Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

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

Ashland OR
The price is NZ$1,038 per night from 22 Mar to 23 Mar
NZ$1,038
22 Mar - 23 Mar
includes taxes & fees
Stay at this family-friendly holiday home in Ashland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Allen Elizabethan Theatre and Angus ...
Opens in a new windowHistoric Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Spa Like Stay at the Award Winning Britt Bungalow in the Heart of Jacksonville

Spa Like Stay at the Award Winning Britt Bungalow in the Heart of Jacksonville

Jacksonville OR
The price is NZ$688 per night from 4 Apr to 5 Apr
NZ$688
4 Apr - 5 Apr
includes taxes & fees
Stay at this holiday home in Jacksonville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Kharmic Creations and Sarah Zigler Interpretive ...
Opens in a new windowSpa Like Stay at the Award Winning Britt Bungalow in the Heart of Jacksonville
Beautiful bungalow downtown Ashland railroad district

Beautiful bungalow downtown Ashland railroad district

Ashland OR
Stay at this holiday home in Ashland. Enjoy laundry facilities and air conditioning. Popular attractions Allen Elizabethan Theatre and Angus Bowmer Theatre are ...
Opens in a new windowBeautiful bungalow downtown Ashland railroad district
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Jacksonville Place

Jacksonville Place

Medford OR
The price is NZ$384 per night from 26 Mar to 27 Mar
NZ$384
26 Mar - 27 Mar
includes taxes & fees
Stay at this holiday home in Medford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Blackbird Statue and Fichtner-Mainwaring Park are ...
Opens in a new windowJacksonville Place
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den  Near Theaters, Downtown

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

Ashland OR
Stay at this holiday home in Ashland. Enjoy a garden, laundry facilities and patios. Popular attractions Ashland Library and Allen Elizabethan Theatre are located ...
Opens in a new windowBLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Premier Downstairs Flat in Perfect Down Town Location

Premier Downstairs Flat in Perfect Down Town Location

Ashland OR
Stay at this holiday home in Ashland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Ashland Library and Oregon Cabaret Theatre are located ...
Opens in a new windowPremier Downstairs Flat in Perfect Down Town Location
Station House Suite A

Station House Suite A

Jacksonville OR
The price is NZ$790 per night from 30 Mar to 31 Mar
NZ$790
30 Mar - 31 Mar
includes taxes & fees
Stay at this holiday home in Jacksonville. Enjoy laundry facilities, balconies and an in-room coffee maker. Popular attractions Kharmic Creations and Quady North ...
Opens in a new windowStation House Suite A
Luxury 5BR mountain-top retreat with private pool, breathtaking views, and total privacy. Sleeps 14 with spacious living areas, gourmet kitchen, and kid-friendly game space. Minutes to Jacksonville, wineries, and Ashland.

Luxury 5BR mountain-top retreat with private pool, breathtaking views, and total privacy. Sleeps 14 with spacious living areas, gourmet kitchen, and kid-friendly game space. Minutes to Jacksonville, wineries, and Ashland.

Jacksonville OR
Stay at this holiday home in Jacksonville. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Britt Ridge Trail and Britt Pavilion are located ...
Opens in a new windowLuxury 5BR mountain-top retreat with private pool, breathtaking views, and total privacy. Sleeps 14 with spacious living areas, gourmet kitchen, and kid-friendly game space. Minutes to Jacksonville, wineries, and Ashland.
Comfy Cozy Casa

Comfy Cozy Casa

Medford OR
The price is NZ$438 per night from 22 Mar to 23 Mar
NZ$438
22 Mar - 23 Mar
includes taxes & fees
Stay at this holiday home in Medford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Medford Railroad Park and Rogue Valley Mall are ...
Opens in a new windowComfy Cozy Casa
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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
254 Holiday Homes
Lowest Price
NZ$201
Highest Price
NZ$1,038
Popular accommodation
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly, Spa Like Stay at the Award Winning Britt Bungalow in the Heart of Jacksonville, Beautiful bungalow downtown Ashland railroad district, Jacksonville Place, BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown, Premier Downstairs Flat in Perfect Down Town Location , Station House Suite A, Luxury 5BR mountain-top retreat with private pool, breathtaking views, and total privacy. Sleeps 14 with spacious living areas, gourmet kitchen, and kid-friendly game space. Minutes to Jacksonville, wineries, and Ashland., Comfy Cozy Casa

Top trending hotels in Ashland

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$258 per night from 22 Mar to 23 Mar
NZ$258
22 Mar - 23 Mar
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the pool in their reviews. Popular ...
Opens in a new windowStratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 31 Mar to 1 Apr
NZ$210
31 Mar - 1 Apr
includes taxes & fees
Stay at this spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowAshland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
Opens in a new windowAshland Hills Hotel & Suites
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Lithia Springs Resort

Lithia Springs Resort

3 out of 5
2165 W Jackson Rd Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 31 Mar to 1 Apr
NZ$201
31 Mar - 1 Apr
includes taxes & fees
Stay at this B&B in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowLithia Springs Resort
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.