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

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42 Best Family Vacation Rentals in Skidmore Academy Historic District (Starting from $117)

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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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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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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Downtown Ashland House - Walk to Plaza and OSF!
Downtown Ashland House - Walk to Plaza and OSF!
House
Ashland, OR, 97520, United States
1.1k from Skidmore Academy Historic District center

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

2 Bedrooms8 Guests
9.8

Exceptional

45 reviews

$356
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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House + 2 Studios- 3 blocks from the Plaza!
House + 2 Studios- 3 blocks from the Plaza!
House
Ashland, OR, 97520, United States
1.1k from Skidmore Academy Historic District center

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

4 Bedrooms16 Guests
9.8

Exceptional

18 reviews

$594
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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Downtown Ashland Studio - 3 blocks from the plaza!
Downtown Ashland Studio - 3 blocks from the plaza!
Apartment
Ashland, OR, 97520, United States
1.1k from Skidmore Academy Historic District center

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

1 Bedroom4 Guests
9.4

Superb

23 reviews

$212
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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Quaint Downtown Ashland Studio- pet friendly!
Quaint Downtown Ashland Studio- pet friendly!
Apartment
Ashland, OR, 97520, United States
1.1k from Skidmore Academy Historic District center

AC, Crib, Extra Bed, Internet, Kitchen, Living Area, Microwave, No Smoking, Toys

1 Bedroom4 Guests
9.2

Superb

13 reviews

$210
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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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
1.7k from Skidmore Academy Historic 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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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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Charming house two blocks from downtown Ashland
Charming house two blocks from downtown Ashland
House
Ashland, OR, 97520, United States
2.0k from Skidmore Academy Historic District center

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

2 Bedrooms4 Guests
9.4

Superb

10 reviews

$419
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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The Ashland Cottage, walk to town
The Ashland Cottage, walk to town
Cottage
Ashland, OR, 97520, United States
2.0k from Skidmore Academy Historic District center

AC, Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom4 Guests
10.0

Exceptional

218 reviews

$210
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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Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.
Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.
Apartment
Ashland, OR, 97520, United States
2.0k from Skidmore Academy Historic District center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

4 Bedrooms12 Guests
9.4

Superb

3 reviews

$1049
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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Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
House
Ashland, OR, 97520, United States
2.4k from Skidmore Academy Historic District center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$275
Average price / night
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The Ashland Social | Main House
The Ashland Social | Main House
House
Ashland, OR, 97520, United States
2.9k from Skidmore Academy Historic District center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking

3 Bedrooms10 Guests
10.0

Exceptional

29 reviews

$675
Average price / night
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The Ashland Social | Guest Studio
The Ashland Social | Guest Studio
Apartment
Ashland, OR, 97520, United States
2.9k from Skidmore Academy Historic District center

AC, Crib, Free Parking, Heater, Internet, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
10.0

Exceptional

25 reviews

$201
Average price / night
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The Ashland Social | Entire Estate
The Ashland Social | Entire Estate
House
Ashland, OR, 97520, United States
2.9k from Skidmore Academy Historic District center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking

4 Bedrooms12 Guests
10.0

Exceptional

12 reviews

$845
Average price / night
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Cozy European Cottage 2 bd + 1 bath
Cozy European Cottage 2 bd + 1 bath
Cabin
ADU Ashland, OR, 97520, United States
3.1k from Skidmore Academy Historic District center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms3 Guests
New to Booking
$168
Average price / night
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Charming Lovely 1940s Bungalow
Charming Lovely 1940s Bungalow
House
Ashland, OR, 97520, United States
4.6k from Skidmore Academy Historic District center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$302
Average price / night
Check Availability
Home Sweet Home - Relax w/  Beautiful Big Yard and Steam Shower
Home Sweet Home - Relax w/ Beautiful Big Yard and Steam Shower
House
Ashland, OR, 97520, United States
4.9k from Skidmore Academy Historic District center

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

3 Bedrooms8 Guests
8.0

Good

1 reviews

$285
Average price / night
Check Availability
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Villa
Ashland, OR, 97520, United States
5.2k from Skidmore Academy Historic District center

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

3 Bedrooms7 Guests
10.0

Exceptional

50 reviews

$328
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 Family Vacation Rentals in Skidmore Academy Historic District.

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Skidmore Academy Historic District Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 42 verified family-friendly vacation rentals in Skidmore Academy Historic District. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Skidmore Academy Historic District vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $117 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Skidmore Academy Historic District offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Skidmore Academy Historic District are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Skidmore Academy Historic District often include amenities such as Child Friendly, Fireplace/Heating, and Balcony/Terrace. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.