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Ashland, OR place to stay
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301 Lodgings in Ashland, OR

Best family friendly Ashland, OR lodging

Among the 301 accommodations in Ashland, OR, here are the 4 best for families

1907 Charmer, Perfect Downtown Location, So Clean! - Ashland, OR
9.5 187 reviews
Ashland, OR
20/06 – 23/06
₹52979/nighttotal: ₹158937 (3 )

1907 Charmer, Perfect Downtown Location, So Clean!

1 5
apartment , Ashland
This house is located in Ashland's Historic Downtown District, just 0.5km from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The 3-bedroom house spans 118 square metres and features a fully equipped kitchen, two bathrooms, a washing machine, and a garden. Guests can enjoy amenities such as air conditioning, parking, and a spa, making it ideal for a comfortable and relaxing stay.
The Ashland Social | Guest Studio - Ashland, OR
10 26 reviews
Ashland, OR
17/09 – 23/09
₹22607/nighttotal: ₹135642 (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.
Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.4 10 reviews
Ashland, OR
05/09 – 07/09
₹34539/nighttotal: ₹69078 (2 )

Charming House Two Blocks From Downtown Ashland

2 2
apartment , Ashland
The Serendipity House, a newly remodelled two-bedroom property, is centrally located in Ashland, Oregon, just 0.32 kilometres from restaurants, shops, and theatres, offering easy access to the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
This self-catering house sleeps four guests and boasts a full kitchen with complimentary coffee, a spacious living room, a private garden, parking, and air conditioning, plus it's ideally situated for exploring North Mountain Park and the Rogue River-Siskiyou National Forest.
1 King Bed 1 Queen Bed 2 Bedroom House With Ac, Wifi And Washer And Dryer - Ashland, OR
10 24 reviews
Ashland, OR
19/06 – 20/06
₹34365/nightfor 1 night

1 King Bed 1 Queen Bed 2 Bedroom House With Ac, Wifi And Washer And Dryer

2 1
apartment , Medford
This Medford holiday home is conveniently located less than 1 km from Alba Park and Medford City Hall, and within 1.5 km of Medford Carnegie Library and Fichtner-Mainwaring Park.
The 116 square metre property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, swimming pool, patio, and free Wi-Fi.

Best Ashland, OR lodging with a pool

Among the 301 accommodations in Ashland, OR, here are the 4 best ones with a pool

The R & R - Ashland, OR
10 4 reviews
Ashland, OR
20/06 – 27/06
₹63725/nighttotal: ₹446075 (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.
Mountainside Chateau Spectacular Views And Sunsets. 15 Min To Downtown Ashland! - Ashland, OR
9.6 16 reviews
Ashland, OR
02/07 – 06/07
₹140757/nighttotal: ₹563028 (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.
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You! - Ashland, OR
9.8 30 reviews
Ashland, OR
17/09 – 23/09
₹92578/nighttotal: ₹555468 (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.
The Carriage House, Winner 2025 Best Of Ashland! - Ashland, OR
9.8 277 reviews
Ashland, OR
17/09 – 23/09
₹21860/nighttotal: ₹131160 (6 )

The Carriage House, Winner 2025 Best Of Ashland!

1 2
apartment , Ashland
This one-bedroom flat is situated in Ashland's Historic Downtown District, just 0.8km from the Oregon Shakespeare Festival, making it perfect for exploring the area's cultural offerings. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The self-catering apartment is located on the upper floor of a garage, offering privacy and a separate space from the main house, and can accommodate up to four guests. The flat includes a fully equipped kitchen, air conditioning, a shared swimming pool, and a garden, perfect for a relaxing stay.

Frequently asked questions about accommodations in Ashland, OR

  • What are the must-see sites in or near Ashland, OR?

    Ashland is a real gem, and you've got to see the Oregon Shakespeare Festival, it's world-renowned. The historic Lithia Park is a must-visit, it's stunning. If you're into nature, the nearby Rogue River is a must-see, it's beautiful.
  • How can travelers reach Ashland, OR?

    The easiest way to get to Ashland is by flying into the Medford Airport, about 20 minutes away. If you're driving, you can take Interstate 5, and it's about a 3-hour drive from Portland or a 6-hour drive from San Francisco.
  • What outdoor activities can visitors enjoy in and around Ashland, OR?

    Hiking is a big thing here, there are lots of trails around, like the Siskiyou Mountains. You can also go kayaking on the Rogue River, it's a real treat. If you're looking for something more relaxed, there's the Ashland Botanical Gardens, it's a beautiful place to wander around.
  • When is the ideal time to plan a trip to Ashland, OR?

