Historic Railroad District Holidays

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Your Historic Railroad District Holiday

Immerse yourself in the best that Historic Railroad District offers with a Historic Railroad District holiday package. From its history to every other thing that makes it special, this neighbourhood will delight you from start to finish. Not sure what to do and see during your trip to Historic Railroad District? Nearby attractions such as Southern Oregon University, Oregon Shakespeare Festival and Lithia Park are good places to start. Whatever your travel goals or the size of your budget, booking the ultimate Historic Railroad District holiday has never been easier with Expedia.

Our guide on 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

5 out of top 10 points of interest in this area

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Thomas Theatre.

Find hotels in Historic Downtown District

Our pick of the best 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! (99 reviews)
This historic hotel was everything we hoped for. Was very low key in a quiet neighborhood. The twin soaking tubs were perfect. It really felt like a trip back in time. We will definitely be back!

Reviewed on 22 Jan 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
9.8/10 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 17 Oct 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! (2,850 reviews)
yes room was clean and big

Reviewed on 22 Feb 2026

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Rogue Regency Inn and Suites
See all 698 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.
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Frequently asked questions

How much does a Historic Railroad District holiday package cost?
Customize your Historic Railroad District package from as low as . 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 holiday 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 holiday 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 travellers.
How far in advance should I book my Historic Railroad District holiday?
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 holiday 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 holiday plans, you'll find a package that matches your budget.
Can I choose my airline with a Historic Railroad District Expedia holiday 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 holiday package?
Don't worry if you're rethinking your Historic Railroad District holiday 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

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 get tickets for a performance 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
USA, Oregon, Mt Ashland. Fresh snow on evergreens.

Mount Ashland Ski Area

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

Mount Ashland Ski Area

ScienceWorks Hands-On Museum

You can spend time browsing the exhibits at ScienceWorks Hands-On Museum in Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.

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