Find a Hotel in Historic Downtown District

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Top hotels in Historic Downtown District

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
$178 nightly
The price is $199 total per night from Nov 17 to Nov 18
$199 total
Nov 17 - Nov 18
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, ...
Great stay! Ambience was magical!

Reviewed on Nov 9, 2025

Opens in a new windowMcCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
$190 nightly
The price is $212 total per night from Nov 17 to Nov 18
$212 total
Nov 17 - Nov 18
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 ...
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on Oct 26, 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
$120 nightly
The price is $134 total per night from Nov 15 to Nov 16
$134 total
Nov 15 - Nov 16
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 ...
Love this hotel - super comfy bed. Only downside was elevator was glitching so we had to carry luggage up three flights. Other than that, top notch.

Reviewed on Nov 8, 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
$96 nightly
The price is $108 total per night from Nov 21 to Nov 22
$108 total
Nov 21 - Nov 22
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 ...
Room was very clean and modern looking, staff was very friendly. Good location close to the freeway, and there’s a coffee shop next door that’s pretty convenient. My only complaint was that the doors to the rooms, which are very big and heavy, don’t have anything to dampen/slow them down. Starting ...

Reviewed on Nov 6, 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
$91 nightly
The price is $102 total per night from Nov 15 to Nov 16
$102 total
Nov 15 - Nov 16
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 ...
Wonderful food in the pub Beds were great

Reviewed on Nov 11, 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
$118 nightly
The price is $132 total per night from Nov 16 to Nov 17
$132 total
Nov 16 - Nov 17
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 ...
Good, clean, comfortable

Reviewed on Nov 7, 2025

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
$109 nightly
The price is $122 total per night from Nov 17 to Nov 18
$122 total
Nov 17 - Nov 18
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 Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel

Reviewed on Nov 6, 2025

Opens in a new windowThe Bard's Inn, BW Signature Collection by Best Western
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
$52 nightly
The price is $59 total per night from Nov 18 to Nov 19
$59 total
Nov 18 - Nov 19
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 ...
The room was amazingly spacious and well furnished. Everything was clean and well organized for convenience and comfort with great amenities. I will definitely make this my place to stay from now on.

Reviewed on Nov 11, 2025

Opens in a new windowFlagship Inn of Ashland
Motel 6 Medford, OR - North

Motel 6 Medford, OR - North

2 out of 5
2400 Biddle Rd, Medford, OR
Fully refundable
$40 nightly
The price is $46 total per night from Nov 23 to Nov 24
$46 total
Nov 23 - Nov 24
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are ...
.

Reviewed on Nov 3, 2025

Opens in a new windowMotel 6 Medford, OR - North
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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

Flagship Inn of Ashland

Flagship Inn of Ashland

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"The room was amazingly spacious and well furnished. Everything was clean and well organized for convenience and comfort with great amenities. I will definitely make this my place to stay from now on."
A verified traveler stayed at Flagship Inn of Ashland
Flagship Inn of Ashland

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