The Best Airbnb Deals in
Ashland, Oregon

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Ashland, Oregon. Enter your travel dates to find the best deals!

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AirDNA Score: 93
$345/night

Ashland Meadows: Ideal for Friends & Family

3 beds
2.5 baths
5 guests
Average Price:  
$381
9% Cheaper
than normal
AirDNA Score: 86
$149/night

Downtown Cottage - Great Views - 1 Block to OSF!

1 bed
1 bath
2 guests
Average Price:  
$166
10% Cheaper
than normal
AirDNA Score: 86
$155/night

executive retreat overlooking Ashland w/ views

1 bed
1 bath
2 guests
Average Price:  
$355
56% Cheaper
than normal
AirDNA Score: 86
$124/night

Jazzy B Suite~Historic, eco/dog friendly

1 bed
1 bath
3 guests
Average Price:  
$134
7% Cheaper
than normal
AirDNA Score: 83
$175/night

Secluded Forest Log House 15 minutes to Ashland

2 beds
1.5 baths
5 guests
Average Price:  
$206
15% Cheaper
than normal
AirDNA Score: 79
$128/night

The West Wing-Stay Rogue

1 bed
1 bath
2 guests
Average Price:  
$133
4% Cheaper
than normal
AirDNA Score: 79
$190/night

Historic Stage Coach Stop

1 bed
1 bath
2 guests
Average Price:  
$197
4% Cheaper
than normal
AirDNA Score: 77
$200/night

Coyote Moon

2 beds
2 baths
4 guests
Average Price:  
$216
7% Cheaper
than normal
AirDNA Score: 77
$129/night

Owl House in the Oaks

studio
1 bath
2 guests
Average Price:  
$147
12% Cheaper
than normal
AirDNA Score: 76
$205/night

Beautiful and peaceful cottage close to downtown

1 bed
2 baths
5 guests
Average Price:  
$228
10% Cheaper
than normal
AirDNA Score: 75
$124/night

The Pioneer House -North Suite (Upstairs) - Closest to OSF!

2 beds
1 bath
6 guests
Average Price:  
$243
49% Cheaper
than normal
AirDNA Score: 73
$350/night

Meadow House at Willow-Witt Ranch

3 beds
2 baths
10 guests
Average Price:  
$402
13% Cheaper
than normal
AirDNA Score: 73
$300/night

Sunset Chalet

3 beds
2 baths
12 guests
Average Price:  
$348
14% Cheaper
than normal
AirDNA Score: 72
$139/night

JJ''s Loft | Downtown | Large Deck | Kitchenette

1 bed
1 bath
2 guests
Average Price:  
$140
1% Cheaper
than normal
AirDNA Score: 71
$129/night

Private Garden Cottage w Sauna in RR District

1 bed
1 bath
4 guests
Average Price:  
$152
15% Cheaper
than normal
AirDNA Score: 71
$183/night

High Street Cottage- Artist''s Garden Cottage

2 beds
1 bath
4 guests
Average Price:  
$201
9% Cheaper
than normal
AirDNA Score: 71
$105/night

Comfortable, Private Guest Lodging

1 bed
1 bath
3 guests
Average Price:  
$114
8% Cheaper
than normal
AirDNA Score: 71
$230/night

ABBOTT''S COTTAGES - Falcon

2 beds
2 baths
6 guests
Average Price:  
$231
0% Cheaper
than normal
AirDNA Score: 70
$295/night

Central Avenue Cottages

2 beds
2 baths
4 guests
Average Price:  
$275
7% More
than normal
AirDNA Score: 69
$144/night

RedTail ~ McCall Suite~Tesla Station~ 4 Blocks to OSF!

2 beds
1 bath
6 guests
Average Price:  
$169
15% Cheaper
than normal
AirDNA Score: 68
$195/night

Charming Space Next to Everything, Walk Anywhere!

1 bed
1 bath
4 guests
Average Price:  
$228
14% Cheaper
than normal
AirDNA Score: 67
$249/night

Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen

5 beds
5 baths
11 guests
Average Price:  
$505
51% Cheaper
than normal
AirDNA Score: 67
$99/night

#48 The Cabins on Hyatt Prairie - Sleeps 4 - Hot Tub

2 beds
1 bath
4 guests
Average Price:  
$227
56% Cheaper
than normal
AirDNA Score: 65
$270/night

AGC Carriage House 4 Blocks to Plaza Private

2 beds
2 baths
4 guests
Average Price:  
$296
9% Cheaper
than normal
AirDNA Score: 65
$174/night

#32 & #33 Hyatt Prairie Compound - Hot Tub- Sleeps 12- Kitchen

4 beds
2 baths
12 guests
Average Price:  
$441
61% Cheaper
than normal
AirDNA Score: 64
$125/night

Lori Lanes ''Juliet Cottage'' ~ 2 Bedroom ~ 5 Blocks to Downtown Ashland ~Kitchen

2 beds
1 bath
4 guests
Average Price:  
$193
35% Cheaper
than normal
AirDNA Score: 64
$249/night

Ashland Haus Retreat - 1 block from downtown!

