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
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Ashland holiday homes

Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
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
21 Jan - 22 Jan
Grandview of Ashland
Living area

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is HK$872
HK$2,007 total
includes taxes & fees
22 Jan - 23 Jan
Barclay Klum House by WanderLodges
Interior detail

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is HK$971
HK$1,683 total
includes taxes & fees
5 Feb - 6 Feb
Hanna's House by WanderLodges
Property grounds

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (104 reviews)
"The Red Dragon House was very well represented in the description. Clean and cozy with a kitchen that was well stocked for cooking or baking, We loved everything about this vacation rental!"
United States
Barbara R.
The price is HK$1,396
HK$1,575 total
includes taxes & fees
24 Jan - 25 Jan
The Red Dragon House
Exterior

Cabin #15 at Hyatt Lake Resort

Cabin #15 at Hyatt Lake Resort
Jackson County
The price is HK$1,442
HK$2,339 total
includes taxes & fees
19 Jan - 20 Jan
Cabin #15 at Hyatt Lake Resort
Exterior

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 HK$1,186
HK$1,702 total
includes taxes & fees
19 Jan - 20 Jan
Chateau Herb ~ Miranda Carriage House Apt
Fridge, microwave, oven, stovetop

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, (62 reviews)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is HK$1,131
HK$3,425 total
includes taxes & fees
19 Jan - 20 Jan
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Outdoor dining

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
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
21 Jan - 22 Jan
Hot tub | Sauna |Firepit |Sleeps 6!
Exterior

Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort
Jackson County
The price is HK$1,209
HK$2,002 total
includes taxes & fees
18 Feb - 19 Feb
Cabin #5 at Hyatt Lake Resort
Smart TV

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 HK$986
HK$2,305 total
includes taxes & fees
22 Jan - 23 Jan
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
1 bedroom, WiFi, bed sheets

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 HK$1,255
HK$1,574 total
includes taxes & fees
21 Jan - 22 Jan
Moody Ashland Escape: Luxe Suite, Copper Tub
Spa

Swank Suites | Step Free King

Swank Suites | Step Free King
Historic Railroad District
8.0 out of 10, Very good, (2 reviews)
"Cute property with a great location to downtown, we we were able to walk there."
United States
Julie S.
The price is HK$1,076
HK$1,374 total
includes taxes & fees
19 Jan - 20 Jan
Swank Suites | Step Free King
Exterior

Downtown Ashland House - Walk to Plaza and OSF!

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
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
19 Jan - 20 Jan
Downtown Ashland House - Walk to Plaza and OSF!
Living area

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 HK$1,627
HK$3,023 total
includes taxes & fees
21 Jan - 22 Jan
The Mountain Ave House by WanderLodges
Smart TV

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (43 reviews)
"Great location "
United States
Patrick D.
East Main Downtown Bungalow
Dining

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
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
19 Jan - 20 Jan
Gorgeous Lakeside BarnHOUSE + SAUNA!
Property grounds

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)
"Well located, nice house!"
United States
Tom J.
The price is HK$1,240
HK$2,426 total
includes taxes & fees
21 Jan - 22 Jan
Charming house two blocks from downtown Ashland
Smart TV

Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
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$2,087 total
includes taxes & fees
5 Feb - 6 Feb
Hanna`s House | Downtown Retreat, Steps to OSF
TV

Artsy Downtown Historical House: Steps to Shakespeare

Artsy Downtown Historical House: Steps to Shakespeare
Historic Railroad District
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
19 Jan - 20 Jan
Artsy Downtown Historical House: Steps to Shakespeare
Fridge, microwave, oven, stovetop

Indulgent Retreat: 3 King Suites, Pool & Hot Tub

Indulgent Retreat: 3 King Suites, Pool & Hot Tub
Ashland
10.0 out of 10, Exceptional, (26 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
25 Jan - 26 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

Relax Inn At Ashland

Relax Inn At Ashland

10/10 Excellent
"Check-in was quick, easy and relaxed. The room was recently renovated and was clean and comfortable. It was compact but spacious, well stocked and finely furnished. There was a coffee stand at the Mobil gas station next door, great gas prices too. Overall this hotel is great and affordable and I highly recommend the Relaxed Inn. Cheers."
Jerry 1-night trip
Posted 3 days ago
Relax Inn At Ashland

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
473
Accommodation
254 Vacation Homes
Lowest Price
HK$1,374
Highest Price
HK$4,432

Explore a world of travel with Expedia