Historic Railroad District Vacations

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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
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Historic Downtown District

4 out of top 10 points of interest in this area
5/5(133 area reviews)

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

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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! (95 reviews)
Very charming hotel, the common areas were cute and clean with free coffee and tea. My husband and I stayed in the anniversary sweet for two nights. We had an excellent stay! Checked in right at 4:00pm and self check in was a breeze. Our room was super spacious and very clean. The bathtubs were my ...

Reviewed on Nov 7, 2025

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The Peerless Hotel by WanderLodges
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
The price is ￥13,335 per night from Jan 13 to Jan 14
￥13,335
per night
Jan 13 - Jan 14
8.8/10 Excellent! (2,730 reviews)
Staff is very nice. Good price and location

Reviewed on Dec 27, 2025

Rogue Regency Inn and Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,627 reviews)
Breakfast and breakfast staff, pool saved the days. Front desk day staff were disappointing. Room 326 shower had been dyed with henna so it looked like a murder scene. My girls were afraid of it and wouldn’t use it even though it was just gross but not really blood. When I asked if it could be remedied ...

Reviewed on Dec 29, 2025

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Stratford Inn
See all 696 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.

Frequently asked questions

How much does a Historic Railroad District vacation 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 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

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

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.

Oregon Shakespeare Festival

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

￥5,446
per traveler
Ashland Puzzling Adventure
See all activities in Ashland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.