We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Ashland Cottages

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
0 rentals in Ashland.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
The Ashland Cottage, walk to town
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

In the historic railroad district, walking distance to all the best of Ashland!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Craftsman Style Home In Country Setting
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Hanna's House- Your Home Away from Home
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Front of rental
downstairs washer/dryer
Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Brand New Custom Ashland Home with Fantastic Mountain Views
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Railroad District, steps to downtown, everything you need to enjoy Ashland!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Asian Inspired Escape with View - Just 3 Miles from Downtown
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

High Street Cottage Artists' Garden Cottage Clean & Beautiful
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248)
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Save time - get the best Ashland rentals sent straight to your email!
Walk to town from this Charming Cottage.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

The Aloha House~ Hot Tub~ Seasonal Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Hyatt Lake Mountain Retreat
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

The Maple Apartment at Tudor House Vacation Rentals
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Hyatt Praire Mountain Cabin
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

ArtYcottage UNBELIEVEABLE...
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Hyatt Prairie Cabin #33 ~ Hot Tub
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Quiet and peaceful cottage close to downtown
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Hyatt Prairie Cabin #46~ Hot Tub~ Dog Friendly
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

The Perfect Vacation Cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

The Madrone House, Country Getaway with Panoramic Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

ArtYCottage - custom furniture and art through out. Secluded and fabulous!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Mt. Ashland Homestead's Secluded Forest House, 15 minutes from Ashland
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

The Terra Cottage Inn a beautiful Luxury Apartment
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Hyatt Prairie Cabin #44 ~ Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Hyatt Prairie Mountain Cabin
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Stunning studio, Italian Motif, Walk to Town.
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Come relax, work & enjoy country air. Winter is beautiful. WiFi.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Charming Space Next to Everything, Walk Anywhere!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Private Suite Near Shakespeare
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Pioneer North Suite (Upstairs)~ Close to OSF
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Pioneer Craftsman- Closest to OSF!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

OCTOBER in COZY cottage near Lithia Park and Town! Ashland, OR
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Hyatt Prairie Cabin #45 ~ Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out

Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

The High Street Cottage An Artists' Garden Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Charming, Comfortable Garden Studio Above The University.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Helman House-Three Blocks from the Oregon Shakespeare Festival
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Whispering Pines~ Dog Friendly ~Kitchen
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

The Dogwood Suite at Tudor House Vacation Rentals
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out