Home Vacation Rentals By Owner In Ashland, OR

Showing 60 Of 214 Vacation Rentals
Slider Thumb
Exceptional(6)

$1034.02

/ Nightly
Apartment

Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.

Ashland, Oregon, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(13)

$324.07

/ Nightly
Apartment

Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!

Ashland, Oregon, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(10)

$262.25

/ Nightly
Apartment

Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(5)

$324.09

/ Nightly
Cottage

ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown

Ashland, Oregon, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(6)

$186.81

/ Nightly
Apartment

ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(2)

$341.75

/ Nightly
Cottage

Abbott's Cottages- The Raven. Two bedroom cottage just two blocks to downtown.

Ashland, Oregon, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(10)

$285.9

/ Nightly
Private Vacation Home

ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown

Ashland, Oregon, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(4)

$206.23

/ Nightly
Cottage

ABBOTT'S COTTAGES- Duck cottage. 1 bedroom/1 bath, walking distance to downtown!

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(3)

$222.69

/ Nightly
Cottage

Abbott's Cottages- The Heron. One bedroom cottage just two blocks to downtown

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(5)

$370.39

/ Nightly
Private Vacation Home

ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown

Ashland, Oregon, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(5)

$206.23

/ Nightly
Cottage

ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(76)

$251.28

/ Nightly
Cottage

Courtside Cottage - WalkScore 93 - Dog Friendly

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(107)

$178.64

/ Nightly
Apartment

Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(61)

$220.4

/ Nightly
Cottage

20% off OSF tix in B&C sections for guests! 5-min walk to downtwn, private yard

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
Slider Thumb
Exceptional(40)

$166.46

/ Nightly
Castle

Chateau Herbe ~ Athens Room

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(22)

$166.46

/ Nightly
Castle

Chateau Herbe ~ Vienna Room

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(37)

$166.46

/ Nightly
Castle

Florence Room at Chateau Herbe

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(13)

$71.23

/ Nightly
Apartment

Top floor of modern duplex - walk to plays, SOU, Lithia Park

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(28)

$223.02

/ Nightly
Apartment

The Ashland Social | Guest Studio

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$509.56

/ Nightly
Private Vacation Home

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Ashland, Oregon, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
map-loader

Home Rent a place that suits your needs

Private vacation home

Private vacation home

View 92 Private vacation home

Home Most popular vacation rentals in Ashland

Slider Thumb
Exceptional(99)

$230.14

/ Nightly
Cottage

Charming carriage house in Ashland near downtown

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(99)

$249.79

/ Nightly
Private vacation home

Chateau Herb ~ Miranda Carriage House Apt

Ashland, Oregon, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(99)

$248.50

/ Nightly
Private vacation home

Cabin #4 at Hyatt Lake Resort

Jackson County, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$246.64

/ Nightly
Bed & breakfast

Ashland's Premier Eco-B&B: Dog-friendly Queen Bed Room with Separate Entrance (Pertelote)

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$245.33

/ Nightly
Private vacation home

Whimsy on B | The Studio

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$241.58

/ Nightly
Cottage

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$233.39

/ Nightly
Hotel

Ashland 2 Double Suite w/Gym & pool

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(99)

$213.66

/ Nightly
Private vacation home

Peaceful 1-bedroom bungalow with AC in charming Ashland

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$212.97

/ Nightly
Apartment

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Ashland, Oregon, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(99)

$213.25

/ Nightly
Private vacation home

Peaceful, spacious home on 8 acres. Pet-friendly, close to town, and a creek!

Ashland, Oregon, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Most Popular Cities in Oregon