Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

In the historic railroad district, walking distance to all the best of Ashland!

In the historic railroad district, walking distance to all the best of Ashland!

Ashland
Stay at this vacation home in Ashland. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Ashland Library and Oregon Cabaret Theatre ...
In the historic railroad district, walking distance to all the best of Ashland!
Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown

Ashland
The price is NZ$560 per night from 17 Aug to 18 Aug
NZ$560
17 Aug - 18 Aug
includes taxes & fees
Stay at this vacation home in Ashland. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Ashland Library and Oregon Cabaret ...
Quiet and peaceful cottage close to downtown
A beautiful Skyfall Landing

A beautiful Skyfall Landing

Eagle Point
The price is NZ$639 per night from 16 Aug to 17 Aug
NZ$639
16 Aug - 17 Aug
includes taxes & fees
Book a stay at this business-friendly vacation home in Eagle Point. Enjoy free WiFi, breakfast (surcharge), and concierge services. Popular attractions Takelma ...
A beautiful Skyfall Landing
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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

Ashland
The price is NZ$1,028 per night from 1 Sept to 2 Sept
NZ$1,028
1 Sept - 2 Sept
includes taxes & fees
Book a stay at this family-friendly vacation home in Ashland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Allen Elizabethan Theatre ...
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Jacksonville Place

Jacksonville Place

Medford
The price is NZ$403 per night from 11 Aug to 12 Aug
NZ$403
11 Aug - 12 Aug
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 ...
Jacksonville Place
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 ...
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Premier Downstairs Flat in Perfect Down Town Location

Premier Downstairs Flat in Perfect Down Town Location

Ashland
Stay at this vacation home in Ashland. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Ashland Library and Oregon Cabaret Theatre ...
Premier Downstairs Flat in Perfect Down Town Location
Downtown Delight: Ashland's Walkable Retreat

Downtown Delight: Ashland's Walkable Retreat

Ashland
The price is NZ$1,142 per night from 17 Aug to 18 Aug
NZ$1,142
17 Aug - 18 Aug
includes taxes & fees
Book a stay at this family-friendly vacation home in Ashland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Allen Elizabethan Theatre ...
Downtown Delight: Ashland's Walkable Retreat
East Main Downtown Bungalow

East Main Downtown Bungalow

Ashland
The price is NZ$506 per night from 18 Aug to 19 Aug
NZ$506
18 Aug - 19 Aug
includes taxes & fees
Stay at this vacation home in Ashland. Enjoy laundry facilities, in-room washers/dryers, and air conditioning. Popular attractions Ashland Library and Oregon ...
East Main Downtown Bungalow
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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
303 Holiday Homes
Lowest Price
NZ$164
Highest Price
NZ$1,142
Popular accommodation
In the historic railroad district, walking distance to all the best of Ashland!, Quiet and peaceful cottage close to downtown, A beautiful Skyfall Landing, Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly, Jacksonville Place, BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown, Premier Downstairs Flat in Perfect Down Town Location , Downtown Delight: Ashland's Walkable Retreat, East Main Downtown Bungalow

Top trending hotels in 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$279 per night from 17 Aug to 18 Aug
NZ$279
17 Aug - 18 Aug
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 ...
Ashland Hills Hotel & Suites
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 1 Sept to 2 Sept
NZ$164
1 Sept - 2 Sept
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 ...
Comfort Inn & Suites 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
The price is NZ$167 per night from 4 Aug to 5 Aug
NZ$167
4 Aug - 5 Aug
includes taxes & fees
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 ...
Flagship Inn of Ashland
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The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$300 per night from 17 Aug to 18 Aug
NZ$300
17 Aug - 18 Aug
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
The Bard's Inn, BW Signature Collection by Best Western
Don't see what you're looking for?
See all available properties in 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.