Historic Downtown District Vacation Packages 2025 from $810

Historic Downtown District flight + hotel vacation packages

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

Paschal Winery

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Springfield (SGF) to Medford (MFR)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.

A Cowslip's Belle Inn

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Springfield (SGF) to Medford (MFR)

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out.

Green Springs Inn

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Springfield (SGF) to Medford (MFR)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out, barbecue grills, and wedding services are also on offer.

Ashland Springs Hotel

Historic Downtown District

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Springfield (SGF) 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.

Winchester Inn

Historic Downtown District

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Springfield (SGF) 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.

Top Historic Downtown District hotels deals

Ashland Springs Hotel

212 E Main St, Ashland, OR

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$232 total

Jun 23 - Jun 24

Total includes 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

$159 nightly

$177 total

Jun 9 - Jun 10

Total includes taxes and fees

Free self parking is available and the hotel's front desk is staffed around-the-clock. 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

$221 nightly

$247 total

Jun 9 - Jun 10

Total includes 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

Get rates

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

$120 nightly

$135 total

Jun 15 - Jun 16

Total includes 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 continental breakfast each morning.

Pool

Hot Tub

Ashland Hills Hotel & Suites

2525 Ashland St, Ashland, OR

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$161 total

Jun 15 - Jun 16

Total includes 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 are available on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Historic Downtown District

View all properties

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

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 acclaimed theater scene.

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

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 $810. 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.