Search results; 960 homes in Ashland

Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 413 reviews
Top guest favourite
Cottage in Ashland
Sweet Breeze Bungalow
2 beds
12–17 Sept
4.98 out of 5 average rating, 133 reviews
Home in Medford
Cozy Cottage
2 queen beds
17–22 Jul
New place to stay
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
2 beds
10–15 Nov
4.97 out of 5 average rating, 112 reviews
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
2 king beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 155 reviews
Dome in Ashland
The Acorn dome w/ sauna
1 queen bed
16–21 Aug
4.8 out of 5 average rating, 220 reviews
Superhost
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
1 bed
26–31 Jul
4.83 out of 5 average rating, 76 reviews
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
3 beds
17–22 Jul
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Guest suite in Ashland
Wood Hamlet - Miro Room, walk to town
1 queen bed
28 Sept – 3 Oct
4.97 out of 5 average rating, 232 reviews
Guest favourite
Home in Talent
Beautiful 3-bedroom Family House
3 beds
28 Aug – 2 Sept
4.86 out of 5 average rating, 42 reviews
Superhost
Cabin in Ashland
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
1 queen bed
2–7 Aug
4.77 out of 5 average rating, 47 reviews
Guest favourite
Room in Ashland
Stay with Esther
Château Herbe ~ Vienna Room
31 Jul – 5 Aug
4.9 out of 5 average rating, 115 reviews
Top guest favourite
Room in Ashland
Stay with Joe
Cozy/rural close to town
25–30 Jul
4.9 out of 5 average rating, 944 reviews
Home in Medford
Modern Pet-Friendly Stay | Near Downtown Medford
2 queen beds
7–12 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Ashland
Beautiful Ashland Flat
1 queen bed
26–31 Jul
4.82 out of 5 average rating, 17 reviews
Superhost
Cabin in Ashland
Bluemoon Vacation Rentals - Cabin 52
3 beds
3–8 Aug
4.84 out of 5 average rating, 115 reviews
Guest favourite
Guest suite in Ashland
RedTail Inn - Louisa Suite | Hot Tub |DWTN
1 queen bed
2–7 Aug
4.91 out of 5 average rating, 74 reviews
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
1 queen bed
9–14 Aug
4.89 out of 5 average rating, 209 reviews