Deals on vacations and trips to Historic Downtown District

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Historic Downtown District flight + hotel vacation packages

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

Wine Country Inn

3 out of 5
Price was $941, price is now $687 per person
$687
per person
May 12 - May 19
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $1,103, price is now $796 per person
$796
per person
May 12 - May 19
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Jacksonville Mountain Retreat

Jacksonville Mountain Retreat

2 out of 5
Save 100% on your flight
Price was $3,761, price is now $2,874 per person
$2,874
per person
May 12 - May 19
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
This vacation home features free WiFi in public areas, a garden, and barbecue grills.
Quail Run River View Cottage

Quail Run River View Cottage

2 out of 5
Save 100% on your flight
Price was $2,154, price is now $1,685 per person
$1,685
per person
May 12 - May 19
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
This vacation home features free WiFi in public areas, a garden, and barbecue grills.
Quail Run Mountain View Cottage

Quail Run Mountain View Cottage

2 out of 5
Save 100% on your flight
Price was $1,926, price is now $1,518 per person
$1,518
per person
May 12 - May 19
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
Free WiFi in public areas is available at this vacation home.

Top Historic Downtown District hotels deals

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
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
Mar 11 - Mar 12
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

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

2.5 out of 5
132 N Main Street Ashland OR
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $110 total per night
$110 total
Mar 9 - Mar 10
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

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
$211 nightly
The price is $235 total per night
$235 total
Mar 9 - Mar 10
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

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
$143 nightly
The price is $159 total per night
$159 total
Apr 1 - Apr 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
Spacious 2 bedroom historic home with two king beds and kitchenette.

Spacious 2 bedroom historic home with two king beds and kitchenette.

Ashland OR
$368 nightly
The price is $396 total per night
$396 total
Mar 9 - Mar 10
Total with taxes and fees
Stay at this apartment in Ashland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Allen Elizabethan Theatre and Angus Bowmer Theatre are located nearby.
Air conditioning
Outdoor Space
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $110 total per night
$110 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a terrace, and a library are also on offer.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Historic Downtown District
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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

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

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.

Oregon Shakespeare Festival

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.

Oregon Cabaret Theatre

Thomas Theatre

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

Thomas Theatre

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 $687. 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.

Photos of local treasures

Browse Historic Downtown District vacation photos for more inspiration

Landmark building in Ashland Oregon.
Landmark building in Ashland Oregon.
Ashland is all about the Shakespeare down to the poppy #Red
We had a corner queen on the 8th floor and this is a close look at the neoclassical gothic architecture from our bedroom window
I always check out the local chamber of commerce when I land in a town I haven’t been to before. Ashland Oregon Chamber of Commerce is unique in that it’s beside this amazing bronze Shakespeare statue.