Holiday Rentals in Ashland, OR

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Ashland, OR holiday rentals
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203 Holiday Rentals and Airbnb in Ashland, OR

Best family friendly Ashland, OR holiday rentals

Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals

Lithia Springs Resort - Ashland, OR
9.1 2281 reviews
Ashland, OR
07/10 – 12/10
NZ$1072/nighttotal: NZ$5360 (5 )

Lithia Springs Resort

2 4
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.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.6 4 reviews
Ashland, OR
07/10 – 12/10
NZ$2227/nighttotal: NZ$11135 (5 )

Luxury Ashland Mountain Escape: Pool, Hot Tub

4 4
house , Ashland
This waterfront villa near Ashland, Oregon, is located 1.4 kilometres from Weisinger Family Winery and 4.8 kilometres from Southern Oregon University.
The 353-square-metre property boasts four bedrooms, four bathrooms, and sleeps twelve guests, offering a private pool, hot tub, barbecue grills, and a fully equipped kitchen including a dishwasher; laundry facilities are also provided.
Centrally Located Downtown Historic Home W/parking - Ashland, OR
9.7 43 reviews
Ashland, OR
20/08 – 22/08
NZ$924/nighttotal: NZ$1848 (2 )

Centrally Located Downtown Historic Home W/parking

1 2
apartment , Ashland
This Ashland, Oregon house, built in 1887, is centrally located, within walking distance of Ashland's downtown area and a short distance (less than 1.6km) from Lithia Park.
Sleeping six guests across three bedrooms and one bathroom, this property offers a well-equipped kitchen, air conditioning, parking, internet access, and pet-friendly facilities.
Barclay Klum House | Soaking Tub & Gourmet Kitchen - Ashland, OR
9.7 56 reviews
Ashland, OR
20/08 – 22/08
NZ$828/nighttotal: NZ$1656 (2 )

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 holiday rentals with parking

Peaceful 1-bedroom Bungalow With Ac In Charming Ashland - Ashland, OR
10 9 reviews
Ashland, OR
18/09 – 20/09
NZ$587/nighttotal: NZ$1174 (2 )

Peaceful 1-bedroom Bungalow With Ac In Charming Ashland

1 2
apartment , Ashland
This one-bedroom flat is located just 100 metres north of Ashland's downtown plaza, offering convenient walking access to the Oregon Shakespeare Festival, Oregon Cabaret Theatre, shops, restaurants, Lithia Park, and the Japanese Garden.
The 46 square metre bungalow accommodates two guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a private patio and garden, and is ideal for those interested in mountain climbing, hiking, and mountain biking.
Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen - Ashland, OR
10 5 reviews
Ashland, OR
18/09 – 20/09
NZ$1099/nighttotal: NZ$2198 (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.
Swank House -Downtown Suite- Pet Friendly - Ashland, OR
10 7 reviews
Ashland, OR
04/08 – 06/08
NZ$451/nighttotal: NZ$902 (2 )

Swank House -Downtown Suite- Pet Friendly

1 2
apartment , Ashland
This Ashland apartment, situated in the Historic Railroad District, is steps from downtown and within easy walking distance of the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
The 35-square-metre (377 sq ft) self-catering flat offers a king-size bed, private parking, a patio (June-October), and accommodates two guests, with a microwave, air conditioning, and Wi-Fi included; one pet is permitted.
Meadowsweet Farm | Hot Tub, Outdoor Kitchen - Ashland, OR
10 2 reviews
Ashland, OR
07/10 – 12/10
NZ$1688/nighttotal: NZ$8440 (5 )

Meadowsweet Farm | Hot Tub, Outdoor Kitchen

7 4
apartment , Talent
This restored farmhouse, situated in Medford, is a mere 700 metres from Paschal Winery and StoneRiver Vineyards, offering a distinctive wine country escape with easy access to downtown Medford's attractions.
This family-friendly property accommodates up to 18 guests across 7 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a garden with an outdoor kitchen and fireplace, and parking, making it ideal for large groups seeking a comfortable stay.

Frequently asked questions about holiday rentals in Ashland, OR

  • What are some interesting places to visit in or near Ashland, OR?

    Ashland is home to the Oregon Shakespeare Festival, a world-renowned theatre company. You can also visit the Lithia Park, a beautiful park with a Japanese Garden and a stunning waterfall. For a day trip, drive to the nearby Crater Lake National Park, a breathtaking volcanic caldera with stunning views.
  • What are the best Airbnb and holiday rentals in Ashland, OR?

  • Which walking or cycling routes are the best in Ashland, OR?

    The Ashland Greenway is a popular paved path that runs along the Bear Creek, great for walking or cycling. For a more challenging ride, try the Emigrant Trail, which winds through the foothills of the Siskiyou Mountains. If you're into mountain biking, there are plenty of trails in the surrounding forests.
  • What are the most popular Airbnbs in Ashland, OR?

  • What sports or outdoor activites can visitors enjoy in and around Ashland, OR?

    Ashland is a great place for hiking, with trails ranging from easy strolls to challenging climbs. You can go fishing in the Rogue River or go kayaking on the lake. In the winter, there are opportunities for skiing and snowboarding at nearby resorts like Mount Ashland Ski Area.
  • What are the best holiday rentals with a pool in Ashland, OR?

  • What other towns or cities can be easily accessed from Ashland, OR?

    You can easily drive to Medford, the largest city in the region, which has a regional airport and a variety of shopping and dining options. Jacksonville, a historic gold rush town, is about 30 minutes away. For a longer drive, you can visit Crater Lake National Park, about 2 hours away.
  • What are the best rentals for families and kids in Ashland, OR?

