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Search results; Over 1,000 homes in Ashland

Guest favourite
Cottage in Ashland
Oak Tower Cottage
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Jan
,
4.86 out of 5 average rating, 56 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 110 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
Guest favourite
Cabin in Ashland
Bluemoon Vacation Rentals - Cabin 52
4.84 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Guest house in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
4.98 out of 5 average rating, 270 reviews, 2 beds, 1 bathroom
22–27 Jul
Home in Ashland
Come Stroll-Inn downtown Ashland
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
27 Jul – 1 Aug
Superhost
Dome in Ashland
The Acorn dome w/ sauna
4.8 out of 5 average rating, 215 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Top guest favourite
Room in Ashland
Château Herbe ~ Vienna Room
4.91 out of 5 average rating, 114 reviews, 1 king bed, 1 bathroom
24–29 Jul
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
4.77 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Ashland
Abram's Cottage
4.93 out of 5 average rating, 122 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
4.96 out of 5 average rating, 149 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Room in Ashland
Wood Hamlet - Noble Forest Room Private by DownTn
4.97 out of 5 average rating, 221 reviews, 1 queen bed, 1 bathroom
14–19 Aug
Top guest favourite
Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
4.93 out of 5 average rating, 808 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Superhost
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
4.84 out of 5 average rating, 74 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Cabin in Ashland
Whispering Pines Cabin near Hyatt Lake
4.91 out of 5 average rating, 43 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Apartment in Ashland
Plaza North Suite 201 Alexander
5.0 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
Superhost
Home in Ashland
Savage Upon Siskiyou | Prime OSF Location
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Dome in Jacksonville
The Sky Dome at Yale Creek Ranch
4.98 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Guest suite in Ashland
RedTail Inn - Red McCall Suite | Sleeps up to 6
4.97 out of 5 average rating, 115 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.88 out of 5 average rating, 206 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug