Holiday Homes in Ashland

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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

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 AU$599
includes taxes & fees
21 Jan - 22 Jan
Grandview of Ashland
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 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 AU$389
includes taxes & fees
22 Jan - 23 Jan
Barclay Klum House by WanderLodges
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 AU$387
includes taxes & fees
16 Feb - 17 Feb
Hanna's House by WanderLodges
Property grounds

Holiday Home in Ashland

The Red Dragon House
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 AU$310
includes taxes & fees
24 Jan - 25 Jan
The Red Dragon House
Exterior

Holiday Home in Jackson County

Cabin #15 at Hyatt Lake Resort
Cabin #15 at Hyatt Lake Resort
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 AU$330
includes taxes & fees
19 Jan - 20 Jan
Chateau Herb ~ Miranda Carriage House Apt
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)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is AU$639
includes taxes & fees
19 Jan - 20 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 AU$713
includes taxes & fees
21 Jan - 22 Jan
Hot tub | Sauna |Firepit |Sleeps 6!
Exterior

Holiday Home in Jackson County

Cabin #5 at Hyatt Lake Resort
The price is AU$385
includes taxes & fees
28 Jan - 29 Jan
Cabin #5 at Hyatt Lake Resort
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 AU$443
includes taxes & fees
28 Jan - 29 Jan
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
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 AU$305
includes taxes & fees
21 Jan - 22 Jan
Moody Ashland Escape: Luxe Suite, Copper Tub
Spa

Holiday Home in Historic Railroad District

Swank Suites | Step Free King
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 AU$267
includes taxes & fees
19 Jan - 20 Jan
Swank Suites | Step Free King
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 AU$531
includes taxes & fees
19 Jan - 20 Jan
Downtown Ashland House - Walk to Plaza and OSF!
Grand House | 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 AU$580
includes taxes & fees
21 Jan - 22 Jan
The Mountain Ave House by WanderLodges
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 AU$319
includes taxes & fees
25 Jan - 26 Jan
East Main Downtown Bungalow
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 AU$484
includes taxes & fees
19 Jan - 20 Jan
Gorgeous Lakeside BarnHOUSE + SAUNA!
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 AU$472
includes taxes & fees
21 Jan - 22 Jan
Charming house two blocks from downtown Ashland
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 AU$392
includes taxes & fees
5 Feb - 6 Feb
Hanna`s House | Downtown Retreat, Steps to OSF
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 AU$668
includes taxes & fees
28 Jan - 29 Jan
Artsy Downtown Historical House: Steps to Shakespeare
Fridge, microwave, oven, stovetop

Holiday Home in Ashland

Indulgent Retreat: 3 King Suites, Pool & Hot Tub
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 AU$826
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.
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Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"Excellent room! It had great coffee, very comfortable bed, very clean AND two massage chairs! The staff is extremely friendly and efficient. Shoutout to Cindy in the breakfast room!"
GARY 1-night trip
Posted 8 hours ago
Stratford Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
473
Accommodation
254 Holiday Homes
Lowest Price
AU$267
Highest Price
AU$826