Beautiful Guest Suite With Private Deck Overlooking Forest And Waterfall
1 2
apartment , Ashland
This one-bedroom apartment is located in Ashland, just 5km from Weisinger Family Winery, Southern Oregon University, and Schneider Museum of Art, making it a convenient base for exploring the city's cultural attractions. It has received excellent user ratings, so you can be sure of a comfortable stay. The 42 square metre apartment comfortably sleeps two guests and has a fully equipped kitchen, a private patio, and a garden. You'll also enjoy the use of a spa, parking, and free Wi-Fi.
9.5 12 reviews
Ashland, OR
17/09 – 23/09
SG$151/nighttotal: SG$906 (6 )
Beautiful Ashland Flat
1 2
apartment , Ashland
This Ashland apartment, ideally located for exploring the city, offers a private upstairs unit with independent access. The one-bedroom self-contained flat sleeps two guests, boasts a fully equipped kitchen with modern appliances, a private deck, and includes high-speed Wi-Fi and all utilities.
This three-bedroom house, sleeping six, is situated in Ashland's Historic Railroad District, within 1.6km of the Ashland Library, Oregon Cabaret Theatre, Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre. The property offers free Wi-Fi, a fully equipped kitchen with fridge, microwave, and dishwasher, a garden, parking, and is within easy walking distance of various attractions, making it ideal for families or groups visiting Ashland.
9.9 32 reviews
Ashland, OR
17/09 – 23/09
SG$820/nighttotal: SG$4920 (6 )
Ashland Lavender Estate
1 2
gîte , Ashland
This farmhouse rental is situated just a few kilometres from the centre of Ashland, Oregon, offering a peaceful escape from the town's bustle while still being close to its attractions. The property has received excellent ratings for location, cleanliness, and overall guest experience. The farmhouse comfortably sleeps eight guests in its four bedrooms and three bathrooms. Guests can enjoy a private swimming pool, hot tub, bocce ball court, fire pit, and pond with a waterfall, along with a fully equipped kitchen and a cosy living room with a fireplace.
Ashland, OR
02/07 – 06/07
SG$470/nighttotal: SG$1880 (4 )
Cozy Santa Feinspired 2br Retreat With Queen Beds, Sofa Sleeper, Soaking Tub, Fireplace, And Large Fenced Backyard. Great Location Near Medford, Jacksonville Wineries, And Ashland.
3 5
apartment , Medford
This Santa Fe-style flat in Medford offers a central location, placing you 800 metres from the Craterian Theater at The Collier Center, 8 kilometres from Historic Jacksonville, and 19 kilometres from the Oregon Shakespeare Festival in Ashland. This three-bedroom, one-bathroom dwelling spans 89 square metres, accommodates up to six guests, and features a fully stocked kitchen, a lounge with a fireplace, and a secure garden, with parking and Wi-Fi provided.
9.7 30 reviews
Ashland, OR
02/07 – 06/07
SG$1724/nighttotal: SG$6896 (4 )
Siskiyou Chateau
1 5
apartment , Ashland
Siskiyou Chateau, near Emigrant Lake in the Rogue Valley, offers a luxurious stay a short drive from Ashland, Oregon. This five-bedroom, four-bathroom property sleeps twelve guests and boasts a gourmet kitchen, swimming pool, hot tub, and extensive outdoor entertaining areas, including a wood-fired pizza oven (seasonal).
10 177 reviews
Ashland, OR
17/09 – 23/09
SG$225/nighttotal: SG$1350 (6 )
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
1 2
house , Ashland
This French Country style villa is located on the outskirts of Ashland, offering a peaceful retreat on three acres of land while still being just a short distance from the town's restaurants, shops, and attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. The villa is a single-storey property with a floor area of 186 square metres. Amenities include a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, parking, and a rec room with a sofa bed, ensuring a comfortable and enjoyable stay for guests.
10 61 reviews
Ashland, OR
02/07 – 06/07
SG$640/nighttotal: SG$2560 (4 )
Meadow House At Willow-witt Ranch (Farm Stay)
1 5
gîte , Ashland
The Meadow House self-catering cottage is located in the Southern Cascades near Willow-Witt Ranch, at an altitude of approximately 1524 metres, its precise distance from Ashland unspecified. This three-bedroom, two-bathroom property sleeps up to eight guests, offering Wi-Fi, a well-equipped kitchen (including farm-fresh produce), a garden, parking, and access to hiking trails; children under three stay free, and farm activities are available.
9.9 47 reviews
Ashland, OR
02/07 – 06/07
SG$1689/nighttotal: SG$6756 (4 )
The Gem & Cottage, Pool, Hot Tub, Views
5 5
house , Talent
This hilltop residence in Talent offers magnificent mountain views and sunsets, situated just 7 kilometres from downtown Ashland and the Oregon Shakespeare Festival. This expansive five-bedroom, four-bathroom property accommodates fourteen guests, featuring a swimming pool, hot tub, copper cold plunge, chef's kitchen, home theatre, and a private studio loft with a kitchenette.
