Search Vacation Homes in Ashland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Ashland holiday homes

Sun deck

Holiday Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is HK$1,677
HK$3,119 total
includes taxes & fees
28 Jan - 29 Jan
Grandview of Ashland
Living area

Holiday Home in Ashland

Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is HK$933
HK$2,075 total
includes taxes & fees
1 Feb - 2 Feb
Barclay Klum House by WanderLodges
Property grounds

Holiday Home in Ashland

The Red Dragon House
10.0 out of 10, Exceptional, (105 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 HK$1,396
HK$1,575 total
includes taxes & fees
30 Jan - 31 Jan
The Red Dragon House
Interior detail

Holiday Home in Historic Railroad District

Hanna's House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is HK$807
HK$1,499 total
includes taxes & fees
4 Feb - 5 Feb
Hanna's House by WanderLodges
Exterior

Holiday Home in Ashland

Chateau Herb ~ Miranda Carriage House Apt
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 HK$1,186
HK$1,694 total
includes taxes & fees
25 Jan - 26 Jan
Chateau Herb ~ Miranda Carriage House Apt
Exterior

Holiday Home in Jackson County

Cabin #4 at Hyatt Lake Resort
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 HK$1,131
HK$1,938 total
includes taxes & fees
23 Feb - 24 Feb
Cabin #4 at Hyatt Lake Resort
Fridge, microwave, oven, stovetop

Holiday Home in Ashland

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
10.0 out of 10, Exceptional, (62 reviews)
"The property was beautiful, clean and as advertised. Easy accessibility to the town and a nice, safe neighborhood. We had a wonderful stay, thank you!"
United States
Dave N.
The price is HK$1,131
HK$3,425 total
includes taxes & fees
25 Jan - 26 Jan
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Outdoor dining

Holiday Home in Ashland

Hot tub | Sauna |Firepit |Sleeps 6!
10.0 out of 10, Exceptional, (3 reviews)
"Great home in a nice location with a wonderful view. Well-appointed and clean. "
United States
Ryan G.
The price is HK$1,707
HK$3,745 total
includes taxes & fees
28 Jan - 29 Jan
Hot tub | Sauna |Firepit |Sleeps 6!
Smart TV

Holiday Home in Ashland

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
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 HK$986
HK$2,366 total
includes taxes & fees
27 Jan - 28 Jan
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior

Holiday Home in Ashland

Downtown Ashland House - Walk to Plaza and OSF!
9.8 out of 10, Exceptional, (44 reviews)
"Comfortable house & coveniently located a short walk to downtown Ashland's Main Street restaurants, shops & Oregon Shakespeare Festival theaters."
United States
Richard S.
The price is HK$975
HK$2,783 total
includes taxes & fees
23 Feb - 24 Feb
Downtown Ashland House - Walk to Plaza and OSF!
Outdoor dining

Holiday Home in Historic Railroad District

Swank Suites | King with Lux Tub
9.6 out of 10, Exceptional, (5 reviews)
"Excellent…well thought out, attention to detail, comfortable, clean and friendly staff!Would definitely stay here again!"
United States
Susie P.
The price is HK$1,021
HK$1,313 total
includes taxes & fees
29 Jan - 30 Jan
Swank Suites | King with Lux Tub
Exterior

Holiday Home in Jackson County

Cabin #5 at Hyatt Lake Resort
The price is HK$1,209
HK$2,026 total
includes taxes & fees
24 Feb - 25 Feb
Cabin #5 at Hyatt Lake Resort
Dining

Holiday Home in Ashland

Gorgeous Lakeside BarnHOUSE + SAUNA!
8.8 out of 10, Excellent, (5 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 HK$1,958
HK$2,533 total
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Lakeside BarnHOUSE + SAUNA!
Smart TV

Holiday Home in Historic Railroad District

East Main Downtown Bungalow
9.4 out of 10, Exceptional, (43 reviews)
"Great location "
United States
Patrick D.
The price is HK$730
HK$1,648 total
includes taxes & fees
25 Jan - 26 Jan
East Main Downtown Bungalow
Property grounds

Holiday Home in Historic Railroad District

Charming house two blocks from downtown Ashland
9.4 out of 10, Exceptional, (10 reviews)
"Well located, nice house!"
United States
Tom J.
The price is HK$1,240
HK$2,460 total
includes taxes & fees
27 Jan - 28 Jan
Charming house two blocks from downtown Ashland
TV

Holiday Home in Historic Railroad District

Artsy Downtown Historical House: Steps to Shakespeare
9.4 out of 10, Exceptional, (3 reviews)
"I've been visiting Ashland for 15 years, and The Matriarch (also known as the Swank House) is by far the best location I've ever stayed in. It's beautifully classy, incredibly comfortable, and perfectly situated—just a short walk to everything I love: the Cabaret, Lithia Park, restaurants, and shopping. I especially appreciated being able to drop off purchases or refrigerate leftovers in between outings—so convenient!The communication was seamless: clear, accommodating, and never intrusive. The...
United States
Eileen B.
The price is HK$1,676
HK$3,382 total
includes taxes & fees
25 Jan - 26 Jan
Artsy Downtown Historical House: Steps to Shakespeare
1 bedroom, WiFi, bed sheets

Holiday Home in Historic Railroad District

Moody Ashland Escape: Luxe Suite, Copper Tub
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 HK$1,255
HK$1,574 total
includes taxes & fees
25 Jan - 26 Jan
Moody Ashland Escape: Luxe Suite, Copper Tub
Smart TV

Holiday Home in Historic Railroad District

Hanna`s House | Downtown Retreat, Steps to OSF
10.0 out of 10, Exceptional, (170 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is HK$1,106
HK$2,069 total
includes taxes & fees
23 Feb - 24 Feb
Hanna`s House | Downtown Retreat, Steps to OSF
Living area

Holiday Home in Ashland

The Mountain Ave House by WanderLodges
4.0 star property
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 HK$1,627
HK$3,023 total
includes taxes & fees
1 Feb - 2 Feb
The Mountain Ave House by WanderLodges
Fridge, microwave, oven, stovetop

Holiday Home in Ashland

Indulgent Retreat: 3 King Suites, Pool & Hot Tub
10.0 out of 10, Exceptional, (27 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 HK$1,559
HK$4,432 total
includes taxes & fees
28 Jan - 29 Jan
Indulgent Retreat: 3 King Suites, Pool & Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Ashland Commons Hostel

Ashland Commons Hostel

10/10 Excellent
"Staffs are so friendly. Clean property.especially the bathroom!"
Hezekiel 3-night trip
Posted 4 days ago
Ashland Commons Hostel

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
477
Accommodation
254 Vacation Homes
Lowest Price
HK$1,313
Highest Price
HK$4,432

Explore a world of travel with Expedia