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Search results; 959 homes in Ashland

Top guest favourite
Guest suite in Ashland
Eco-friendly Woodland Retreat
2 bedrooms, 3 beds, 1 private bathroom
22–27 Aug
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4.98 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Ashland
Sweet Breeze Bungalow
4.98 out of 5 average rating, 133 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Sept
Home in Medford
Cozy Cottage
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Jul
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 112 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Nov
Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
4.97 out of 5 average rating, 413 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
4.96 out of 5 average rating, 155 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
Dome in Ashland
The Acorn dome w/ sauna
4.8 out of 5 average rating, 220 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Superhost
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
4.83 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Ashland
Wood Hamlet - Miro Room, walk to town
4.97 out of 5 average rating, 232 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
4.91 out of 5 average rating, 47 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Room in Ashland
Cozy/rural close to town
4.9 out of 5 average rating, 944 reviews, 1 queen bed, 1 bathroom
25–30 Jul
Superhost
Cabin in Ashland
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
4.77 out of 5 average rating, 47 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Ashland
Château Herbe ~ Vienna Room
4.9 out of 5 average rating, 115 reviews, 1 king bed, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Home in Talent
Beautiful 3-bedroom Family House
4.86 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
Guest favourite
Flat in Ashland
Beautiful Ashland Flat
4.82 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Home in Medford
Modern Pet-Friendly Stay | Near Downtown Medford
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Aug
Home in Ashland
Oregon Mountain Lodge
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Jul
Superhost
Cabin in Ashland
Bluemoon Vacation Rentals - Cabin 52
4.84 out of 5 average rating, 115 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.89 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug