Find a Hotel in Historic Downtown District

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Top hotels in Historic Downtown District

Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
$219 nightly
The price is $244 total per night from Apr 14 to Apr 15
$244 total
Apr 14 - Apr 15
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 ...
Lovely establishment, made to order breakfast, easy walking to theaters.

Reviewed on Apr 8, 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
$164 nightly
The price is $183 total per night from Apr 19 to Apr 20
$183 total
Apr 19 - Apr 20
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 ...
Easy check in, clean room, nice staff. We enjoyed our stay

Reviewed on Apr 11, 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
$100 nightly
The price is $112 total per night from Apr 14 to Apr 15
$112 total
Apr 14 - Apr 15
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, ...
Cindy who works in the Breakfast Room was particularly pleasant and helpful 😀 😊

Reviewed on Apr 12, 2026

Opens in a new windowStratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
$119 nightly
The price is $132 total per night from Apr 27 to Apr 28
$132 total
Apr 27 - Apr 28
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 ...
Just a block from the Shakespeare Festival, this hotel is ideally located. Room was clean as were common areas. Chairs in the room were cute, but could use some stuffing. Breakfast was good deal at $5…a step up from chain hotel breakfasts.

Reviewed on Apr 7, 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
$244 nightly
The price is $272 total per night from Apr 19 to Apr 20
$272 total
Apr 19 - Apr 20
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 has a great location, easy to walk to center of town. The breakfasts were very fresh and warm. They had 3 or 4 different EV chargers behind the lovely historic house.

Reviewed on Mar 31, 2026

Opens in a new windowMcCall House Boutique Inn
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
$96 nightly
The price is $108 total per night from Apr 19 to Apr 20
$108 total
Apr 19 - Apr 20
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 ...
Great

Reviewed on Apr 12, 2026

Opens in a new windowMy Place Hotel-Medford OR
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Apr 27 to Apr 28
$102 total
Apr 27 - Apr 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 ...
Rooms are comfortable and the staff is great.

Reviewed on Apr 13, 2026

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

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $121 total per night from Apr 19 to Apr 20
$121 total
Apr 19 - Apr 20
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 ...
Luna Cafe was understaffed

Reviewed on Apr 13, 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
$99 nightly
The price is $110 total per night from Apr 19 to Apr 20
$110 total
Apr 19 - Apr 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 ...
food good parking good

Reviewed on Apr 12, 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 Medford Airport

Rogue Regency Inn Medford Airport

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Rooms are comfortable and the staff is great."
A verified traveler stayed at Rogue Regency Inn Medford Airport
Rogue Regency Inn Medford Airport

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