Photo by Inna Blair
Historic Railroad District vacation rentals
We found 80 vacation rentals — enter your dates for availability
Discover a selection of 31 homes, 11 apartments, and other vacation rentals in Historic Railroad District that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, including parking and a TV. No matter what you're looking for, you'll find a rental to meet everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Historic Railroad District
Showing deals for:Nov 14 - Nov 21
Image gallery for Beautiful little place. Walk to town and theaters!
1010 out of 10 rating
Exceptional
(78 reviews)
Beautiful little place. Walk to town and theaters!
Ashland, OR
10% off
Price is CA $266
CA $266
CA $2,475 total
CA $2,475 total
includes taxes & fees
Image gallery for Centrally located Historic Home with parking
8.68.6 out of 10 rating
Excellent
(7 reviews)
Centrally located Historic Home with parking
Ashland, OR
10% off
Price is CA $331
CA $331
CA $3,021 total
CA $3,021 total
includes taxes & fees
Image gallery for Charming Space Next to Everything, Walk Anywhere!
1010 out of 10 rating
Exceptional
(41 reviews)
Charming Space Next to Everything, Walk Anywhere!
Ashland, OR
5% off
Price is CA $288
CA $288
CA $2,705 total
CA $2,705 total
includes taxes & fees
Image gallery for East Main Downtown Bungalow
9.29.2 out of 10 rating
Wonderful
(32 reviews)
East Main Downtown Bungalow
Ashland, OR
20% off
Price is CA $165
CA $165
CA $1,548 total
CA $1,548 total
includes taxes & fees
Image gallery for Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
1010 out of 10 rating
Exceptional
(79 reviews)
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Ashland, OR
20% off
Price is CA $303
CA $303
CA $2,741 total
CA $2,741 total
includes taxes & fees
Image gallery for Downtown Ashland private cottage with garden patio
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Downtown Ashland private cottage with garden patio
Ashland, OR
5% off
Price is CA $202
CA $202
CA $1,859 total
CA $1,859 total
includes taxes & fees
Image gallery for Railroad District, steps to downtown, everything you need to enjoy Ashland!
1010 out of 10 rating
Exceptional
(141 reviews)
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Ashland, OR
10% off
Price is CA $429
CA $429
CA $3,961 total
CA $3,961 total
includes taxes & fees
Image gallery for New Downtown 3 Bedroom Upstairs Flat with views
9.69.6 out of 10 rating
Exceptional
(29 reviews)
New Downtown 3 Bedroom Upstairs Flat with views
Ashland, OR
20% off
Price is CA $303
CA $303
CA $2,749 total
CA $2,749 total
includes taxes & fees
Image gallery for Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
1010 out of 10 rating
Exceptional
(113 reviews)
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Ashland, OR
20% off
Price is CA $193
CA $193
CA $1,786 total
CA $1,786 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Historic Railroad District
New Downtown 3 Bedroom Upstairs Flat with views
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Beautiful little place. Walk to town and theaters!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
A Cowslip's Belle Inn
Sleeps 3 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Downtown Ashland private cottage with garden patio
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
In the historic railroad district, walking distance to all the best of Ashland!
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
Top rated rentals - Historic Railroad District
Great Place to Stay
1010 out of 10
Exceptionalexceptional
165 reviews(165 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Historic Railroad District?
In the Historic Railroad District, vacation houses are the most popular type of rental, with around 30 available throughout the area. These homes typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many also include outdoor spaces such as gardens or patios for relaxing after a day of exploring the local attractions. Additionally, there are several apartments and cottages scattered around, which offer a more compact option for those seeking a cosy retreat.
Are there any beach house rentals in Historic Railroad District?
In the Historic Railroad District of Oregon, beach house rentals are available, although the area is renowned more for its charming historic architecture than for traditional beach settings. These rentals typically feature a blend of modern amenities and rustic charm, offering fully equipped kitchens, spacious living areas, and often outdoor patios or gardens. Visitors can enjoy proximity to local attractions such as the Oregon Coast Scenic Railroad and various art galleries.
How much does it cost to rent a vacation home in Historic Railroad District?
Prices for vacation rentals in Historic Railroad District vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Historic Railroad District to more spacious homes.
Are there any discounts for Historic Railroad District vacation house rentals?
You can find great discounts on house rentals in Historic Railroad District on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Historic Railroad District vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Historic Railroad District with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Historic Railroad District?
A long-stay vacation rental in Historic Railroad District is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Historic Railroad District for a vacation rental?
The best time to visit the Historic Railroad District for a vacation rental is during the vibrant summer months of June to August. This peak season draws visitors who are keen to immerse themselves in the area's rich history and enjoy a variety of outdoor activities. With warm temperatures averaging in the mid-20s Celsius, the district becomes a lively hub, great for exploring the charming streets lined with shops, galleries, and historic sites.
July stands out as the most popular month for travellers, offering a delightful atmosphere filled with community events and local festivals. Visitors can enjoy leisurely strolls along the scenic pathways while appreciating the unique architecture that reflects the area's railway heritage.
For those seeking a more budget-friendly experience, consider planning your visit in December. While this month falls outside the high season, it presents an enchanting opportunity to witness the district adorned in vacation decorations, creating a warm and inviting ambiance. The cooler temperatures, typically hovering around 5°C, make it a great time for cosy evenings spent enjoying local dining options.
Are there any remote work vacation rentals in Historic Railroad District?
In the Historic Railroad District of Oregon, there are numerous remote work-friendly vacation rentals available—around 42 options to choose from. This vibrant area is known for its charming architecture and proximity to the town's amenities, making it an ideal location for those looking to work remotely while enjoying a special environment.
Travellers can expect properties equipped with essential amenities for remote work, including Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. Some rentals may also feature additional workspaces or laptop-friendly areas, suiting a variety of work needs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Railroad District vacation rental?
Book your Historic Railroad District vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Historic Railroad District?
In the Historic Railroad District of Oregon, visitors can experience firsthand the unique charm of this revitalised area filled with historic architecture and vibrant arts. A must-see is the Ashland Railroad Station, a beautifully restored building that serves as a reminder of the area's rich railway history. Nearby, the Oregon Shakespeare Festival attracts theatre enthusiasts from around the globe, offering a variety of performances in multiple venues throughout the district.
Can I change or cancel my Historic Railroad District home rental booking on Vrbo?
To find Historic Railroad District vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Historic Railroad District vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.