Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

Our top choices for Ashland holiday homes

Chateau Herb ~ Miranda Carriage House Apt

9.6 out of 10, Exceptional, (4)
"Nice place to stay, with full kitchen, and a close drive to downtown Ashland. The AC stopped and the staff were very responsive and provided."
The price is AU$439
includes taxes & fees
1 Sept - 2 Sept
Chateau Herb ~ Miranda Carriage House Apt

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

9.6 out of 10, Exceptional, (79)
"The cottage was clean, comfortable, and very well situated in town. The kitchen was well equipped, allowing us to cook most of our meals there. It's in a quiet neighborhood where you can walk to anything you might want."
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

A beautiful Skyfall Landing

10.0 out of 10, Exceptional, (9)
"We like it because it was nice and quite staying out of the city it was great "
The price is AU$620
includes taxes & fees
25 Sept - 26 Sept
A beautiful Skyfall Landing

Downtown Ashland House - Walk to Plaza and OSF!

9.8 out of 10, Exceptional, (42)
"Perfect location; cute house - enjoyed our stay very much !"
Downtown Ashland House - Walk to Plaza and OSF!

Pet & family friendly 3bd house, central location, fenced yard.

9.8 out of 10, Exceptional, (7)
"Great place, plenty of space for family and fur babies. Centralized location. Would definitely stay here again "
Pet & family friendly 3bd house, central location, fenced yard.

3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.

9.6 out of 10, Exceptional, (44)
"A great place for a family getaway. Lots of room, loved all king beds, truly enjoyed the home."
3 bedrooms with king beds, 2 1/2 bathrooms. 2146 sq ft house in east Medford.

Entertainment Home on Golf Course - Hot Tub /Pool

10.0 out of 10, Exceptional, (8)
"We had an amazing time. The property is beautiful and the hosts are very responsive and easy to work with. The house is so amazing, you won’t want to leave."
Entertainment Home on Golf Course - Hot Tub /Pool

1907 Charmer, Perfect Downtown Location, So Clean!

9.4 out of 10, Exceptional, (120)
"Lovely little house, VERY conveniently located in Ashland. Beds are comfy and the communication was great. It is a very old house, so expect original wood floors. steep stairs, and small but very functional bathrooms. We'd stay there again! Great for our family -"
1907 Charmer, Perfect Downtown Location, So Clean!

Centrally located Historic Home with parking

8.6 out of 10, Excellent, (7)
"Loved the proximity to the Shakespeare Festival, downtown restaurants . Lithia Park and shopping: the grocery store was super close. We literally could walk everywhere! Host was great also. "
Centrally located Historic Home with parking

Comfy Cozy Casa

10.0 out of 10, Exceptional, (52)
"We had a great experience at this property and it was close in proximity to an event that we attended."
The price is AU$587
includes taxes & fees
15 Sept - 16 Sept
Comfy Cozy Casa

The Red Dragon House

10.0 out of 10, Exceptional, (92)
"We were looking for a nice quiet location close to the highway and this was perfect. It was very clean, the kitchen was beautiful and the welcome cookies were delicious. Thank you!"
The price is AU$310
includes taxes & fees
1 Sept - 2 Sept
The Red Dragon House

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

10.0 out of 10, Exceptional, (49)
"Perfect style for our family. Ages 3-75 stayed and each person enjoyed themselves! Well equipped for children."
The price is AU$898
includes taxes & fees
29 Sept - 30 Sept
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.

10.0 out of 10, Exceptional, (1)
The price is AU$441
includes taxes & fees
11 Sept - 12 Sept
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (143)
"A very comfortable space with easy access to theaters and restaurants."
Railroad District, steps to downtown, everything you need to enjoy Ashland!

In the historic railroad district, walking distance to all the best of Ashland!

10.0 out of 10, Exceptional, (189)
"We thoroughly enjoyed our stay in the house with easy access to everything in the theater district! The house is comfortable and well stocked. We'll be back!"
In the historic railroad district, walking distance to all the best of Ashland!

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

9.6 out of 10, Exceptional, (70)
"Great house within walking distance of downtown shops and restaurants "
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

Jacksonville Place

9.0 out of 10, Wonderful, (23)
"We enjoyed our stay here. When we first arrived, the cleaning staff was on their way. We left for dinner and came back to a clean house. We had what we needed for the 3 nights we were in town and plenty of room for me, my husband, three daughters and my mom. Fair price and decent place to stay. I’m sure we would stay here again if we come back through this area. "
The price is AU$376
includes taxes & fees
2 Sept - 3 Sept
Jacksonville Place

Red Barn in Wine Country

10.0 out of 10, Exceptional, (5)
"We loved the chickens and the animals and fresh garden. Road is a little loud at night but they do provide earplugs and it didn’t bother us too much but something to keep in mind if you are very sensitive to noise/light sleeper. Great stay overall! "
The price is AU$437
includes taxes & fees
1 Sept - 2 Sept
Red Barn in Wine Country

Cabin #4 at Hyatt Lake Resort

10.0 out of 10, Exceptional, (1)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
The price is AU$429
includes taxes & fees
10 Sept - 11 Sept
Cabin #4 at Hyatt Lake Resort

NEW Downtown Talent Dream

10.0 out of 10, Exceptional, (9)
"We really enjoyed our time at this property and will absolutely be back. The house was immaculate, had everything we needed and then some... a perfect rental house! Thank you! "
NEW Downtown Talent Dream
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Find out more about Ashland

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
3
Accommodation
303 Holiday Homes
Lowest Price
AU$310
Highest Price
AU$898