10 5 reviews
Ashland, OR
25/06 – 26/06
SG$802/nightfor 1 night
Hot Tub | Sauna |Firepit |Sleeps 6!
2 3
apartment , Ashland
This luxurious Ashland apartment, close to Lithia Park and the Oregon Shakespeare Festival, offers easy access to wineries such as Grizzly Peak and Weisinger Family, and is within a few kilometres of hiking and mountain biking trails. The two-bedroom property, sleeping up to six guests with a pull-out sofa bed and boasting three bathrooms, features a gourmet kitchen with wine fridge, hot tub, sauna, outdoor fire pit, and a terrace with sweeping valley views; a 20% discount on Oregon Shakespeare Festival B and C section tickets is also included.
9.4 200 reviews
Ashland, OR
05/09 – 07/09
SG$308/nighttotal: SG$616 (2 )
The Dogwood Suite At Tudor House Vacation Rentals
1 2
apartment , Ashland
This apartment is situated in the Siskiyou-Hargadine Historic District, just 1.5 kilometres from Southern Oregon University, Ashland Library, and the Oregon Cabaret Theatre, and less than 1.6 kilometres from the Oregon Shakespeare Festival and Thomas Theatre. It has consistently received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, two-bathroom flat spans 74 square metres and comfortably accommodates up to five guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, and free Wi-Fi in public areas, along with a washing machine, a TV and DVD player, and air conditioning.
9.9 179 reviews
Ashland, OR
20/06 – 23/06
SG$583/nighttotal: SG$1749 (3 )
Galaxy-themed, Fastest Wifi, 3 King Beds Home
2 5
apartment , Medford
This house is located just 3 kilometres from 2Hawk Vineyard & Winery, Asante Rogue Regional Medical Center, and Centennial Golf Club, making it a convenient base for exploring Medford. It has received excellent ratings for location, cleanliness, and overall user experience. This property can accommodate up to 6 guests and features 3 bathrooms, a washing machine, free WiFi, and a dining area. Enjoy the convenience of a fully equipped kitchen, a fitness centre, a spa tub, and a terrace or balcony overlooking the garden.
Best family friendly Ashland, OR lodging
Among the 301 accommodations in Ashland, OR, here are the 4 best for families
10 5 reviews
Ashland, OR
05/09 – 07/09
SG$1019/nighttotal: SG$2038 (2 )
Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen
2 2
apartment , Ashland
This Queen Anne-style holiday home in Ashland, Oregon, is situated less than 1.6km from the downtown area, offering easy access to shops, theatres, and restaurants. The 500 square metre property boasts two bedrooms, one bathroom with a luxurious soaking tub and walk-in shower, a full kitchen including a gas stove and grill, three off-street parking spaces, a fully fenced garden, and can comfortably accommodate four guests.
9.8 58 reviews
Ashland, OR
20/06 – 23/06
SG$422/nighttotal: SG$1266 (3 )
Lighthouse-themed, Fastest Wifi, 2 King Beds Home
1 5
house , Medford
This Medford ground-floor condo, ideal for families, offers ADA-friendly access and is conveniently located within Medford (precise location unspecified, requiring further details on proximity to local landmarks). The 2-bedroom, 2-bathroom apartment sleeps up to 6 guests, featuring king-sized beds, a sleeper sofa, a well-equipped kitchen with family-friendly provisions, and a 24/7 monitored security system; further details on the property's size and specific amenities are needed.
10 26 reviews
Ashland, OR
17/09 – 23/09
SG$304/nighttotal: SG$1824 (6 )
The Ashland Social | Guest Studio
1 2
studio , Ashland
This studio apartment is located just 0.4 kilometres from Ashland Plaza, placing you within easy reach of the city's main attractions, restaurants, and shops. It has received excellent user ratings, making it a popular choice for travellers. The apartment has a private entrance and can comfortably accommodate two guests. It features a kitchenette with a fridge, microwave, and other appliances, as well as Wi-Fi, heating, and parking.
9.7 56 reviews
Ashland, OR
17/09 – 23/09
SG$608/nighttotal: SG$3648 (6 )
Barclay Klum House | Soaking Tub & Gourmet Kitchen
1 2
apartment , Ashland
This Queen Anne-style apartment in Ashland, Oregon, is located less than 1.6 km from Ashland's downtown area, offering easy access to shops, theatres, and parks. The property, sleeping four guests, boasts a well-equipped kitchen with a European gas stove and electric convection oven, two bedrooms (one queen, one double), a bathroom with a soaking tub and walk-in shower, private off-street parking, and a fenced yard.
