Historic Downtown District Vacation Packages 2026 from $794

Historic Downtown District flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Ashland Hills Hotel & Suites

$794

per person

Dec 20 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) 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.

Winchester Inn

Historic Downtown District

$866

per person

Dec 20 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) 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

$865

per person

Dec 20 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Medford (MFR)

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 free WiFi in public areas. Enjoy the outdoor pool and free perks like buffet breakfast and free self parking.

Hanna's House by WanderLodges

Historic Railroad District

$831

per person

Dec 20 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Medford (MFR)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. A garden, laundry facilities, and a virtual front desk are also on offer.

The Peerless Hotel by WanderLodges

Historic Railroad District

$820

per person

Dec 20 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Medford (MFR)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Top Historic Downtown District hotels deals

The Bard's Inn, BW Signature Collection by Best Western

132 N Main Street Ashland OR

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$106 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

Ashland Springs Hotel

212 E Main St Ashland OR

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Dec 1 - Dec 2

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

Winchester Inn

35 S. 2nd St. Ashland OR

$168 nightly

$187 total

Nov 16 - Nov 17

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

$173 nightly

$193 total

Dec 3 - Dec 4

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

1907 Charmer, Perfect Downtown Location, So Clean!

Ashland OR

Get rates

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Compass by Margaritaville in Medford

2399 S Pacific Hwy Medford OR

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$181 total

Dec 2 - Dec 3

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 free WiFi in public areas. Enjoy the outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular Historic Downtown District attractions

Oregon Shakespeare Festival

9.2/10 (620 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.

See properties

Frequently asked questions

How much are vacation packages to Historic Downtown District?

Exciting adventures await you in Historic Downtown District, with Travelocity vacation packages from as little as $794. Offering both flights and hotels, these awesome deals make it easy to experience every corner of the globe.

Where can I get the best vacation package deals for Historic Downtown District?

It's simple — head to Travelocity. With as many as 400 partner airlines and 1,000,000 worldwide properties, it's easy to find a Historic Downtown District package deal that suits your needs.

Why should I book my Historic Downtown District vacation bundle with Travelocity?

Because you'll never roam alone if you secure your trip through us, and we offer round-the-clock customer support and top-quality service to boot. Add to that our Price Match Guarantee and tons of destinations to select from. It's our job to make your vacation as unforgettable as possible.

Will I save money on my Historic Downtown District car rental if I bundle it with a hotel or flight?

Certainly. And our Historic Downtown District vacation packages will help you do it. In only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and do your vacation your way. Looking for things to do? Add some activities or experiences to your package and save on those too.

Which airport is best for Historic Downtown District?

Historic Downtown District is serviced by two major airports — Rogue Valley Intl. Airport (MFR) and Klamath Falls Intl. Airport (LMT).

What is there to do in Historic Downtown District?

You'll be happy to know Historic Downtown District is teeming with incredible photo-ops, however Oregon Shakespeare Festival and Oregon Cabaret Theatre are two you shouldn't miss.