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
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Log in
to get trip updates and message other travellers.
Ashland
Ashland Tourism
Ashland Hotels
Bed and Breakfast Ashland
Ashland Holiday Rentals
Ashland Holiday Packages
Flights to Ashland
Ashland Attractions
Ashland Travel Forum
Ashland Photos
Ashland Map
Ashland Guide
Hotels
All Ashland Hotels
Ashland Hotel Deals
Last Minute Hotels in Ashland
By Hotel Type
By Hotel Class
By Hotel Brand
Popular Amenities
Popular Ashland Categories
Near Airports
Ashland Motels
Ashland Hostels
Ashland Campgrounds
Business Hotels Ashland
Ashland Green Hotels
Family Hotels Ashland
Romantic Hotels in Ashland
Spa Hotels in Ashland
5-stars Hotels in Ashland
4-stars Hotels in Ashland
3-stars Hotels in Ashland
Choice Hotels in Ashland
Pet Friendly Hotels in Ashland
Ashland Hotels with a Pool
Hotels with Smoking Rooms in Ashland
Boutique Hotels Ashland
Couples Hotels in Ashland
Ashland Spa Hotels
Unique Hotels Ashland
Ashland Hotels With Indoor Pools
City Centre Hotels in Ashland
Themed Hotels Ashland
Wedding Hotels Ashland
Convention Hotels in Ashland
Hotels near (MFR) Jackson County Airport
Things to do
Restaurants
Flights
Holiday Rentals
By Holiday Rental Type
Popular Amenities
Places of Interest
House Rentals in Ashland
Apartment Rentals in Ashland
Cabin Rentals in Ashland
Cottages in Ashland
Cheap Ashland Holiday Rentals
Ashland Luxury Holiday Rentals
Pet Friendly Rentals in Ashland
Kid Friendly Ashland Holiday Rentals
Romantic Ashland Holiday Rentals
Downtown Ashland Holiday Rentals
Holiday Rentals near Emigrant Lake
Shopping
Package Holidays
Cruises
Car Hire
Tours
Add a Place
Travel Forum
Airlines
Best of 2022
Help Centre
Travel Articles
Cottages, Villas, Apartments in Ashland
Holiday Rentals
USA
Oregon (OR)
Cottages, Villas, Apartments in Ashland
Search
Ashland Holiday Rentals
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Parking (200)
Internet (197)
Other outdoor space (151)
Air Conditioning (149)
Show more
Suitability
Kid friendly (169)
Business Travel (47)
Pet friendly (32)
Elder access (28)
Show more
Property type
Holiday Rental House (151)
Condominium/Apartment (46)
Cabin Holiday Rental (11)
Private Room (0)
Show more
Distinctive Features
Mountain Views (7)
Housekeeping Included (2)
Private Chef (0)
Private Beach (0)
Show more
Distance from
1 mi
208 rentals
in Ashland.
Sort by:
Tripadvisor Sort
#32 & #33 Hyatt Prairie Compound - Hot Tub- Sleeps 12- Kitchen
Cabin Holiday Rental
4 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
The Ashland Cottage, walk to town
139 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Craftsman Style Home In Country Setting
121 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Brand New Custom Ashland Home with Fantastic Mountain Views
47 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Steps to theatres, restaurants, shops, nightlife in historic railroad district
111 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland
50 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Hanna's House- Your Home Away from Home
111 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Railroad District, steps to downtown, everything you need to enjoy Ashland!
78 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Madrone House, New Country Getaway with Panoramic Views
48 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248)
100 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Save time - get the best
Ashland
rentals sent straight to your email!
Get the List
High Street Cottage Artists' Garden Cottage Clean & Beautiful
49 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Maple Apartment at Tudor House Vacation Rentals
107 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Hyatt Lake Mountain Retreat
36 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Hyatt Praire Mountain Cabin
24 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
ArtYcottage UNBELIEVEABLE...
19 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Asian Inspired Escape with View - Just 3 Miles from Downtown
45 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub
27 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Perfect Vacation Cottage
63 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Aloha House ~ Hot Tub & Seasonal Pool
20 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
'Orchard Suite' Stay...Relax...Enjoy
41 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
62 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
72 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland
41 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!
25 reviews
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
27 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
37 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Terra Cottage Inn a beautiful Luxury Apartment
11 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Helman House-Three Blocks from the Oregon Shakespeare Festival
38 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Big Discounts 2020! Walk to town from this Charming Cottage.
88 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Winter on PINE STREET! ASHLAND! COZY cottage near Lithia Park and Town!
19 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Pioneer - Craftsman House - Closest to OSF!
37 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Charming Space Next to Everything, Walk Anywhere!
20 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Welcome to clean air, space and relaxation in SE Ashland!
57 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Mt. Ashland Homestead's Secluded Forest House, 15 minutes from Ashland
19 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Quiet and peaceful cottage close to downtown
24 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Private Suite Near Shakespeare
42 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Dogwood Suite at Tudor House Vacation Rentals
75 reviews
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
36 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Zen Atmosphere Studio Cottage. Private Entrance & Healing Garden. Walk to Plays
36 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
8 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Whispering Pines Cabin Retreat ~ Dog Friendly
20 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Charming, Comfortable Garden Studio Above The University.
17 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Ashland Cabin - 170 Acres w/Mountain Views & Sauna
25 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The High Street Cottage An Artists' Garden Cottage
7 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Hyatt Prairie Mountain Cabin
34 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
ArtYCottage - custom furniture and art through out. Secluded and fabulous!
47 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
#44 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub
24 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
2 bedroom, Modern, Up Scale House, Walk to Town
48 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
#46 The Cabins at Hyatt Lake-Sleeps 5-Dog Friendly
18 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
The Pioneer House -North Suite (Upstairs) - Closest to OSF!
19 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Previous
Next
1
2
3
4
5
Frequently Asked Questions about Ashland
Do any holiday rentals in Ashland have a pool?
Yes, here are some popular holiday rentals in Ashland that have a pool:\n
\n
The Aloha House ~ Hot Tub & Seasonal Pool
\n
The Aloha House ~ Hot Tub & Seasonal Pool
\n
Gorgeous Views! Stratford Inn Hotel in Ashland Oregon | Affordable Extended Stay
\n
\n
See all holiday rentals with a pool in Ashland on Tripadvisor
Do any holiday rentals in Ashland have internet access?
Yes, here are some popular holiday rentals in Ashland that have internet access:\n
\n
ArtYcottage UNBELIEVEABLE...
\n
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
\n
The High Street Cottage An Artists' Garden Cottage
\n
\n
See all holiday rentals in Ashland on Tripadvisor
What are the best pet friendly rentals in Ashland?
The best pet friendly rentals in Ashland are:\n
\n
ArtYcottage UNBELIEVEABLE...
\n
Cattle View Ranch House
\n
Carlisle Garden Suites - Calla Suite
\n
\n
See all pet friendly holiday rentals in Ashland on Tripadvisor
What are some great rentals in Ashland that are kid friendly?
Some of the most popular kid friendly rentals in Ashland are:\n
\n
ArtYcottage UNBELIEVEABLE...
\n
Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
\n
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland
\n
\n
See all kid friendly holiday rentals in Ashland on Tripadvisor