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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Ashland holiday homes

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is £207
includes taxes & fees
4 Oct - 5 Oct
Barclay Klum House by WanderLodges
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

2. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (54 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
The price is £166
includes taxes & fees
12 Oct - 13 Oct
East Main Downtown Bungalow
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

3. 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 £318
includes taxes & fees
6 Oct - 7 Oct
Savage Upon Siskiyou
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

4. 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 £207
includes taxes & fees
6 Oct - 7 Oct
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

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 £296
includes taxes & fees
4 Oct - 5 Oct
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

6. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is £309
includes taxes & fees
4 Oct - 5 Oct
Grandview of Ashland
A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

7. 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, (6 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 £249
includes taxes & fees
29 Sept - 30 Sept
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

8. 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, (83 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is £367
includes taxes & fees
29 Sept - 30 Sept
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
A garden with a white fence, green hedges, and purple flowering trees.

9. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"This is a great place to stay. Walkable to the theaters and many restaurants. Thank you!"
United States
Christy G.
The price is £191
includes taxes & fees
11 Oct - 12 Oct
Whimsy on B | The Studio
A two-story house with a porch, a wooden fence, and a paved driveway.

10. 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 £274
includes taxes & fees
30 Sept - 1 Oct
Downtown Ashland House - Walk to Plaza and OSF!
A kitchen with granite countertops, dark cabinetry, and a refrigerator.

11. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (71 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 £255
includes taxes & fees
29 Sept - 30 Sept
Quiet and peaceful cottage close to downtown
Exterior

12. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."
United States
Cameron A.
The price is £195
includes taxes & fees
29 Sept - 30 Sept
Chateau Herb ~ Miranda Carriage House Apt
A kitchen with white cabinetry, a black backsplash with star patterns, and two framed vintage Vogue magazine covers on the wall.

13. 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.
The price is £149
includes taxes & fees
5 Oct - 6 Oct
Swank Suites | King with Lux Tub
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

14. 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, (171 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 £255
includes taxes & fees
4 Oct - 5 Oct
Hanna`s House | Downtown Retreat, Steps to OSF
A bedroom with a large bed, a chandelier, a desk, a chair, and a window with curtains.

15. 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 £196
includes taxes & fees
14 Oct - 15 Oct
Moody Ashland Escape: Luxe Suite, Copper Tub
A hallway with a blue wall, a framed welcome sign, a round mirror, and a table.

16. The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (38 reviews)
"Home is beautiful and well-located in Ashland. Amenities were great, and having three en-suite bedrooms was perfect. Host communicated well and often to ensure trouble-free experience. Fully equipped kitchen ideal for anyone to enjoy.We highly recommend this property!"
United States
Paul B.
The price is £439
includes taxes & fees
19 Oct - 20 Oct
The Ashland Social | Main House
A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

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)
"This is our favorite spot to stay in Ashland! The location is perfect for walking downtown to the shops and theaters, shopping at the local co-op, or just enjoying a sunny breakfast on the deck."
United States
Julia W.
The price is £299
includes taxes & fees
5 Oct - 6 Oct
Charming house two blocks from downtown Ashland
A garden with a white fence, green hedges, and purple flowering trees.

18. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
The price is £242
includes taxes & fees
5 Oct - 6 Oct
Whimsy on B | 2BR Steps to Downtown
A two-story house with a porch, a small garden, and a metal fence.

19. Savage Upon Siskiyou | Prime OSF Location

Savage Upon Siskiyou | Prime OSF Location
Siskiyou-Hargadine Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Great location. Easy to walk everywhere. Thanks for great stay"
United States
Anonymous traveller
The price is £354
includes taxes & fees
6 Oct - 7 Oct
Savage Upon Siskiyou | Prime OSF Location
A two-story house with a blue front door, number 485, surrounded by well-maintained lawns and flowering trees.

20. The Ashland Social | Entire Estate

The Ashland Social | Entire Estate
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Lovely house. Works well for a large group. Do bee aware that yard and pool maintenance crews may be there during your stay."
United States
Donna M.
The price is £544
includes taxes & fees
19 Oct - 20 Oct
The Ashland Social | Entire Estate
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
"The location was perfect. We were just a short walk away from Ashland's quaint downtown, eateries, and the Cabaret Theater. Breakfast was good and we loved that we had two sinks apart from our bathroom. That made getting ready a snap."
Gale 2-night trip
Posted 1 hour ago
Stratford Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
550
Accommodation
277 Holiday Homes
Lowest Price
£149
Highest Price
£544