  • What amenities are commonly available in vacation rentals in Ashland, OR?

    Most vacation rentals in Ashland offer basic amenities like kitchens, bathrooms, and bedrooms. Many also have laundry facilities, Wi-Fi, and outdoor spaces like patios or balconies. Some rentals may also have amenities like hot tubs, fireplaces, or even private pools.
  • What are the best rentals or Airbnbs with a jacuzzi in Ashland, OR?

  • What time of year is best to rent a vacation rental Ashland, OR?

    The best time to visit Ashland depends on your interests. Summer is popular for the Oregon Shakespeare Festival and outdoor activities, while autumn offers beautiful foliage and cooler temperatures. Spring is a good time for hiking and wildflowers, and winter is ideal for snow sports.
  • What are the local dishes in Ashland, OR region?

    Ashland is known for its farm-to-table cuisine, with many restaurants featuring fresh, local ingredients. Some popular local dishes include trout, wild mushrooms, and berries. You can also find delicious craft beers and wines produced in the region.

Destinations nearby

Best Ashland, OR holiday rentals with a balcony

Lithia Springs Resort - Ashland, OR
Ashland, OR
03/07 – 06/07
NZ$616/nighttotal: NZ$1848 (3 )

Lithia Springs Resort

1 2
resort , Ashland
Lithia Springs Resort is located in Ashland, Oregon, 4 kilometres from the city centre, offering convenient access to Ashland's attractions.
This hotel boasts a spa, indoor and outdoor swimming pools, a fitness centre, and various business facilities including a conference hall, alongside a bar, library, and picnic area, ensuring a comfortable stay.
Chateau Herbe ~ Oberon Suite W/ Kitchen - Ashland, OR
9.4 16 reviews
Ashland, OR
18/09 – 20/09
NZ$356/nighttotal: NZ$712 (2 )

Chateau Herbe ~ Oberon Suite W/ Kitchen

1 2
apartment , Ashland
This Ashland apartment, a mile (1.6km) from Ashland Dog Park and within three miles (4.8km) of Lithia Park, North Mountain Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre, offers stunning mountainside views.
The one-bedroom, one-bathroom flat sleeps four, boasting a fully equipped kitchen, private balcony, shared garden, Smart TV, and parking; nearby activities include exploring Ashland's renowned parks and theatres.
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, OR
9.4 3 reviews
Ashland, OR
07/10 – 12/10
NZ$2407/nighttotal: NZ$12035 (5 )

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 4
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.
Hot Tub | Sauna |Firepit |Sleeps 6! - Ashland, OR
10 5 reviews
Ashland, OR
18/09 – 20/09
NZ$1573/nighttotal: NZ$3146 (2 )

Hot Tub | Sauna |Firepit |Sleeps 6!

2 2
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.

Best pet friendly Ashland, OR holiday rentals

Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals

Swank Suites | King With Lux Tub - Ashland, OR
Ashland, OR
19/07 – 14/08
NZ$432/nighttotal: NZ$11232 (26 )

Swank Suites | King With Lux Tub

1 1
apartment , Ashland
This Ashland city centre apartment is ideally located within a short walk of the Oregon Shakespeare Festival and Lithia Park, and a block from a grocery store.
The 28-square-metre studio flat offers a king-size bed, two bathrooms, a kitchenette with microwave and mini-refrigerator, and access to a private outdoor lounge; it sleeps two guests and boasts high-speed 5G internet.
The Matriarch| Suite 3 | Pet Friendly - Ashland, OR
9.9 172 reviews
Ashland, OR
04/08 – 06/08
NZ$413/nighttotal: NZ$826 (2 )

The Matriarch| Suite 3 | Pet Friendly

1 2
apartment , Ashland
This Ashland apartment, a private suite within a historic 1894 house, enjoys a central location, offering immediate proximity to Ashland's award-winning restaurants, theatres, and shops.
The self-contained unit features a king-size bed, separate living area with streaming services (Netflix, Disney+, Hulu), a French bistro kitchenette, and accommodates two guests; shared summer patio seating and a communal BBQ are also available.
One Bedroom One Bathroom Studio With Full Kitchen And Stunning Patio. - Ashland, OR
10 2 reviews
Ashland, OR
07/10 – 12/10
NZ$560/nighttotal: NZ$2800 (5 )

One Bedroom One Bathroom Studio With Full Kitchen And Stunning Patio.

1 4
studio , Ashland
This Ashland cottage, situated in the Historic Railroad District, is within a 1.7km walk of Lithia Park and less than 1km from the Oregon Cabaret Theatre.
The one-bedroom, one-bathroom self-catering property sleeps two guests and offers Wi-Fi, air conditioning, and essential toiletries; nearby attractions include the Ashland Creek and US Cellular Community Park.
Thistle Bee House - Ashland, OR
9.8 20 reviews
Ashland, OR
25/08 – 26/08
NZ$874/nightfor 1 night

Thistle Bee House

1 3
apartment , Ashland
This Ashland countryside cottage, located 5-8 minutes (approximately 3-5km) from Ashland's downtown area and the Oregon Shakespeare Festival, offers easy access to local wineries.
Sleeping eight guests, this four-bedroom, two-bathroom property boasts a large fenced backyard with a dog kennel, a grape arbor seating area, and a fully equipped kitchen including a dishwasher, plus air conditioning and Wi-Fi.
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