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $156 total per night from Sep 28 to Sep 29
$156 total
Sep 28 - Sep 29
Total with taxes and fees
2 outdoor tennis courts, an outdoor pool, and a hot tub are all featured at this smoke-free hotel. There's a free ski shuttle, and ski passes and ski storage ...
Nice hotel in Ashland
"Cute, clean hotel right off of I-5. Easy to find. Friendly staff and nice grounds"

Reviewed on Sep 18, 2025

Opens in a new windowAshland Hills Hotel & Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Oct 26 to Oct 27
$90 total
Oct 26 - Oct 27
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate ...
"University campus right across the street. Place to charge an electric car near the student dining hall within walking distance. Free Charge Point station."

Reviewed on Sep 19, 2025

Opens in a new windowFlagship Inn of Ashland
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
$125 nightly
The price is $139 total per night from Oct 19 to Oct 20
$139 total
Oct 19 - Oct 20
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public ...
"Great location!"

Reviewed on Sep 22, 2025

Opens in a new windowThe Bard's Inn, BW Signature Collection by Best Western
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Oct 24 to Oct 25
$94 total
Oct 24 - Oct 25
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Enjoy the gym and free perks like continental breakfast and free self ...
"We love using the hot tub and our room is always comfortable"

Reviewed on Sep 22, 2025

Opens in a new windowQuality Inn & Suites Medford Airport
Don't see what you're looking for?
See all available properties in Historic Downtown District
View all properties
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.

Historic Downtown District Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Historic Downtown District area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Historic Downtown District to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Historic Downtown District are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Historic Downtown District hotel reviews by fellow wanderers