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
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Ashland vacation homes

Sundeck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 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 AED 750
AED 1,466 total
includes taxes & fees
20 May - 21 May
Grandview of Ashland
Property grounds

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (108 reviews)
"Fun place, great theme, easy place to stay!"
United States
Garrett P.
The price is AED 657
AED 761 total
includes taxes & fees
19 May - 20 May
The Red Dragon House
Exterior

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (7 reviews)
"Perfect huge Chateau territory! Clean rooms) quiet territory. The hosts are always available. "
United States
Irina
The price is AED 658
AED 917 total
includes taxes & fees
20 May - 21 May
Chateau Herb ~ Miranda Carriage House Apt
Exterior

Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort
Jackson County
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 AED 566
AED 962 total
includes taxes & fees
19 May - 20 May
Cabin #4 at Hyatt Lake Resort
Grand House | Living area | 65-inch TV with digital channels, streaming services

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)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is AED 598
AED 1,236 total
includes taxes & fees
20 May - 21 May
The Mountain Ave House by WanderLodges
Exterior

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.4 out of 10, Exceptional, (8 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 AED 922
AED 1,190 total
includes taxes & fees
19 May - 20 May
Gorgeous Lakeside BarnHOUSE + SAUNA!
Outdoor dining

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning property in the hills of Ashland!"
United States
Heather K.
Hot tub | Sauna |Firepit |Sleeps 6!
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 AED 405
AED 734 total
includes taxes & fees
25 May - 26 May
Hanna's House by WanderLodges
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, free WiFi

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is AED 538
AED 1,088 total
includes taxes & fees
20 May - 21 May
Barclay Klum House by WanderLodges
Exterior

Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort
Jackson County
The price is AED 643
AED 1,053 total
includes taxes & fees
19 May - 20 May
Cabin #5 at Hyatt Lake Resort
Exterior

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Ashland
7.0 out of 10, Good, (2 reviews)
"Very cute little spot, feels very private. The host is very friendly and helpful. "
United States
Jacob E.
The price is AED 734
AED 816 total
includes taxes & fees
20 May - 21 May
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
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, (5 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 AED 602
AED 1,301 total
includes taxes & fees
20 May - 21 May
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Property grounds

Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (66 reviews)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
Quiet and peaceful cottage close to downtown
Smart TV

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (46 reviews)
"Len and Amber were wonderful hosts!They were very responsive to my inquiries and went above and beyond to make us feel welcome. They were open to my suggestion to add night lights and genuinely showed how making their guests feel welcome and comfortable a top priority. We will be back!Beautiful home, great parking, close to everything!"
United States
shelly B.
The price is AED 362
AED 793 total
includes taxes & fees
25 May - 26 May
East Main Downtown Bungalow
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)
"Charming as can be and at the perfect location for all that Ashland has to offer. The neighborhood is quiet and friendly with lots to offer."
United States
Bill B.
Charming house two blocks from downtown Ashland
Spa

Swank Suites | Step Free King

Swank Suites | Step Free King
Historic Railroad District
8.8 out of 10, Excellent, (3 reviews)
"Cute property with a great location to downtown, we we were able to walk there."
United States
Julie S.
Swank Suites | Step Free King
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, (66 reviews)
"Great location and wonderful hot tub!"
United States
Ruth R.
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Outdoor dining

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is AED 841
AED 1,548 total
includes taxes & fees
19 May - 20 May
Savage Upon Siskiyou
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.
Hanna`s House | Downtown Retreat, Steps to OSF
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.
Moody Ashland Escape: Luxe Suite, Copper 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

Stratford Inn

Stratford Inn

10/10 Excellent
"This is a wonderful, older hotel in very close walking distance to downtown Ashland. There is a saltwater pool and hot tub that were great. Right across the street from a Safeway store which was super handy. We parked our car and didn't use it for 3 days--just walked everywhere in town, to Shakespeare festival, to fabulous meals, etc. The breakfast leaves a bit to be desired, but oatmeal and granola kept us going until lunch. The staff is all really friendly. New paint throughout and great beds!!"
Suanne 3-night trip
Posted 2 hours ago
Stratford Inn

Explore a world of travel with Expedia