Best Ashland, OR lodgings with a pool
Among the 301 accommodations in Ashland, OR, here are the 4 best ones with a pool
10 4 reviews
Ashland, OR
20/06 – 27/06
SG$858/nighttotal: SG$6006 (7 )
The R & R
4 2
apartment , Talent
This holiday home is situated in Southern Oregon, a 5-minute drive from downtown Ashland, offering convenient access to multiple lakes, hiking trails, and local wineries. This expansive 743 square meter property boasts four bedrooms, two bathrooms, and capacity for ten guests, featuring a heated swimming pool, a gourmet kitchen with a six-burner gas range and two ovens, a formal dining room, and ample parking for an RV.
9.1 2280 reviews
Ashland, OR
25/06 – 26/06
SG$1169/nightfor 1 night
Lithia Springs Resort
2 3
resort , Ashland
Lithia Springs Resort is located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, offering easy access to the area's cultural attractions. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience. The resort features a range of accommodation options, including suites and bungalows, all decorated in a modern spa-themed style. Guests can enjoy a variety of amenities, including mineral spring water soaking bathtubs, a seasonal outdoor saltwater pool, a hot tub, and a complimentary full breakfast.
9.6 16 reviews
Ashland, OR
02/07 – 06/07
SG$1896/nighttotal: SG$7584 (4 )
Mountainside Chateau Spectacular Views And Sunsets. 15 Min To Downtown Ashland!
5 5
apartment , Ashland
This five-bedroom holiday home in Ashland offers a mountain and lakefront setting, located a short drive from Southern Oregon University, the Oregon Cabaret Theatre, and the Oregon Shakespeare Festival. Spanning 492 square meters, this spacious property accommodates up to ten guests and features a fully equipped kitchen, a balcony for alfresco dining, complimentary Wi-Fi, and is close to outdoor pursuits such as hiking and kayaking.
9.8 30 reviews
Ashland, OR
17/09 – 23/09
SG$1247/nighttotal: SG$7482 (6 )
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You!
4 2
farm , Ashland
This farm stay is located just a few kilometres from downtown Ashland, near the Oregon Shakespeare Festival and a range of restaurants, offering a peaceful escape from the city. It has received excellent user ratings, highlighting its high standards. The farmhouse spans 269 square metres and comfortably accommodates up to 10 guests. It boasts a large in-ground pool, a hot tub, a chef's kitchen, and a variety of recreational activities, including bocce ball, basketball, and a pond with a pergola and swing.
Frequently asked questions about accommodations in Ashland, OR
What are the must-see sites in or near Ashland, OR?
Ashland is full of things to see! You definitely want to check out the Oregon Shakespeare Festival, a world-renowned theatre company. The Lithia Park is a beautiful spot right in the heart of town, with a stunning waterfall. And for stunning scenery, drive up to the top of Mount Ashland for panoramic views of the Rogue Valley.
The easiest way to get to Ashland is by flying into the Medford Rogue Valley International Airport, which is about 20 minutes away. You can also drive, as Ashland is located off Interstate 5. If you're feeling adventurous, you can take Amtrak's Coast Starlight train, which stops in nearby Klamath Falls.
What are the best accommodations with a pool in Ashland, OR?
What outdoor activities can visitors enjoy in and around Ashland, OR?
Ashland is a great base for outdoor adventures! You can hike to the top of Mount Ashland, go fishing in the Rogue River, or explore the Siskiyou Mountains on a scenic drive. There are also plenty of trails for mountain biking and horseback riding.
What are the best accommodations with a jacuzzi in Ashland, OR?
When is the ideal time to plan a trip to Ashland, OR?
The best time to visit Ashland is during the summer, when the weather is warm and sunny. The Oregon Shakespeare Festival is in full swing during this time, so you can enjoy a variety of performances. If you're looking for a quieter experience, spring or autumn are also good times to visit.
What are the best accommodations for families and kids in Ashland, OR?
What are the best walking or cycling routes in Ashland, OR?
The Lithia Park Loop Trail is a great option for a leisurely walk or bike ride. It's a 2.5 km paved loop that winds through the park, offering stunning views of the Rogue River and the surrounding mountains. For a more challenging ride, try the Bear Creek Greenway, which stretches for 16 km along the Bear Creek.
What are the best pet friendly accommodations in Ashland, OR?
What nearby towns or cities can be explored from Ashland, OR?
You can easily take a day trip from Ashland to nearby Medford, which is about 20 minutes away. Medford has a charming downtown area with shops and restaurants, and it's also home to the Rogue Valley Mall. Another option is to drive to Jacksonville, a historic gold rush town that's about 30 minutes away.
What are the best accommodations with parking in Ashland, OR?
What amenities can travelers expect from accommodations in Ashland, OR?
