Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

Jacksonville Place

Jacksonville Place

Medford
The price is NZ$318 per night from 22 Sept to 23 Sept
NZ$318
22 Sept - 23 Sept
includes taxes & fees
Stay at this vacation home in Medford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Blackbird Statue and Fichtner-Mainwaring Park are ...
Opens in a new windowJacksonville Place
Jacksonville Mountain Retreat

Jacksonville Mountain Retreat

Jacksonville
Stay at this vacation home in Jacksonville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Britt Ridge Trail and Britt Pavilion are located ...
Opens in a new windowJacksonville Mountain Retreat
The Red Dragon House

The Red Dragon House

Ashland
The price is NZ$338 per night from 21 Sept to 22 Sept
NZ$338
21 Sept - 22 Sept
includes taxes & fees
Stay at this vacation home in Ashland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Weisinger Family Winery and Emigrant Lake are located ...
Opens in a new windowThe Red Dragon House
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Small house perfect for families and pets

Small house perfect for families and pets

Medford
The price is NZ$397 per night from 21 Sept to 22 Sept
NZ$397
21 Sept - 22 Sept
includes taxes & fees
Stay at this vacation home in Medford. Popular attractions Rocky Knoll Tasting Room and Cinemark Tinseltown Medford 15 are located nearby.
Opens in a new windowSmall house perfect for families and pets
3 bedrooms with king beds, 2 1/2 bathrooms.  2146 sq ft house in east Medford.

3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.

Medford
Stay at this vacation home in Medford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Roxy Ann Peak and Prescott Park and RoxyAnn Winery ...
Opens in a new window3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views

Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views

Klamath Falls
Book a stay at this ski vacation home in Klamath Falls. Enjoy a garden, laundry facilities, and ski-in/ski-out access. Popular attraction Crater Lake Zipline ...
Opens in a new windowHarriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt

Ashland
The price is NZ$445 per night from 1 Oct to 2 Oct
NZ$445
1 Oct - 2 Oct
includes taxes & fees
Stay at this vacation home in Ashland. Enjoy a sauna, a garden, and laundry facilities. Popular attractions North Mountain Park and Allen Elizabethan Theatre ...
Opens in a new windowChateau Herb ~ Miranda Carriage House Apt
Pet & family friendly 3bd house, central location, fenced yard.

Pet & family friendly 3bd house, central location, fenced yard.

Medford
Stay at this vacation home in Medford. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Rogue Valley Mall and Cinemark ...
Opens in a new windowPet & family friendly 3bd house, central location, fenced yard.
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Ashland
Stay at this vacation home in Ashland. Enjoy a garden, laundry facilities, and patios. Popular attractions Ashland Library and Allen Elizabethan Theatre are ...
Opens in a new windowBLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Ashland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Ashland vacation homes are the perfect way for you to wing it.

Holiday houses in Ashland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Ashland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Ashland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Ashland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Ashland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Ashland Holiday Homes essential information

Accommodation
301 Holiday Homes
Lowest Price
NZ$164
Highest Price
NZ$445
Popular accommodation
Jacksonville Place, Jacksonville Mountain Retreat, The Red Dragon House, Small house perfect for families and pets, 3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford., Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views, Chateau Herb ~ Miranda Carriage House Apt, Pet & family friendly 3bd house, central location, fenced yard., BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Top trending hotels in Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Opens in a new windowFlagship Inn of Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$238 per night from 28 Sept to 29 Sept
NZ$238
28 Sept - 29 Sept
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowAshland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$253 per night from 28 Sept to 29 Sept
NZ$253
28 Sept - 29 Sept
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
Opens in a new windowStratford Inn
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Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundable
The price is NZ$164 per night from 19 Oct to 20 Oct
NZ$164
19 Oct - 20 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowComfort Inn & Suites Ashland
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.