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Search results; 953 homes in Ashland

Top guest favourite
Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
1 bedroom, 2 beds, 1 private bathroom
19–24 Aug
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4.93 out of 5 average rating, 817 reviews
Top guest favourite
Flat in Ashland
The Carriage House, Winner 2025 Best of Ashland!
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.89 out of 5 average rating, 295 reviews
Guest favourite
Cottage in Talent
Paschal Winery - Dream 1 Cottage
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.93 out of 5 average rating, 72 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, 232 reviews
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Farm stay in Ashland
Kelly’s Carriage House 4 miles from Ashland
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 388 reviews
Top guest favourite
Guest house in Ashland
C Street Station Cottage
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 187 reviews
Guest favourite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
2 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Ashland
RedTail Inn - Red McCall Suite | Sleeps up to 6
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 121 reviews
Guest favourite
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
1 bedroom, 1 bed, 1 bathroom
26–31 Aug
4.84 out of 5 average rating, 87 reviews
Home in Ashland
Ashland creekside home w/ sauna
3 bedrooms, 3 queen beds, 1 bathroom
27 Aug – 1 Sept
4.68 out of 5 average rating, 75 reviews
Top guest favourite
Room in Medford
Private Pulchritudinous 1918 Suite
1 queen bed, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 659 reviews
Guest favourite
Cottage in Ashland
Charming very well appointed cottage !
1 bedroom, 1 king bed, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 492 reviews
Home in Medford
Country Road 2 bedroom
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
New place to stay
Guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 604 reviews
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
2 bedrooms, 2 king beds, 2 bathrooms
10–15 Oct
4.96 out of 5 average rating, 161 reviews
Superhost
Tiny home in Ashland
Walk to town! Cozy Forest Teeny House
1 bedroom, 1 bed, 1 bathroom
20–25 Aug
4.79 out of 5 average rating, 195 reviews
Guest favourite
Home in Talent
Dream House at Paschal Winery
3 bedrooms, 3 beds, 3.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Ashland
Creekside Retreat Close to Town
2 bedrooms, 3 beds, 1.5 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 253 reviews