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Search results; 986 homes in Ashland

Top guest favourite
Guest house in Ashland
Charming cottage, walk to town.
1 bedroom, 2 beds, 1.5 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 553 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 111 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
Guest favourite
Room in Phoenix
Cozy Room with Mountain View
4.95 out of 5 average rating, 78 reviews, 1 sofa bed, No bathroom
5–10 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
Apartment in Ashland
Plaza North Suite 203 Windsor
4.98 out of 5 average rating, 57 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
28 Aug – 2 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
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
Guest favourite
Bungalow in Ashland
Hanna's House | Downtown Retreat, Steps to OSF
5.0 out of 5 average rating, 40 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Ashland
Manzanita Cottage
4.98 out of 5 average rating, 211 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
Superhost
Tiny home in Ashland
Walk to town! Cozy Forest Teeny House
4.81 out of 5 average rating, 186 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 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
Home in Ashland
Abram's Cottage
4.93 out of 5 average rating, 122 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
Superhost
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
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
4.95 out of 5 average rating, 584 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.88 out of 5 average rating, 207 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Ashland
Clean, Stylish Apt w/kitchen. block from Downtown
4.89 out of 5 average rating, 864 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 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
Top guest favourite
Guest house in Ashland
Modern Airy Retreat - Views, Walk to Everything
4.96 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Farm stay in Ashland
Kelly’s Carriage House 4 miles from Ashland
4.97 out of 5 average rating, 375 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Sept