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Search results; 962 homes in Ashland

Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
1 bedroom, 2 beds, 1 bathroom
10–15 Nov
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.95 out of 5 average rating, 597 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
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, 228 reviews
Guest favourite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
2 bedrooms, 3 beds, 3 bathrooms
10–15 Aug
4.97 out of 5 average rating, 37 reviews
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Cottage in Ashland
Vineyard Cottage-Winery, Hot Tub, Privacy
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.93 out of 5 average rating, 262 reviews
Top guest favourite
Guest house in Ashland
Charming cottage, walk to town.
1 bedroom, 2 beds, 1.5 bathrooms
18–23 Oct
4.98 out of 5 average rating, 560 reviews
Guest favourite
Home in Phoenix
Artsy MCM Guesthouse w/ Spa Soaking Tub
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.83 out of 5 average rating, 161 reviews
Tiny home in Ashland
Geodome and tiny home combo
2 bedrooms, 1 queen bed, 2 bathrooms
17–22 Aug
Guest favourite
Home in Medford
Modern Creekside Retreat • Walk to Asante
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Bungalow in Ashland
Hanna's House | Downtown Retreat, Steps to OSF
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 41 reviews
Guest favourite
Flat in Ashland
Château Herbe ~ Oberon Private suite w/ Kitchen
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.77 out of 5 average rating, 26 reviews
Top guest favourite
Farm stay in Ashland
Kelly’s Carriage House 4 miles from Ashland
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 380 reviews
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.89 out of 5 average rating, 212 reviews
Top guest favourite
Room in Talent
Talent Home/Room with a View
1 queen bed, 1 bathroom
2–7 Sept
4.97 out of 5 average rating, 179 reviews
Guest favourite
Camper van/Motorhome in Ashland
Walk to town! The Deep Blue Metallic Dream Machine
1 bedroom, 1 king bed, 1 bathroom
8–13 Aug
4.86 out of 5 average rating, 206 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, 159 reviews