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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Ashland vacation homes

Interior

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
10 Aug - 11 Aug
Savage Upon Siskiyou
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 949
AED 1,705 total
includes taxes & fees
26 Jul - 27 Jul
Grandview of Ashland
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 878
AED 1,511 total
includes taxes & fees
26 Jul - 27 Jul
The Mountain Ave House by WanderLodges
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 625
AED 979 total
includes taxes & fees
10 Aug - 11 Aug
Hanna's House by WanderLodges
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

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 727
AED 1,281 total
includes taxes & fees
9 Aug - 10 Aug
Barclay Klum House by WanderLodges
Exterior

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Perfect huge Chateau territory! Clean rooms) quiet territory. The hosts are always available. "
United States
Irina
The price is AED 812
AED 1,104 total
includes taxes & fees
20 Aug - 21 Aug
Chateau Herb ~ Miranda Carriage House Apt
Living area

1907 Charmer, Perfect Downtown Location, So Clean!

1907 Charmer, Perfect Downtown Location, So Clean!
Historic Downtown District
9.4 out of 10, Exceptional, (133 reviews)
"Great stay!"
United States
Bettina T.
The price is AED 1,163
AED 2,271 total
includes taxes & fees
26 Jul - 27 Jul
1907 Charmer, Perfect Downtown Location, So Clean!
Smart TV

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (51 reviews)
"Len provided me with an outdoor table and extra chairs so I could have dinner outside with my family because one had the flu. So wonderful to be able to socialize with everyone without risking getting the flu! House was very comfortable and well supplied. Close to downtown and hiking. Off street parking for one car. Thank you so much!!!"
United States
Judy
East Main Downtown Bungalow
Coffee/tea maker, fridge, microwave, oven

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, (71 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is AED 878
AED 2,044 total
includes taxes & fees
20 Aug - 21 Aug
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
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.
The price is AED 602
AED 1,100 total
includes taxes & fees
10 Aug - 11 Aug
Hanna`s House | Downtown Retreat, Steps to OSF
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.
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
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!
Coffee/tea maker, fridge, microwave, oven

Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (68 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 AED 680
AED 1,212 total
includes taxes & fees
27 Jul - 28 Jul
Quiet and peaceful cottage close to downtown
Property grounds

Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.6 out of 10, Exceptional, (11 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 - Pet Friendly

Swank Suites | Step Free King - Pet Friendly
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 - Pet Friendly
Exterior

The Ashland Social | Entire Estate

The Ashland Social | Entire Estate
Ashland
10.0 out of 10, Exceptional, (15 reviews)
"Very clean house with a beautiful kitchen. Spacious for our family and quiet. Would go back "
United States
Diana S.
The price is AED 2,116
AED 4,137 total
includes taxes & fees
25 Jul - 26 Jul
The Ashland Social | Entire Estate
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, (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 AED 992
AED 1,257 total
includes taxes & fees
20 Aug - 21 Aug
Moody Ashland Escape: Luxe Suite, Copper Tub
Exterior

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!
Interior

The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (34 reviews)
"Gorgeous place! Especially enjoyed the pool and hot tub! Very comfy, quiet, and we loved the location. "
United States
Pretty W.
The price is AED 1,866
AED 3,586 total
includes taxes & fees
25 Jul - 26 Jul
The Ashland Social | Main House
Exterior

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 AED 643
AED 1,520 total
includes taxes & fees
10 Aug - 11 Aug
Savage Upon Siskiyou | Prime OSF Location
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
"We've stayed other places but this hotel is better, because of the location, indoor hallways, and the indoor swimming pool. It's a 10-15 min walk to the Shakespeare theaters and downtown. We weren't hungry with the complimentary breakfast (oatmeal, yogurt, toast, bagels, boiled eggs, etc), and it's across the street from Safeway supermarket. Some rooms have refrigerator and microwave, and some have kitchenette. We prefer the "mountain side" rooms that are away from the street. The price is great and so we can ignore that some items need a refresh - our bathroom sink was stained etc. Everything worked and we were comfortable - we've stayed here before and will be happy to stay again."
Ruth 6-night trip
Posted 1 hour ago
Stratford Inn

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