Short-Term Rentals in Historic Railroad District, OR: Compare 10+ Sites & Save

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175 Best Short-Term Rentals in Historic Railroad District (Starting from $117)

Swank House on Main St in Ashland
Swank House on Main St in Ashland
House
Ashland, OR, USA
0.2k from Historic Railroad District center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$527
Average price / night
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Alley-By Loft: Smack Dab in the Middle of Ashland!  Steps from Theaters & Lithia
Alley-By Loft: Smack Dab in the Middle of Ashland! Steps from Theaters & Lithia
Condo
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms10 Guests
9.4

Superb

3 reviews

$613
Average price / night
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Hanna's House by WanderLodges
Hanna's House by WanderLodges
House
Ashland, OR, USA
0.2k from Historic Railroad District center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Onsen, Lodgings, Places to stay

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$197
Average price / night
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ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown
ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown
Cottage
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$287
Average price / night
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Second Street Cottages
Second Street Cottages
House
Ashland, OR, USA
0.2k from Historic Railroad District center

Accessibility, Balcony/Terrace, Entertainment, Skiing, Parking, Transportation/Shuttle, Bar

5 Bedrooms10 Guests
9.8

Exceptional

44 reviews

$117
Average price / night
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Lodging and Art Gallery-Charming Space Next to Everything, Walk Anywhere!
Lodging and Art Gallery-Charming Space Next to Everything, Walk Anywhere!
House
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

44 reviews

$273
Average price / night
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The Matriarch Suites- Downtown Ashland, OR
The Matriarch Suites- Downtown Ashland, OR
House
Ashland, OR, USA
0.3k from Historic Railroad District center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.2

Superb

43 reviews

$235
Average price / night
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BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
House
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
9.6

Exceptional

75 reviews

$496
Average price / night
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The Matriarch Heritage House- Downtown Ashland
The Matriarch Heritage House- Downtown Ashland
House
Ashland, OR, USA
0.3k from Historic Railroad District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
8.0

Good

1 reviews

$383
Average price / night
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BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
House
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.6

Exceptional

89 reviews

$412
Average price / night
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Redtail Inn - 3 Suites Sleeps Up To 12
Redtail Inn - 3 Suites Sleeps Up To 12
House
Ashland, OR, USA
0.3k from Historic Railroad District center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

8 Bedrooms24 Guests
9.8

Exceptional

10 reviews

$398
Average price / night
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20% off OSF tix in B&C sections for guests! 5-min walk to downtwn, private yard
20% off OSF tix in B&C sections for guests! 5-min walk to downtwn, private yard
Cottage
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Elevator, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom3 Guests
9.8

Exceptional

48 reviews

$182
Average price / night
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Bluemoon Vacation Rentals - Anne Hathaway House
Bluemoon Vacation Rentals - Anne Hathaway House
House
Ashland, OR, USA
0.3k from Historic Railroad District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$703
Average price / night
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232-Duplex-Private Bathroom-Mountain View
232-Duplex-Private Bathroom-Mountain View
House
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

46 reviews

$399
Average price / night
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Mahar Homes - Plaza North on First
Mahar Homes - Plaza North on First
Apartment
Ashland, OR, USA
0.3k from Historic Railroad District center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

7 Bedrooms22 Guests
9.7

Exceptional

3 reviews

$365
Average price / night
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230-Downstairs-Duplex-Private Bathroom-Mountain View
230-Downstairs-Duplex-Private Bathroom-Mountain View
House
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

23 reviews

$399
Average price / night
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Cozy Modern Cottage
Cozy Modern Cottage
House
Ashland, OR, USA
0.3k from Historic Railroad District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$247
Average price / night
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The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Fireplace, Free Parking, Heater, Internet, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$230
Average price / night
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Pioneer Vacation Rentals - Pioneer Craftsman House
Pioneer Vacation Rentals - Pioneer Craftsman House
House
Ashland, OR, USA
0.4k from Historic Railroad District center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$374
Average price / night
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The Peerless Hotel | Junior Suite #5 | Jetted Tub
The Peerless Hotel | Junior Suite #5 | Jetted Tub
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Fireplace, Free Parking, Heater, Internet, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$230
Average price / night
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Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland
Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland
House
Ashland, OR, USA
0.5k from Historic Railroad District center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$351
Average price / night
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The Peerless Hotel | Junior Suite #2 | Jetted Tub
The Peerless Hotel | Junior Suite #2 | Jetted Tub
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Fireplace, Free Parking, Heater, Internet, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$230
Average price / night
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The Peerless Hotel | Signature Room #6 | Clawfoot Tub
The Peerless Hotel | Signature Room #6 | Clawfoot Tub
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Fireplace, Free Parking, Heater, Internet, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$216
Average price / night
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The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs
The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Fireplace, Free Parking, Heater, Internet, Living Area, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$273
Average price / night
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The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views
The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Railroad District center

AC, Balcony, Fireplace, Free Parking, Heater, Internet, Living Area, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$273
Average price / night
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Hanna`s House | Downtown Retreat, Steps to OSF
Hanna`s House | Downtown Retreat, Steps to OSF
House
Ashland, OR, 97520, United States
0.2k from Historic Railroad District center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

170 reviews

$401
Average price / night
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Swank House -Downtown Suite- Pet Friendly
Swank House -Downtown Suite- Pet Friendly
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Railroad District center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Laundry

10.0

Exceptional

5 reviews

$170
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Historic Railroad District.

Stay Near Historic Railroad District's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Historic Railroad District Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 175 verified short-term rentals in Historic Railroad District, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Historic Railroad District vary depending on location, property size, and travel dates. Rates typically start from around $117 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Historic Railroad District include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Historic Railroad District, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Historic Railroad District often include amenities such as Fireplace/Heating, Internet, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Historic Railroad District are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.