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Top hotels in Historic Downtown District

Spacious 2 bedroom historic home with two king beds and kitchenette.

Spacious 2 bedroom historic home with two king beds and kitchenette.

Ashland OR
$324 nightly
The price is $347 total per night from Feb 23 to Feb 24
$347 total
Feb 23 - Feb 24
Total with taxes and fees
Stay at this apartment in Ashland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Allen Elizabethan Theatre and Angus Bowmer ...
Excellent location
Great location, nice place to stay. Could use a frying pan.

Reviewed on Apr 22, 2025

Opens in a new windowSpacious 2 bedroom historic home with two king beds and kitchenette.
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
$193 nightly
The price is $215 total per night from Feb 23 to Feb 24
$215 total
Feb 23 - Feb 24
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 ...
The room is fantastic!! Highly recommend!

Reviewed on Jan 15, 2026

Opens in a new windowWinchester Inn
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $163 total per night from Mar 1 to Mar 2
$163 total
Mar 1 - Mar 2
Total with taxes and fees
A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and ...
The staff were amazingly helpful and the room was very clean. Everyone was very accommodating when staying here with a pet for a night. I’d stay here again for sure!

Reviewed on Feb 22, 2026

Opens in a new windowCompass by Margaritaville in Medford
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $89 total per night from Mar 5 to Mar 6
$89 total
Mar 5 - Mar 6
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, ...
Extremely clean

Reviewed on Feb 22, 2026

Opens in a new windowStratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Feb 25 to Feb 26
$123 total
Feb 25 - Feb 26
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 ...
Clean room, really great breakfast!

Reviewed on Feb 19, 2026

Opens in a new windowAshland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
$119 nightly
The price is $133 total per night from Feb 23 to Feb 24
$133 total
Feb 23 - Feb 24
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, ...
It was an amazing stay! Exceptional in every way. And the breakfast was a lovely bonus. Too notch

Reviewed on Feb 20, 2026

Opens in a new windowMcCall House Boutique 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
$91 nightly
The price is $102 total per night from Feb 23 to Feb 24
$102 total
Feb 23 - Feb 24
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 ...
yes room was clean and big

Reviewed on Feb 22, 2026

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
$102 nightly
The price is $114 total per night from Feb 23 to Feb 24
$114 total
Feb 23 - Feb 24
Total with taxes and fees
This smoke-free hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free ...
Stayed here 5 times,. We like the property, pretty, pickle ball court, pool and jacuzzi and bikes to use an added plus. The Luna cafe is good. Nice location. Staff friendly and fresh baked chocolate cookies after 4:00! Sweet Touch. I would like to be able to stream. Would be nice to upgrade TV.

Reviewed on Feb 22, 2026

Opens in a new windowAshland Hills Hotel & Suites
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
$95 nightly
The price is $106 total per night from Feb 25 to Feb 26
$106 total
Feb 25 - Feb 26
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 ...
The first time we stayed at The Bard's Inn back in 2020 was an amazing experience. The room was extremely nice, service was great, food was great. This time, though, the room was very dingy, with minimal amenities. It looked as though nothing had been done with it in years. The food experience was ...

Reviewed on Feb 17, 2026

Opens in a new windowThe Bard's Inn, BW Signature Collection by Best Western
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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

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"yes room was clean and big"
A verified traveler stayed at Rogue Regency Inn and Suites
Rogue Regency Inn and Suites

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