Deals on vacations and trips to Historic Downtown District
Historic Downtown District flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Wine Country Inn
Price was $378, price is now $285 per person
$285
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A garden, a picnic area, and express check-out are also on offer.
Winchester Inn
Historic Downtown District
Price was $820, price is now $599 per person
$599
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
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 self parking. A terrace, a garden, and dry cleaning are also on offer.
Compass by Margaritaville in Medford
Price was $468, price is now $369 per person
$369
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Ashland Hills Hotel & Suites
Price was $408, price is now $322 per person
$322
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
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 WiFi in public areas. Enjoy the gym and perks like free self parking.
Ashland Springs Hotel
Historic Downtown District
Price was $491, price is now $394 per person
$394
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
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 in public areas. Enjoy the sauna and perks like free self parking.
Top Historic Downtown District hotels deals
Ashland Springs Hotel
212 E Main St Ashland OR
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $134 total per night
$134 total
Nov 24 - Nov 25
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 in public areas. Enjoy the sauna and perks like free self parking.
Spa
Pet friendly
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $117 total per night
$117 total
Nov 24 - Nov 25
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 areas. A 24-hour business center, a garden, and luggage storage are also on offer.
Pool
Breakfast included
Winchester Inn
35 S. 2nd St. Ashland OR
$149 nightly
The price is $167 total per night
$167 total
Nov 25 - Nov 26
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 self parking. A terrace, a garden, and dry cleaning are also on offer.
Breakfast included
Parking included
McCall House Boutique Inn
153 Oak St Ashland OR
$190 nightly
The price is $212 total per night
$212 total
Dec 1 - Dec 2
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, a garden, and a lobby fireplace are also on offer.
Breakfast included
Parking included
Rogue Regency Inn and Suites
2300 Biddle Rd Medford OR
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $106 total per night
$106 total
Nov 24 - Nov 25
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 areas, and free airport shuttle. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Flagship Inn of Ashland
1193 Siskiyou Blvd Ashland OR
Free Cancellation
Reserve now, pay when you stay
$49 nightly
The price is $55 total per night
$55 total
Dec 6 - Dec 7
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 freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
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See all available properties in Historic Downtown District
View all propertiesLowest 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.
Popular places to visit
Oregon Shakespeare Festival
4.5/5(265 reviews)
You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
Allen Elizabethan Theatre
You can enjoy a show at Allen Elizabethan Theatre during your stay in Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.
Oregon Cabaret Theatre
4.5/5(47 reviews)
You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Frequently asked questions
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