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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is NZ$459
includes taxes & fees
7 Sept - 8 Sept
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, (52 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.
East Main Downtown Bungalow
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

3. 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 NZ$574
includes taxes & fees
31 Aug - 1 Sept
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

4. 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 NZ$663
includes taxes & fees
14 Sept - 15 Sept
Grandview of Ashland
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

5. 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 NZ$448
includes taxes & fees
10 Sept - 11 Sept
Hanna's House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

6. 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 NZ$708
includes taxes & fees
31 Aug - 1 Sept
Savage Upon Siskiyou
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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.
Hanna`s House | Downtown Retreat, Steps to OSF
A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

8. 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.
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

9. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (10 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 NZ$424
includes taxes & fees
31 Aug - 1 Sept
Chateau Herb ~ Miranda Carriage House Apt
An outdoor patio area with multiple tables and chairs, surrounded by striped umbrellas.

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
A two-story house with a porch, a wooden fence, and a paved driveway.

11. 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.
Downtown Ashland House - Walk to Plaza and OSF!
A kitchen with granite countertops, dark cabinetry, and a refrigerator.

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 price is NZ$551
includes taxes & fees
28 Sept - 29 Sept
Quiet and peaceful cottage close to downtown
A garden with a white fence, green hedges, and purple flowering trees.

13. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
Whimsy on B | The Studio
A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

14. 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, (76 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is NZ$827
includes taxes & fees
7 Sept - 8 Sept
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
A hallway with a blue wall, a framed welcome sign, a round mirror, and a table.

15. The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (35 reviews)
The Ashland Social | Main House
A garden with a white fence, green hedges, and purple flowering trees.

16. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
Whimsy on B | 2BR Steps to Downtown
A bedroom with a large bed, a chandelier, a desk, a chair, and a window with curtains.

17. 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.
Moody Ashland Escape: Luxe Suite, Copper Tub
A residential property with a pathway leading to a house, surrounded by a wooden fence, and featuring a small patio area.

18. Come Stroll-inn in Downtown Ashland

Come Stroll-inn in Downtown Ashland
Siskiyou-Hargadine Historic District
Come Stroll-inn in Downtown Ashland
A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

19. 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.
Charming house two blocks from downtown Ashland
A deck with a fire pit, seating, and a view of the mountains.

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.
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.
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Top Ashland Hotel Reviews

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

10/10 Excellent
"Our stay at Plaza Inn was wonderful! It is a great property and perfectly located to walk to the Shakespeare theatre, all the amazing shops and great restaurants. The staff are super helpful also. I would stay here again!!!"
Kathleen 1-night trip
Posted 1 hour ago
Plaza Inn & Suites at Ashland Creek

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
519
Accommodation
277 Holiday Homes
Lowest Price
NZ$424
Highest Price
NZ$827