Ashland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ashland vacation homes

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
United States
Monica
The price is CA $488
CA $742 total
includes taxes & fees
Mar 15 - Mar 16
Grandview of Ashland

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (106 reviews)
"House was definitely pet friendly. Dogs always enjoy staying there. Very relaxing place. Beds are comfortable. House is always clean excellent place to stay"
United States
karen
The price is CA $243
CA $283 total
includes taxes & fees
Mar 14 - Mar 15
The Red Dragon House

Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort
Jackson County
10.0 out of 10, Exceptional, (1 review)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
The price is CA $197
CA $339 total
includes taxes & fees
Mar 16 - Mar 17
Cabin #4 at Hyatt Lake Resort

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay, with full kitchen, and a close drive to downtown Ashland. The AC stopped and the staff were very responsive and provided."
United States
Catherine J.
The price is CA $194
CA $287 total
includes taxes & fees
Mar 14 - Mar 15
Chateau Herb ~ Miranda Carriage House Apt

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.2 out of 10, Wonderful, (7 reviews)
"House was very clean and taken care of. A beautiful destination right across the street from lake access. Went down with a group and had an excellent stay!"
United States
Hannah D.
The price is CA $341
CA $441 total
includes taxes & fees
Mar 17 - Mar 18
Gorgeous Lakeside BarnHOUSE + SAUNA!

European Style Straw Bale Retreat

European Style Straw Bale Retreat
Ashland
10.0 out of 10, Exceptional, (4 reviews)
"Our one month stay was incredible! Highly recommended. Secluded, yet very close to town. Very quiet. The hot tub was great. 5 star."
United States
Scott B.
The price is CA $189
CA $376 total
includes taxes & fees
Mar 24 - Mar 25
European Style Straw Bale Retreat

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"This place was a 10/10! Made a big breakfast for my friends. Grocery store very close. I will be returning!"
United States
Montgomery
The price is CA $325
CA $573 total
includes taxes & fees
Mar 15 - Mar 16
The Mountain Ave House by WanderLodges

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is CA $172
CA $373 total
includes taxes & fees
Mar 15 - Mar 16
Barclay Klum House by WanderLodges

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Ashland
7.0 out of 10, Good, (2 reviews)
"Very cute little spot, feels very private. The host is very friendly and helpful. "
United States
Jacob E.
The price is CA $266
CA $305 total
includes taxes & fees
Mar 13 - Mar 14
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (4 reviews)
"Great home in a nice location with a wonderful view. Well-appointed and clean. "
United States
Ryan G.
The price is CA $447
CA $831 total
includes taxes & fees
Mar 26 - Mar 27
Hot tub | Sauna |Firepit |Sleeps 6!

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
The price is CA $193
CA $438 total
includes taxes & fees
Mar 16 - Mar 17
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

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
10.0 out of 10, Exceptional, (64 reviews)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is CA $197
CA $597 total
includes taxes & fees
Mar 13 - Mar 14
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (65 reviews)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
The price is CA $170
CA $347 total
includes taxes & fees
Mar 13 - Mar 14
Quiet and peaceful cottage close to downtown

Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.4 out of 10, Exceptional, (10 reviews)
"Charming as can be and at the perfect location for all that Ashland has to offer. The neighborhood is quiet and friendly with lots to offer."
United States
Bill B.
The price is CA $325
CA $563 total
includes taxes & fees
Mar 16 - Mar 17
Charming house two blocks from downtown Ashland

Swank Suites | Step Free King

Swank Suites | Step Free King
Historic Railroad District
8.8 out of 10, Excellent, (3 reviews)
"Cute property with a great location to downtown, we we were able to walk there."
United States
Julie S.
The price is CA $219
CA $279 total
includes taxes & fees
Mar 18 - Mar 19
Swank Suites | Step Free King

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (44 reviews)
"Great location "
United States
Patrick D.
The price is CA $127
CA $292 total
includes taxes & fees
Mar 14 - Mar 15
East Main Downtown Bungalow

Moody Ashland Escape: Luxe Suite, Copper Tub

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our overnight stay. The place is centrally located, easy walking distance to downtown, and cozy. We loved the heated bathroom floors and the decor. Nice off street parking. Highly recommend. "
United States
Jon W.
The price is CA $249
CA $317 total
includes taxes & fees
Mar 13 - Mar 14
Moody Ashland Escape: Luxe Suite, Copper Tub

Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort
Jackson County
The price is CA $224
CA $375 total
includes taxes & fees
Mar 17 - Mar 18
Cabin #5 at Hyatt Lake Resort

The Main House: The Ashland Social | Main House

The Main House: The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous place! Especially enjoyed the pool and hot tub! Very comfy, quiet, and we loved the location. "
United States
Pretty W.
The price is CA $272
CA $772 total
includes taxes & fees
Mar 13 - Mar 14
The Main House: The Ashland Social | Main House

Chateau Herb ~ Juliet Carriage House Studio

Chateau Herb ~ Juliet Carriage House Studio
Ashland
9.0 out of 10, Wonderful, (7 reviews)
"Beautiful property, room very clean and well-appointed. "
United States
Anonymous traveller
The price is CA $170
CA $258 total
includes taxes & fees
Mar 15 - Mar 16
Chateau Herb ~ Juliet Carriage House Studio
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
375
Accommodation
254 Vacation Homes
Lowest Price
CA $279
Highest Price
CA $831

Explore a world of travel with Expedia