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Search results; 965 homes in Ashland

Top guest favourite
Flat in Ashland
The Carriage House, Winner 2025 Best of Ashland!
1 bedroom, 2 beds, 1 private bathroom
21–26 Aug
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4.89 out of 5 average rating, 293 reviews
Guest favourite
Place to stay in Ashland
Walk to town! Ashland Paris Room
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.85 out of 5 average rating, 95 reviews
Home in Medford
Viewtacular Estate House, Pool, Hot tub & Sauna!
4 bedrooms, 4 beds, 3.5 bathrooms
4–9 Aug
New place to stay
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.97 out of 5 average rating, 114 reviews
Guest favourite
Guest house in Ashland
1853 Farmhouse-country yet five minutes to Ashland
2 bedrooms, 1 bed, 1 bathroom
2–7 Aug
4.8 out of 5 average rating, 40 reviews
Top guest favourite
Hotel room in Ashland
Swank Suites | King with Lux Tub
1 king bed, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 92 reviews
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Aug
4.78 out of 5 average rating, 157 reviews
Guest favourite
Cottage in Talent
Paschal Winery - Dream 1 Cottage
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.93 out of 5 average rating, 71 reviews
Hotel in Ashland
Ashland Abode | Swim. Ski Nearby.
1 bedroom, 2 queen beds, 1 bathroom
1–6 Aug
4.72 out of 5 average rating, 36 reviews
Top guest favourite
Guest suite in Ashland
Wood Hamlet - Miro Room, walk to town
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 233 reviews
Top guest favourite
Guest house in Ashland
Modern Airy Retreat - Views, Walk to Everything
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 208 reviews
Top guest favourite
Guest house in Ashland
Ashland Artist Country Retreat
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 146 reviews
Home in Ashland
Oregon Mountain Lodge
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Guest house in Ashland
Charming cottage, walk to town.
1 bedroom, 2 beds, 1.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 557 reviews
Top guest favourite
Home in Ashland
Pioneer Vacation Rentals - Pioneer Craftsman House
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
4.96 out of 5 average rating, 53 reviews
Dome in Ashland
The Acorn dome w/ sauna
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.8 out of 5 average rating, 222 reviews
Top guest favourite
Guest house in Ashland
Mindy’s Ashland Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.9 out of 5 average rating, 182 reviews
Guest favourite
Home in Ashland
Beautiful and peaceful cottage close to downtown
1 bedroom, 2 beds, 2 bathrooms
15–20 Aug
4.91 out of 5 average rating, 161 reviews