Ashland offers a wide range of accommodation options, from budget-friendly motels to luxurious hotels. Many accommodations offer amenities like swimming pools, hot tubs, and fitness centres. You can also find places with kitchens, laundry facilities, and free Wi-Fi.
Destinations nearby
Best Ashland, OR accommodations with a garden
10 55 reviews
Ashland, OR
20/06 – 21/06
SG$667/nightfor 1 night
Plaza North Suite 203 Windsor
1 4
apartment , Ashland
This luxury Ashland condo is situated in the downtown area, within easy walking distance of the Oregon Shakespeare Festival venues and close to the culinary and shopping districts. The one-bedroom apartment, sleeping up to four guests, boasts a spacious great room with a state-of-the-art fireplace, a private balcony offering Ashland hills views, a fully equipped modern kitchen, and covered parking with adjacent EV charging points.
Ashland, OR
05/09 – 07/09
SG$783/nighttotal: SG$1566 (2 )
Hanna's House By Wanderlodges
1 2
house , Ashland
This cottage is located 1 kilometre from Ashland's city centre, offering easy access to the Ashland Library, Oregon Cabaret Theatre, and Lithia Park. This property accommodates two guests and features a kitchen with a dishwasher, air conditioning, a garden, an on-site restaurant, and parking, with Wi-Fi provided and laundry services available.
10 36 reviews
Ashland, OR
02/07 – 06/07
SG$686/nighttotal: SG$2744 (4 )
"Enchantment" Jacksonville, Oregon
4 5
apartment , Medford
This Medford property, a spacious four-bedroom house, is situated 19 kilometres north of Ashland and 11 kilometres south of Jacksonville, offering easy access to the Oregon Shakespeare Festival and Britt Festival. The 251-square-metre dwelling boasts a jacuzzi, terrace, garden, and parking, accommodating eight guests with amenities including a fully equipped kitchen, Wi-Fi, and access to nearby attractions such as the Beekman House and Craterian Ginger Rogers Theatre.
9.4 3 reviews
Ashland, OR
05/09 – 07/09
SG$1969/nighttotal: SG$3938 (2 )
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.
4 2
apartment , Ashland
This six-bedroom apartment, sleeping up to twelve guests, is situated in Ashland's Siskiyou-Hargadine Historic District, within a 1.6km walk of the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library. The 260 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, terrace, parking, and free Wi-Fi; nearby attractions include the Angus Bowmer Theatre and Thomas Theatre, both within 1.6km.
Best Ashland, OR accommodations with a kitchen
8.8 3 reviews
Ashland, OR
05/09 – 07/09
SG$487/nighttotal: SG$974 (2 )
Swank Suites | Step Free King
1 2
apartment , Ashland
This first-floor apartment in Ashland's historic Railroad District is situated one block from a grocery store and coffee shop, two blocks from an escape room, and within easy walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens. The 37-square-metre (approximately 398 square feet) flat offers a king-size bed, a kitchenette, a private outdoor lounge, shared laundry facilities, high-speed 5G internet, a 65-inch smart TV with Netflix, and accommodates two guests; parking is also available.
10 2 reviews
Ashland, OR
20/06 – 27/06
SG$266/nighttotal: SG$1862 (7 )
Gorgeous Log Cabin With Sauna
1 2
apartment , Talent
This restored 1920s log cabin offers a unique rural setting amongst wineries, just 3.2 kilometres from downtown Ashland and its Shakespeare Festival. This pet-friendly holiday let sleeps four guests and features two bathrooms, a kitchen with a fridge and microwave, air conditioning, and access to seven wooded acres with walking trails and communal outdoor areas.
9.8 66 reviews
Ashland, OR
05/09 – 07/09
SG$355/nighttotal: SG$710 (2 )
Quiet And Peaceful Cottage Close To Downtown
1 2
apartment , Ashland
This apartment is located in Ashland's Siskiyou-Hargadine Historic District, a mere 500 meters from downtown Ashland, offering convenient access to its shops, restaurants, and cultural attractions. This 93 square meter, two-storey property accommodates up to five guests, featuring a full kitchen, a pullout sofa bed, a suite with a queen bed, and a private outdoor space, with off-street parking provided.
9.8 10 reviews
Ashland, OR
05/09 – 07/09
SG$574/nighttotal: SG$1148 (2 )
Luxury Condo With King Bedroom, Two Bathrooms, Full Kitchen.
1 2
chalet , Ashland
This luxury apartment in Ashland's Historic Downtown District is located steps from restaurants and shops, and a short walk from the Oregon Shakespeare Festival venues. The 100-square-metre (1076 square-foot) condo boasts a king bedroom, two bathrooms, a fully equipped kitchen, and a spacious great room with a fireplace, accommodating up to four guests and offering stunning Ashland Hills views from a private balcony; secure parking and elevator access are also provided.