    The best time to visit Ashland is during the summer, from June to August, the weather is perfect. If you're into theatre, the Oregon Shakespeare Festival runs from February to October, so you can catch a show during that time. Spring and autumn are also lovely, but it can be a bit rainy.
  • What are the best walking or cycling routes in Ashland, OR?

    The Lithia Park Loop is a great walking or cycling route, it's about 4 km long and goes around the park. If you're feeling adventurous, you can try the Bear Creek Greenway, it's a 10 km paved trail that goes along Bear Creek.
  • What nearby towns or cities can be explored from Ashland, OR?

    There are loads of places to visit nearby. Medford is just a short drive away, and it's got a cool downtown area. If you want to head to the coast, you can go to Gold Beach, it's about a 2-hour drive. And if you're into wine, you can visit the wineries in the Applegate Valley, it's about 30 minutes away.
  • What amenities can travelers expect from accommodations in Ashland, OR?

    Ashland has a good range of accommodation options, from budget-friendly motels to luxurious hotels. Most places will have Wi-Fi, parking, and breakfast. Some places even have swimming pools or hot tubs.

Destinations nearby

Best Ashland, OR accommodations with a garden

Hanna's House By Wanderlodges - Ashland, OR
9.8 11 reviews
Ashland, OR
08/08 – 10/08
₹39025/nighttotal: ₹78050 (2 )

Hanna's House By Wanderlodges

1 4
house , Ashland
Hanna's House offers a self-catering property in Ashland, Oregon, conveniently located a short walk from the Oregon Shakespeare Festival and Oregon Cabaret Theatre, and within easy reach of the Schneider Museum of Art (1.9km) and Oak Knoll Golf Course (5.6km).
This 165 square metre house sleeps seven guests and boasts a well-equipped kitchen, private parking, Wi-Fi, a terrace, garden, and air conditioning; nearby activities include fishing, canoeing, hiking, skiing, golfing, and cycling.
Craftsman Cottage Built In 2019 - Ashland, OR
9.6 557 reviews
Ashland, OR
20/06 – 23/06
₹15082/nighttotal: ₹45246 (3 )

Craftsman Cottage Built In 2019

1 5
apartment , Phoenix
This craftsman-style Airbnb is situated in a peaceful neighbourhood in Phoenix, just a short drive from the city's main attractions. The property has received excellent ratings for its cleanliness, location and overall experience.
The home has two bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a spacious garden, air conditioning, parking, and free internet access, making it ideal for a relaxing and comfortable stay.
Lighthouse-themed, Fastest Wifi, 2 King Beds Home - Ashland, OR
9.8 58 reviews
Ashland, OR
20/06 – 23/06
₹31310/nighttotal: ₹93930 (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.
Siskiyou Chateau - Ashland, OR
9.7 30 reviews
Ashland, OR
02/07 – 06/07
₹127986/nighttotal: ₹511944 (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).

Best Ashland, OR accommodations with a kitchen

Hot Tub | Sauna |Firepit |Sleeps 6! - Ashland, OR
10 5 reviews
Ashland, OR
20/06 – 21/06
₹59533/nightfor 1 night

Hot Tub | Sauna |Firepit |Sleeps 6!

2 4
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.
The Dogwood Suite At Tudor House Vacation Rentals - Ashland, OR
9.4 200 reviews
Ashland, OR
08/08 – 10/08
₹27503/nighttotal: ₹55006 (2 )

The Dogwood Suite At Tudor House Vacation Rentals

1 4
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.
Peace And Joy Mini Farm - Ashland, OR
9.4 204 reviews
Ashland, OR
17/09 – 23/09
₹14876/nighttotal: ₹89256 (6 )

Peace And Joy Mini Farm

2 2
gîte , Ashland
This Ashland countryside self-catering property is located 5 minutes (approximately 8km) from Ashland's town centre, providing easy access to the Oregon Shakespeare Festival and within a short drive of Mount Ashland Ski Area.
This pet-friendly holiday home offers two bedrooms, one bathroom, sleeping up to four guests, and features a mini-farm, BBQ area, on-site beauty salon, free parking, and excellent guest reviews.
Oak Lawn Cottage - Ashland, OR
9.8 85 reviews
Ashland, OR
20/06 – 21/06
₹39042/nightfor 1 night

Oak Lawn Cottage

2 4
apartment , Ashland
This charming cottage is situated just a short walk from Ashland's lively downtown, where you can find theatres, restaurants and art galleries. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cottage comfortably sleeps up to six guests in its two bedrooms and one bathroom. Enjoy relaxing evenings by the fireplace, cook meals in the fully equipped kitchen and dine al fresco on the private porch and garden.
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