A deer on a road with vegetation on the sides.

Search Holiday Homes in Ashland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Ashland holiday homes

Smart TV

1. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (51 reviews)
"Enjoyed our stay. Convenient to downtown shops. Clean, comfortable and well stocked with utensils and cooking equipment. Bed was comfortable. "
United States
Hope S.
The price is £163
includes taxes & fees
31 Aug - 1 Sept
East Main Downtown Bungalow
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, free WiFi

2. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is £225
includes taxes & fees
25 Aug - 26 Aug
Barclay Klum House by WanderLodges
Interior detail

3. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
The price is £197
includes taxes & fees
7 Sept - 8 Sept
Hanna's House by WanderLodges
Interior

4. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is £350
includes taxes & fees
11 Sept - 12 Sept
Savage Upon Siskiyou
Grand House | Living area | 65-inch TV with digital channels, streaming services

5. 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 £291
includes taxes & fees
16 Aug - 17 Aug
The Mountain Ave House by WanderLodges
Sun deck

6. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (8 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 £335
includes taxes & fees
26 Aug - 27 Aug
Grandview of Ashland
Smart TV

7. 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 £225
includes taxes & fees
7 Sept - 8 Sept
Hanna`s House | Downtown Retreat, Steps to OSF
Exterior

8. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
The price is £171
includes taxes & fees
19 Aug - 20 Aug
Whimsy on B | The Studio
Exterior

9. Downtown Ashland House - Walk to Plaza and OSF!

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (46 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
The price is £286
includes taxes & fees
24 Aug - 25 Aug
Downtown Ashland House - Walk to Plaza and OSF!
Outdoor dining

10. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
9.8 out of 10, Exceptional, (8 reviews)
"Excellent…well thought out, attention to detail, comfortable, clean and friendly staff!Would definitely stay here again!"
United States
Susie P.
Swank Suites | King with Lux Tub
Coffee/tea maker, fridge, microwave, oven

11. 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
9.8 out of 10, Exceptional, (75 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is £361
includes taxes & fees
17 Aug - 18 Aug
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Coffee/tea maker, fridge, microwave, oven

12. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (69 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.
The price is £248
includes taxes & fees
17 Aug - 18 Aug
Quiet and peaceful cottage close to downtown
Exterior

13. Chateau Herb ~ Juliet Carriage House Studio

Chateau Herb ~ Juliet Carriage House Studio
Ashland
8.8 out of 10, Excellent, (8 reviews)
"Beautiful property, room very clean and well-appointed. "
United States
Anonymous traveller
Chateau Herb ~ Juliet Carriage House Studio
Smart TV

14. 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 £310
includes taxes & fees
30 Aug - 31 Aug
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Interior

15. The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (35 reviews)
"Gorgeous place! Especially enjoyed the pool and hot tub! Very comfy, quiet, and we loved the location. "
United States
Pretty W.
The Ashland Social | Main House
1 bedroom, WiFi, bed sheets

16. Moody Ashland Escape: Luxe Suite, Copper Tub

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (3 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 £229
includes taxes & fees
1 Sept - 2 Sept
Moody Ashland Escape: Luxe Suite, Copper Tub
Property grounds

17. Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.6 out of 10, Exceptional, (12 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.
The price is £292
includes taxes & fees
16 Aug - 17 Aug
Charming house two blocks from downtown Ashland
Exterior

18. Savage Upon Siskiyou | Prime OSF Location

Savage Upon Siskiyou | Prime OSF Location
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (1 review)
"We loved the charm and character of this historic home! Very beautifully updated inside, my mother and daughter and I enjoyed a fun weekend in Ashland. The home was within a nice walking distance of downtown, perfect for shopping, eating out and theater going. We will definitely look to stay here again!"
United States
Jill A.
The price is £328
includes taxes & fees
9 Sept - 10 Sept
Savage Upon Siskiyou | Prime OSF Location
Exterior

19. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
Whimsy on B | 2BR Steps to Downtown
Outdoor dining

20. 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.
The price is £497
includes taxes & fees
13 Sept - 14 Sept
Hot tub | Sauna |Firepit |Sleeps 6!
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

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"Breakfast was great! Had ample room for parking my big truck and trailer. Nice room, will stay again when in the area."
Bernard 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Ashland

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
515
Accommodation
291 Holiday Homes
Lowest Price
£163
Highest Price
£497