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.
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
Price was $477, price is now $427 per person
$427
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A snack bar/deli, a picnic area, and a computer station are also on offer.
Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $1,573, price is now $1,217 per person
$1,217
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges

3 out of 5
Price was $1,611, price is now $1,407 per person
$1,407
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Medford (MFR)
A hot tub, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. 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 $751, price is now $657 per person
$657
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $859, price is now $758 per person
$758
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
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.

Top Historic Downtown District hotels deals

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
$169 nightly
The price is $188 total per night
$188 total
Aug 2 - Aug 3
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

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $226 total per night
$226 total
Aug 24 - Aug 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
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
$206 nightly
The price is $230 total per night
$230 total
Aug 3 - Aug 4
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
$306 nightly
The price is $341 total per night
$341 total
Aug 3 - Aug 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
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
Free Cancellation
Reserve now, pay when you stay
$182 nightly
The price is $203 total per night
$203 total
Aug 2 - Aug 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
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $128 total per night
$128 total
Aug 5 - Aug 6
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 buffet breakfast and free self parking.
Pool
Hot Tub
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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 $427. 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

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.
A display window with a large red flower and a sign reading "Oregon Shakespeare Festival Welcome Center".
A building corner with ornate architectural details and arched windows overlooking a cityscape.
A detailed bronze sculpture of a group of people, some with raised hands, against a tiled wall.
A street with a 'NO PARKING' sign, a 'VARNS' sign, and a 'JEWEL BOX' storefront.