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

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  6.  Skidmore Academy Historic District

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178 Best Vacation Rentals in Skidmore Academy Historic District (Starting from $101)

Grandview of Ashland
Grandview of Ashland
House
Ashland, OR, USA
0.9k from Skidmore Academy Historic District center

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

1 Bedroom6 Guests
New to Booking
$498
Average price / night
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ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown
ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown
House
Ashland, OR, 97520, United States
0.4k from Skidmore Academy Historic District center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$293
Average price / night
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Ashland Bungalow downtown
Ashland Bungalow downtown
House
Ashland, OR, USA
0.9k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
9.5

Superb

2 reviews

$121
Average price / night
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Exquisite Artist's home, all summer or month to month.
Exquisite Artist's home, all summer or month to month.
House
Ashland, OR, 97520, United States
0.4k from Skidmore Academy Historic District center

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

3 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$146
Average price / night
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Bluemoon Vacation Rentals - Bluemoon House
Bluemoon Vacation Rentals - Bluemoon House
House
Ashland, OR, USA
1.1k from Skidmore Academy Historic District center

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

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$504
Average price / night
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Monthly rental offering privacy and views near Ashland Plaza.
Monthly rental offering privacy and views near Ashland Plaza.
House
Ashland, OR, 97520, United States
0.4k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
New to Booking
$160
Average price / night
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Bluemoon Vacation Rentals - Bluemoon Cottage
Bluemoon Vacation Rentals - Bluemoon Cottage
House
Ashland, OR, USA
1.1k from Skidmore Academy Historic District center

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

1 Bedroom4 Guests
9.0

Fabulous

8 reviews

$265
Average price / night
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Monthly Rental Circular House blocks to Downtown & Oregon Shakespeare Festival
Monthly Rental Circular House blocks to Downtown & Oregon Shakespeare Festival
House
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

AC, Heater, No Smoking

4 Bedrooms6 Guests
New to Booking
$182
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
1.4k from Skidmore Academy Historic 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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Charming carriage house in Ashland near downtown
Charming carriage house in Ashland near downtown
Cottage
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

1 Bedroom4 Guests
9.8

Exceptional

9 reviews

$222
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
1.4k from Skidmore Academy Historic 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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ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown
ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown
House
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$295
Average price / night
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Pioneer Vacation Rentals - Pioneer Craftsman House
Pioneer Vacation Rentals - Pioneer Craftsman House
House
Ashland, OR, USA
1.4k from Skidmore Academy Historic 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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Stroll into Ashland from Abigail's Two Bedroom Private Vacation Cottage.
Stroll into Ashland from Abigail's Two Bedroom Private Vacation Cottage.
Cottage
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
9.6

Exceptional

14 reviews

$389
Average price / night
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The Matriarch Suites- Downtown Ashland, OR
The Matriarch Suites- Downtown Ashland, OR
House
Ashland, OR, USA
1.5k from Skidmore Academy Historic 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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The Terra Cottage Inn - Ashland, Oregon
The Terra Cottage Inn - Ashland, Oregon
Cottage
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
10.0

Exceptional

72 reviews

$223
Average price / night
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The Matriarch Heritage House- Downtown Ashland
The Matriarch Heritage House- Downtown Ashland
House
Ashland, OR, USA
1.5k from Skidmore Academy Historic 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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High Street Cottage Artists' Garden Cottage Clean & Beautiful
High Street Cottage Artists' Garden Cottage Clean & Beautiful
Cottage
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
10.0

Exceptional

71 reviews

$234
Average price / night
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Mahar Homes - Plaza North on First
Mahar Homes - Plaza North on First
Apartment
Ashland, OR, USA
1.5k from Skidmore Academy Historic 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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Vacation Home in Beautiful Ashland (Ashland, OR)
Vacation Home in Beautiful Ashland (Ashland, OR)
House
Ashland, OR, 97520, United States
0.5k from Skidmore Academy Historic District center

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

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$101
Average price / night
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Second Street Cottages
Second Street Cottages
House
Ashland, OR, USA
1.6k from Skidmore Academy Historic 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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Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
House
Ashland, OR, 97520, United States
0.6k from Skidmore Academy Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

65 reviews

$541
Average price / night
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Monthly Single family house just blocks to Ashland's downtown
Monthly Single family house just blocks to Ashland's downtown
House
Ashland, OR, 97520, United States
0.6k from Skidmore Academy Historic District center

Heater, Internet, No Smoking

4 Bedrooms4 Guests
New to Booking
$165
Average price / night
Check Availability
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
Cottage
Ashland, OR, 97520, United States
0.7k from Skidmore Academy Historic District center

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

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$167
Average price / night
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Helman Street Penthouse with a View
Helman Street Penthouse with a View
House
Ashland, OR, 97520, United States
0.7k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
10.0

Exceptional

37 reviews

$436
Average price / night
Check Availability
ABBOTT'S COTTAGES- Duck cottage. 1 bedroom/1 bath, walking distance to downtown!
ABBOTT'S COTTAGES- Duck cottage. 1 bedroom/1 bath, walking distance to downtown!
Cottage
Ashland, OR, 97520, United States
0.8k from Skidmore Academy Historic District center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$170
Average price / night
Check Availability
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
Apartment
Ashland, OR, 97520, United States
0.8k from Skidmore Academy Historic District center

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

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$148
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 Skidmore Academy Historic District.

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Frequently Asked Questions

You can explore 178 verified vacation rentals in Skidmore Academy Historic 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 Skidmore Academy Historic District vary depending on the season, property size, and location. Rates typically start from around $101 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 Skidmore Academy Historic 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 Skidmore Academy Historic District welcome pets. Currently, 34 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 Skidmore Academy Historic District often include amenities such as Fireplace/Heating, Balcony/Terrace, and Internet. 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.