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

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176 Best Short-Term Rentals in Historic Downtown District (Starting from $78)

Mahar Homes - Plaza North on First
Mahar Homes - Plaza North on First
Apartment
Ashland, OR, USA
0.1k from Historic Downtown 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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Charming 2-bedroom Victorian Gem - Across Beautiful Lithia Park & Ashland Plaza
Charming 2-bedroom Victorian Gem - Across Beautiful Lithia Park & Ashland Plaza
House
Ashland, OR, 97520, United States
0.1k from Historic Downtown District center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Patio, Washer

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$115
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
0.1k from Historic Downtown 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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5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
Apartment
Ashland, OR, 97520, United States
0.1k from Historic Downtown District center

AC, Heater, Kitchen, Microwave, No Smoking

5 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$914
Average price / night
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Pioneer Vacation Rentals - Pioneer South downtown Ashland
Pioneer Vacation Rentals - Pioneer South downtown Ashland
House
Ashland, OR, USA
0.1k from Historic Downtown District center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$126
Average price / night
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The Matriarch| Suite 3 | Pet friendly
The Matriarch| Suite 3 | Pet friendly
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Barbecue, Free Parking, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.0

Fabulous

4 reviews

$205
Average price / night
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Pioneer Vacation Rentals - Pioneer Craftsman House
Pioneer Vacation Rentals - Pioneer Craftsman House
House
Ashland, OR, USA
0.1k from Historic Downtown 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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Affordable Luxury- One block to Downtown
Affordable Luxury- One block to Downtown
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$206
Average price / night
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The Matriarch Suites- Downtown Ashland, OR
The Matriarch Suites- Downtown Ashland, OR
House
Ashland, OR, USA
0.2k from Historic Downtown 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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Moody Ashland Escape: Luxe Suite, Copper Tub
Moody Ashland Escape: Luxe Suite, Copper Tub
House
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Balcony, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$226
Average price / night
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The Matriarch Heritage House- Downtown Ashland
The Matriarch Heritage House- Downtown Ashland
House
Ashland, OR, USA
0.2k from Historic Downtown 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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Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

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

1 Bedroom3 Guests
10.0

Exceptional

121 reviews

$199
Average price / night
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Second Street Cottages
Second Street Cottages
House
Ashland, OR, USA
0.3k from Historic Downtown 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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Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

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

1 Bedroom3 Guests
10.0

Exceptional

82 reviews

$324
Average price / night
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Hanna's House by WanderLodges
Hanna's House by WanderLodges
House
Ashland, OR, USA
0.4k from Historic Downtown 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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Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$78
Average price / night
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Swank House on Main St in Ashland
Swank House on Main St in Ashland
House
Ashland, OR, USA
0.5k from Historic Downtown 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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2BR Ashland Retreat: Steps to Shakespeare
2BR Ashland Retreat: Steps to Shakespeare
House
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

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

2 Bedrooms4 Guests
9.4

Superb

3 reviews

$498
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
0.5k from Historic Downtown 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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2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Balcony, Dryer, Kitchen, Living Area, Microwave, No Smoking, Patio, TV

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$540
Average price / night
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Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Internet, Kitchen, Microwave, No Smoking, TV

8 Bedrooms22 Guests
New to Booking
$1224
Average price / night
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3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Microwave, No Smoking, TV

3 Bedrooms8 Guests
New to Booking
$465
Average price / night
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Spacious 2 bedroom historic home with two king beds and kitchenette.
Spacious 2 bedroom historic home with two king beds and kitchenette.
Apartment
Ashland, OR, 97520, United States
0.2k from Historic Downtown District center

AC, Heater, Microwave, No Smoking, Patio, TV

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$399
Average price / night
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Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Apartment
Ashland, OR, 97520, United States
0.3k from Historic Downtown District center

AC, Balcony, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

40 reviews

$233
Average price / night
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Railroad District, steps to downtown, everything you need to enjoy Ashland!
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Cottage
Ashland, OR, 97520, United States
0.3k from Historic Downtown District center

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

2 Bedrooms5 Guests
New to Booking
$429
Average price / night
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The Victorian Secret - Just Steps to Theaters, Plaza, Restaurants & Park. ENJOY!
The Victorian Secret - Just Steps to Theaters, Plaza, Restaurants & Park. ENJOY!
House
Ashland, OR, 97520, United States
0.3k from Historic Downtown District center

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

2 Bedrooms8 Guests
10.0

Exceptional

88 reviews

$440
Average price / night
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1907 Charmer, Perfect Downtown Location, So Clean!
1907 Charmer, Perfect Downtown Location, So Clean!
House
Ashland, OR, 97520, United States
0.3k from Historic Downtown District center

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

3 Bedrooms8 Guests
9.4

Superb

126 reviews

$504
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 Downtown District.

Stay Near Historic Downtown 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 Downtown District Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 176 verified short-term rentals in Historic Downtown District, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Historic Downtown District vary depending on location, property size, and travel dates. Rates typically start from around $78 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Historic Downtown 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 Downtown 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 Downtown District often include amenities such as Fireplace/Heating, Balcony/Terrace, and Kitchen, providing a comfortable and convenient stay.

Short-term rentals in Historic Downtown 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.