Vacation Rentals in Historic Railroad District, OR: Compare 10+ Sites & Save

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  6.  Historic Railroad District

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177 Best Vacation Rentals in Historic Railroad District (Starting from $95)

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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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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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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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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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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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 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  -  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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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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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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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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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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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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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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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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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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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 | 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 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 #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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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 | 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
Check Availability
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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Abbott's Cottages- The Wren. 1 bedroom within walking distance to downtown
Abbott's Cottages- The Wren. 1 bedroom within walking distance to downtown
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Railroad District center

AC, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$95
Average price / night
Check Availability

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 Vacation Rentals in Historic Railroad District.

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Frequently Asked Questions

You can explore 177 verified vacation rentals in Historic Railroad District. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Historic Railroad District vary depending on the season, property size, and location. Rates typically start from around $95 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Historic Railroad District include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Historic Railroad District welcome pets. Currently, 33 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Historic Railroad District often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.