2 beds
1 bath
6 guests
Average Price:  
$271
8% Cheaper
than normal
AirDNA Score: 63
$154/night

AGC-Oberon 4 Blocks to Plaza, OSF, Lithia Park

1 bed
1 bath
2 guests
Average Price:  
$160
4% Cheaper
than normal
AirDNA Score: 63
$179/night

AGC Garden Cottage 4 Blocks 2 Plaza

studio
1 bath
2 guests
Average Price:  
$193
7% Cheaper
than normal
AirDNA Score: 62
$99/night

#47 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

2 beds
1 bath
6 guests
Average Price:  
$227
56% Cheaper
than normal
AirDNA Score: 61
$170/night

Historic Cottage close to plaza

1 bed
1 bath
3 guests
Average Price:  
$175
3% Cheaper
than normal
AirDNA Score: 60
$99/night

#33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

2 beds
1 bath
6 guests
Average Price:  
$229
57% Cheaper
than normal
AirDNA Score: 59
$300/night

Relax & work in a country space.

4 beds
2 baths
9 guests
Average Price:  
$369
19% Cheaper
than normal
AirDNA Score: 59
$120/night

Bear Hollow Retreat

2 beds
2 baths
4 guests
Average Price:  
$135
11% Cheaper
than normal
AirDNA Score: 59
$295/night

Titania - Second Spring Property

1 bed
1 bath
3 guests
Average Price:  
$312
5% Cheaper
than normal
AirDNA Score: 58
$323/night

Ashland Lodge w/ Lake Views & Patio: Fish On-Site!

4 beds
3 baths
13 guests
Average Price:  
$485
33% Cheaper
than normal
AirDNA Score: 57
$250/night

4th St Inn Garden flat - sleeps 6

3 beds
2 baths
6 guests
Average Price:  
$292
14% Cheaper
than normal
AirDNA Score: 57
$175/night

Porscha''s 2 Bedroom Deluxe Stunning!

2 beds
1 bath
2 guests
Average Price:  
$206
15% Cheaper
than normal
AirDNA Score: 56
$250/night

Brenden House, Main

3 beds
2.5 baths
8 guests
Average Price:  
$261
4% Cheaper
than normal
AirDNA Score: 55
$99/night

#44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

2 beds
1 bath
6 guests
Average Price:  
$227
56% Cheaper
than normal
AirDNA Score: 54
$299/night

Garden Suite (sleeps five-two full baths) downtown

2 beds
2 baths
5 guests
Average Price:  
$351
15% Cheaper
than normal
AirDNA Score: 51
$300/night

Abigail''s Self Catering Vacation Cottage Two Rooms

2 beds
1.5 baths
4 guests
Average Price:  
$207
45% More
than normal
AirDNA Score: 50
$128/night

The Loft Nancy''s Cottage

1 bed
1 bath
2 guests
Average Price:  
$134
4% Cheaper
than normal
AirDNA Score: 50
$275/night

Nancy''s Garden Cottage - Main House

1 bed
1 bath
2 guests
Average Price:  
$250
10% More
than normal
AirDNA Score: 50
$100/night

The Loft at Breden House

1 bed
1 bath
2 guests
Average Price:  
$131
24% Cheaper
than normal
AirDNA Score: 49
$385/night

Sherwin Cottage

2 beds
2 baths
11 guests
Average Price:  
$419
8% Cheaper
than normal
AirDNA Score: 49
$358/night

Oak Tower Cottage

2 beds
2 baths
8 guests
Average Price:  
$379
6% Cheaper
than normal
AirDNA Score: 43
$275/night

Clean, Well Appointed & Close to Downtown Ashland!

3 beds
2.5 baths
6 guests
Average Price:  
$326
16% Cheaper
than normal
AirDNA Score: 42
$99/night

#45 The Cabins on Hyatt Prairie - Sleeps 4 - Hot Tub

2 beds
1 bath
4 guests
Average Price:  
$192
48% Cheaper
than normal
AirDNA Score: 39
$250/night

3 bedroom house, walking distance from downtown

3 beds
1.5 baths
6 guests
Average Price:  
$280
11% Cheaper
than normal
AirDNA Score: 33
$99/night

#32 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub

2 beds
1 bath
6 guests
Average Price:  
$229
57% Cheaper
than normal
AirDNA Score: 33
$349/night

Anne Hathaway''s House ~ Just 4 blocks from OSF!~ Kitchen & Laundry

7 beds
8.5 baths
13 guests
Average Price:  
$560
38% Cheaper
than normal
AirDNA Score: 32
$99/night

#49 The Cabins on Hyatt Prairie - Sleeps 4 - Hot Tub- Full Kitchen

2 beds
1 bath
4 guests
Average Price:  
$212
53% Cheaper
than normal
AirDNA Score: 31
$174/night

#47 & 48 Hyatt Prairie Compound - Sleeps 9

4 beds
2 baths
9 guests
Average Price:  
$414
58% Cheaper
than normal
AirDNA Score: 29
$275/night

B Street Beauty, Around The Corner From Plaza

3 beds
2.5 baths
10 guests
Average Price:  
$325
15% Cheaper
than normal
AirDNA Score: 29
$165/night

Cozy, Clean and Comfortable!

2 beds
1 bath
4 guests
Average Price:  
$215
23% Cheaper
than normal
AirDNA Score: 29
$299/night

RedTail Suites ~ Entire Home ~ Sleeps 12 ~ Tesla Station~ 4 Blocks to OSF!

4 beds
3 baths
12 guests
Average Price:  
$370
19% Cheaper
than normal
AirDNA Score: 27
$195/night

ArtyCottage built by a custom furniture maker.

2 beds
1.5 baths
3 guests
Average Price:  
$202
3% Cheaper
than normal
AirDNA Score: 21
$175/night

Spur Rail Loft House~ A few blocks to Downtown Ashland~ Mountain Views ~ Kitchen

3 beds
2 baths
6 guests
Average Price:  
$327
46% Cheaper
than normal