Historic Railroad District Vacation Packages

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Top Holiday Package Deals in Historic Railroad District

Price found within the past 48 hours. Click for updated prices.
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
Price was CA $902, price is now CA $797 per person
CA $797
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Medford (MFR)
8.8/10 Excellent! (1,169 reviews)
Clean room, plenty of firewood to use in our room, dinner selection was great. Snowed in for 4 days Lodge stayed open without failure !

Reviewed on Feb 24, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was CA $1,084, price is now CA $925 per person
CA $925
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Medford (MFR)
9.8/10 Exceptional! (40 reviews)
Lovely yard courtyard area with koi pond

Reviewed on Aug 25, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was CA $1,305, price is now CA $1,148 per person
CA $1,148
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
It was an amazing stay! Exceptional in every way. And the breakfast was a lovely bonus. Too notch

Reviewed on Feb 20, 2026

Wine Country Inn

Wine Country Inn

3 out of 5
Price was CA $928, price is now CA $819 per person
CA $819
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Medford (MFR)
9.4/10 Exceptional! (1,002 reviews)
Fantastic rooms and areas.

Reviewed on Feb 23, 2026

The Orth House Inn by Remotion

The Orth House Inn by Remotion

3.5 out of 5
Price was CA $912, price is now CA $825 per person
CA $825
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Medford (MFR)
9.4/10 Exceptional! (22 reviews)
Orth house has no on-site staff, but they're text messaging worked just fine.

Reviewed on Sep 5, 2025

Where to stay in Historic Railroad District

Find the best Historic Railroad District areas and neighborhoods for the activities you enjoy most. Learn more about Historic Railroad District
Landmark building in Ashland Oregon.

Historic Downtown District

4 out of top 10 points of interest in this area
4.5/5(2 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Thomas Theatre are top sights worth seeing.

Find hotels in Historic Downtown District

Historic Railroad District Hotel Deals

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
243 4th St Ashland OR
9.6/10 Exceptional! (100 reviews)
The room was clean and the bed very comfortable. We really enjoyed relaxing in the jetted tub.

Reviewed on Feb 21, 2026

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The Peerless Hotel by WanderLodges
Premier Downstairs Flat in Perfect Down Town Location

Premier Downstairs Flat in Perfect Down Town Location

Ashland OR
10/10 Exceptional! (65 reviews)
Great location - walking distance to the Oregon Shakespeare Festival. The flat is cleaned the kitchen is stocked with more cooking utensils than I have at home. Our host made everything so comfortable. We loved our stay and will be back again.

Reviewed on Oct 17, 2025

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Premier Downstairs Flat in Perfect Down Town Location
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (2,854 reviews)
Clean room, pleasant staff. We needed parking for RV and they have a great lot for that. The breakfast is hit or miss. This time it was ok. The last time it was not. Some rooms have comfortable beds and others do not. We stay here only because of the RV parking

Reviewed on Feb 25, 2026

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Rogue Regency Inn and Suites
See all 697 properties in Historic Railroad District
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Historic Railroad District vacation package cost?
Customize your Historic Railroad District package from as low as CA $797. Choose from any combination of hotels, flights and rental cars to build the trip you've long been dreaming about. Don't forget to add on some tours and experiences!
How do I get a cheap travel package to Historic Railroad District?
Just think of all the thrilling things you could do in Historic Railroad District with a pile of extra cash in your pocket. Watch your savings stack up when you combine your flights and hotel into a Historic Railroad District vacation package. You have plenty of choice with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 hotels globally. Whether you're taking a vacation with the entire family or surprising your special someone, planning a getaway to Historic Railroad District is better with a package.
Where should I stay in Historic Railroad District?
With lots to discover in Historic Railroad District, it'd be handy for you to stay near its attractions. Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are some interesting ones to add to your to-do list.
What are the top hotels in Historic Railroad District?
If this will be your first visit to Historic Railroad District, lock in a room at BookStayHop - Peerless Hotel~ Guest Room 5 ~Downtown Ashland or New Downtown 3 Bedroom Upstairs Flat With Views. Both offer comfy beds and are top options with many savvy travelers.
How far in advance should I book my Historic Railroad District vacation?
Your best bet is to book early. Airlines typically advertise flights up to a year ahead of departure, and this is a fantastic opportunity to score some of the cheapest prices. Just been told you should take your vacation time in a few weeks? No problem! Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Historic Railroad District travel package include?
Expedia has everything you need to lock in Historic Railroad District getaway, but how your package is structured is totally up to you. Select from any combination of hotels, rental cars and flights. Searching for a few activities to keep you entertained? Once you've made your booking, you can add them too. No matter your budget or style, there's a package deal to suit your needs.
What should I know before booking a Historic Railroad District travel package?
A package can be easier on the bank balance than individually booking all you need for your escape. For example, combine your hotels, flights and rental cars and score impressive savings. No matter your vacation plans, you'll find a package that matches your budget.
Can I choose my airline with a Historic Railroad District Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to pick from around the globe. With such a huge range of choice, finding the ideal carrier to take you to Historic Railroad District won't be hard.
If I'm not able to travel, can I cancel my Historic Railroad District vacation package?
Don't worry if you're rethinking your Historic Railroad District vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can sometimes throw you a curveball, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in Historic Railroad District

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.