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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in Ashland

Terrace/patio
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Vacation Home in Ashland

10.0 out of 10, Exceptional, (31)
"Can't say enough good things about our stay here! This space is so thoughtfully hosted and arranged. We stayed for two nights in between camping stints in some national parks, and we especially appreciated the luxuriously comfortable beds and well-stocked kitchen tools as we refreshed ourselves, ate a couple of home-cooked meals, and took in the adorable downtown nearby."
United States
Katie M.
The price is SAR 537
SAR 960 total
includes taxes & fees
3 Dec - 4 Dec
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-size fridge, microwave, oven, stovetop
Barclay Klum House by WanderLodges

Vacation Home in Ashland

4.0 star property
10.0 out of 10, Exceptional, (6)
"Great ~ memorable stay. "
United States
Melissa
The price is SAR 524
SAR 1,067 total
includes taxes & fees
3 Dec - 4 Dec
Barclay Klum House by WanderLodges
Exterior
The Red Dragon House

Vacation Home in Ashland

10.0 out of 10, Exceptional, (103)
"I was very comfortable for My family and my two dogs, Mike and Mindy are very hospitable and very kind to work with. House is always clean. Always relaxing to go there. Will definitely come back"
United States
karen
The price is SAR 657
SAR 743 total
includes taxes & fees
3 Dec - 4 Dec
The Red Dragon House
Outdoor spa tub
Chateau Herb ~ Miranda Carriage House Apt

Vacation Home in Ashland

9.6 out of 10, Exceptional, (4)
"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 SAR 571
SAR 823 total
includes taxes & fees
3 Dec - 4 Dec
Chateau Herb ~ Miranda Carriage House Apt
Exterior
Cabin #15 at Hyatt Lake Resort

Vacation Home in Jackson County

The price is SAR 694
SAR 1,126 total
includes taxes & fees
16 Dec - 17 Dec
Cabin #15 at Hyatt Lake Resort
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster
Hanna's House by WanderLodges

Vacation Home in Historic Railroad District

4.0 star property
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is SAR 472
SAR 809 total
includes taxes & fees
1 Jan - 2 January 2026
Hanna's House by WanderLodges
Outdoor dining
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Vacation Home in Ashland

2.0 star property
The price is SAR 730
SAR 817 total
includes taxes & fees
16 Dec - 17 Dec
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Fridge, microwave, oven, stovetop
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Vacation Home in Ashland

10.0 out of 10, Exceptional, (2)
"This house was so lovely and convenient. It was nice to leave the truck parked in its spot and walk to shops and restaurants. The house itself was open and comfortable with plenty of room for the both of us. And of course that kitchen had everything we could have asked for."
United States
Kami C.
The price is SAR 545
SAR 1,356 total
includes taxes & fees
3 Dec - 4 Dec
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Microwave, oven, stovetop, dishwasher
East Main Downtown Bungalow

Vacation Home in Historic Railroad District

9.4 out of 10, Exceptional, (41)
"Great spot for those looking to visit for the Shakespeare festival - walking distance from everything! Really nice place to stay - felt super comfortable there. "
United States
Claire
The price is SAR 351
SAR 798 total
includes taxes & fees
3 Dec - 4 Dec
East Main Downtown Bungalow
Terrace/patio
Grandview of Ashland

Vacation Home in Ashland

3.0 star property
10.0 out of 10, Exceptional, (2)
"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 SAR 1,291
SAR 2,122 total
includes taxes & fees
3 Dec - 4 Dec
Grandview of Ashland
Outdoor dining
Swank Boutique Suites | Double Shower

Vacation Home in Historic Railroad District

10.0 out of 10, Exceptional, (2)
"Great stay. Very little traffic noise from E Main St. Comfortable room and unique double shower. A "
United States
Brent S.
The price is SAR 484
SAR 623 total
includes taxes & fees
3 Dec - 4 Dec
Swank Boutique Suites | Double Shower
Smart TV, books
Downtown Ashland House - Walk to Plaza and OSF!

Vacation Home in Ashland

9.8 out of 10, Exceptional, (43)
"Very nice house, fit our family of 6 comfortably. Perfect location!! Easy walk to the theaters and lots of grat places to eat. Would definitely stay here again."
United States
Julie O.
The price is SAR 469
SAR 1,339 total
includes taxes & fees
3 Dec - 4 Dec
Downtown Ashland House - Walk to Plaza and OSF!
Sauna
Gorgeous Lakeside HOUSE + Indoor SAUNA!

Vacation Home in Ashland

8.8 out of 10, Excellent, (5)
"This is a wonderful large house with lots of amenities and ease of use.It's proximity to Howard.Prairie lake was just what we were looking for we had a terrific time"
United States
Robert G.
The price is SAR 1,047
SAR 1,340 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Lakeside HOUSE + Indoor SAUNA!
Outdoor spa tub
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Vacation Home in Ashland

10.0 out of 10, Exceptional, (61)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is SAR 732
SAR 1,891 total
includes taxes & fees
3 Dec - 4 Dec
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Grand House | Private kitchen | Full-size fridge, microwave, oven, stovetop
The Mountain Ave House by WanderLodges

Vacation Home in Ashland

4.0 star property
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is SAR 851
SAR 1,589 total
includes taxes & fees
14 Dec - 15 Dec
The Mountain Ave House by WanderLodges
3 bedrooms, desk, iron/ironing board, travel crib
Indulgent Retreat: 3 King Suites, Pool & Hot Tub

Vacation Home in Ashland

10.0 out of 10, Exceptional, (26)
"We absolutely loved this property! Every room is special and the whole place is really nice. We spent a ton of time in the pool, it was our favorite part! If we're in Ashland again we will for wure stay here again!"
United States
Janelle M.
The price is SAR 751
SAR 2,133 total
includes taxes & fees
5 Dec - 6 Dec
Indulgent Retreat: 3 King Suites, Pool & Hot Tub
Outdoor dining
Hot tub | Sauna |Firepit |Sleeps 6!

Vacation Home in Ashland

10.0 out of 10, Exceptional, (3)
"Great home in a nice location with a wonderful view. Well-appointed and clean. "
United States
Ryan G.
The price is SAR 1,561
SAR 2,632 total
includes taxes & fees
2 Jan - 3 January 2026
Hot tub | Sauna |Firepit |Sleeps 6!
1 bedroom, WiFi, bed sheets
Moody Ashland Escape: Luxe Suite, Copper Tub

Vacation Home in Historic Railroad District

10.0 out of 10, Exceptional, (2)
"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 SAR 687
SAR 849 total
includes taxes & fees
3 Dec - 4 Dec
Moody Ashland Escape: Luxe Suite, Copper Tub
4 bedrooms, desk, iron/ironing board, travel crib
Ashland Luxury: 4 King suites, pool & hot tub

Vacation Home in Ashland

9.8 out of 10, Exceptional, (10)
"Good place for a group "
United States
Lynne H.
The price is SAR 938
SAR 2,606 total
includes taxes & fees
5 Dec - 6 Dec
Ashland Luxury: 4 King suites, pool & hot tub
Exterior
Artsy Downtown Historical House: Steps to Shakespeare

Vacation Home in Historic Railroad District

9.4 out of 10, Exceptional, (3)
"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 SAR 1,133
SAR 2,042 total
includes taxes & fees
3 Dec - 4 Dec
Artsy Downtown Historical House: Steps to Shakespeare
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"I love staying here because the decoration is so great and the food and service is phenomenal."
Roxane 1-night trip
Posted 12 hours ago
Ashland Hills Hotel & Suites