Historic Downtown District Vacation Packages 2026/2026

Top Historic Downtown District hotels deals

Ashland Springs Hotel

212 E Main St Ashland OR

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Dec 17 - Dec 18

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

$117 total

Dec 10 - Dec 11

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

$158 nightly

$177 total

Jan 5 - Jan 6, 2026

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

$164 nightly

$183 total

Jan 4 - Jan 5, 2026

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

$99 nightly

$111 total

Dec 7 - Dec 8

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

$63 nightly

$71 total

Dec 10 - Dec 11

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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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.

Popular places to visit

Oregon Shakespeare Festival

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.

Thomas Theatre

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices.

Oregon Cabaret Theatre

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

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 . 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.