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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Ashland vacation homes

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

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

Ashland
10.0 out of 10, Exceptional, (31)
"Our stay was amazing everything"
United States
annie t.
The price is AED 526
AED 940 total
includes taxes & fees
10 Dec - 11 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

Barclay Klum House by WanderLodges

4.0 star property
Ashland
10.0 out of 10, Exceptional, (6)
"Great ~ memorable stay. "
United States
Melissa
The price is AED 426
AED 941 total
includes taxes & fees
1 Jan - 2 January 2026
Barclay Klum House by WanderLodges
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster
Hanna's House by WanderLodges

Hanna's House by WanderLodges

4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is AED 416
AED 738 total
includes taxes & fees
3 Jan - 4 January 2026
Hanna's House by WanderLodges
Exterior
The Red Dragon House

The Red Dragon House

Ashland
10.0 out of 10, Exceptional, (103)
"Wonderful stay, thank you!!! Our doggo felt so at home!"
United States
Kirsten P.
The price is AED 643
AED 738 total
includes taxes & fees
10 Dec - 11 Dec
The Red Dragon House
Terrace/patio
Grandview of Ashland

Grandview of Ashland

3.0 star property
Ashland
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 AED 718
AED 1,495 total
includes taxes & fees
5 Jan - 6 January 2026
Grandview of Ashland
Outdoor spa tub
Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt

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 AED 621
AED 861 total
includes taxes & fees
7 Jan - 8 January 2026
Chateau Herb ~ Miranda Carriage House Apt
Grand House | Private kitchen | Full-size fridge, microwave, oven, stovetop
The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges

4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is AED 544
AED 1,214 total
includes taxes & fees
17 Dec - 18 Dec
The Mountain Ave House by WanderLodges
Outdoor dining
Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort

Jackson County
10.0 out of 10, Exceptional, (1)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
The price is AED 533
AED 916 total
includes taxes & fees
10 Dec - 11 Dec
Cabin #4 at Hyatt Lake Resort
Fridge, microwave, oven, stovetop
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, (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 AED 481
AED 1,253 total
includes taxes & fees
1 Jan - 2 January 2026
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

2.0 star property
Ashland
The price is AED 714
AED 796 total
includes taxes & fees
10 Dec - 11 Dec
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Exterior
Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort

Jackson County
Cabin #5 at Hyatt Lake Resort
Microwave, oven, stovetop, dishwasher
East Main Downtown Bungalow

East Main Downtown Bungalow

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
East Main Downtown Bungalow
Outdoor dining
Swank Boutique Suites | Double Shower

Swank Boutique Suites | Double Shower

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 AED 459
AED 594 total
includes taxes & fees
10 Dec - 11 Dec
Swank Boutique Suites | Double Shower
Smart TV, books
Downtown Ashland House - Walk to Plaza and OSF!

Downtown Ashland House - Walk to Plaza and OSF!

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.
Downtown Ashland House - Walk to Plaza and OSF!
Sauna
Gorgeous Lakeside HOUSE + Indoor SAUNA!

Gorgeous Lakeside HOUSE + Indoor SAUNA!

Ashland
8.8 out of 10, Excellent, (5)
"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 AED 1,025
AED 1,312 total
includes taxes & fees
10 Dec - 11 Dec
Gorgeous Lakeside HOUSE + Indoor SAUNA!
Outdoor spa tub
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, (61)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is AED 716
AED 1,851 total
includes taxes & fees
10 Dec - 11 Dec
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
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)
"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.
Moody Ashland Escape: Luxe Suite, Copper Tub
Fridge, microwave, oven, stovetop
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)
"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.
Hanna`s House | Downtown Retreat, Steps to OSF
3 bedrooms, desk, iron/ironing board, travel crib
Indulgent Retreat: 3 King Suites, Pool & Hot Tub

Indulgent Retreat: 3 King Suites, Pool & Hot Tub

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.
Indulgent Retreat: 3 King Suites, Pool & Hot Tub
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)
"Well located, nice house!"
United States
Tom J.
Charming house two blocks from downtown Ashland
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 Springs Hotel

Ashland Springs Hotel

10/10 Excellent
"We enjoyed our visit immensely. The room isn’t designed for someone who wants to work from their room, but it was perfect for a vacation. The room was beautiful, the service was great, the restaurant was delicious. We were blocks from the Shakespeare festival and steps from several great restaurants and amazing shops. "
Cynthia 4-night trip
Posted 2 days ago
Ashland Springs Hotel