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The best vacation homes in Ashland

Check out our selection of great vacation homes in Ashland

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Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland, hotel in Ashland

Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland is located in Ashland, just a 15-minute walk from Lithia Park and 1.3 miles from Southern Oregon University.

Internet never worked
Scored 9.8
9.8
Rated exceptional
Exceptional
6 reviews
Price from
$242
1 night, 2 adults
Bluemoon Vacation Rentals - Bluemoon Cottage, hotel in Ashland

Bluemoon Vacation Rentals - Bluemoon Cottage is located in Ashland, just 1.1 miles from Lithia Park and 1.9 miles from ScienceWorks Museum.

Wonderful location Very quiet Clean Very nicely appointed Easy and secure access Free parking Full kitchen with utensils In walking distance to the food coop and the Shakespeare festival.
Scored 9.2
9.2
Rated wonderful
Wonderful
6 reviews
Price from
$153.90
1 night, 2 adults
Redtail Inn - 3 Suites Sleeps Up To 12, hotel in Ashland

A few steps from Ashland Library in Ashland, Redtail Inn - 3 Suites Sleeps Up To 12 provides accommodations with access to a hot tub.

Great location, lovely suite, nicely decorated. Very clean. The pour over coffee maker was missing a filter, but luckily one was delivered that afternoon, so I had coffee the next morning. Staff are responsive and helpful.
Scored 9.5
9.5
Rated exceptional
Exceptional
6 reviews
Price from
$138
1 night, 2 adults
The Mountain House by WanderLodges, hotel in Ashland

The Mountain House by WanderLodges offers accommodations in Ashland, a 16-minute walk from Oregon Cabaret Theatre and one mile from Oregon Shakespeare Festival.

Everything about renting the Mountains Avenue house was amazing- the location was great, the house itself is just gorgeous, everything was clean and neat and it’s so comfortably designed. The rooms are huge! And it’s dog friendly, which is wonderful. Thank you!
Scored 9.5
9.5
Rated exceptional
Exceptional
22 reviews
Price from
$247.20
1 night, 2 adults
1930s Queen Anne Historic Downtown Retreat, hotel in Medford

1930s Queen Anne Historic Downtown Retreat is located in Medford, just 12 miles from Oregon Shakespeare Festival and 13 miles from Oregon Cabaret Theatre.

The privacy of having 4 rooms.
Scored 9.1
9.1
Rated wonderful
Wonderful
19 reviews
Price from
$178.25
1 night, 2 adults
Southern Oregon Gem, hotel in Medford

Southern Oregon Gem offers accommodations in Medford, 13 miles from Oregon Shakespeare Festival and 13 miles from Oregon Cabaret Theatre.

Very cozy and comfortable house that is simply and tastefully decorated. The owner is very accommodating and replies promptly.
Scored 8.9
8.9
Rated excellent
Excellent
9 reviews
Price from
$79.38
1 night, 2 adults
Oakdale Suites - Master Property, hotel in Medford

Oakdale Suites - Master Property offers accommodations in Medford, 13 miles from Oregon Shakespeare Festival and 13 miles from Oregon Cabaret Theatre.

Clean, well laid out, nice decor, bed was comfortable, close to stores
Scored 8.7
8.7
Rated excellent
Excellent
81 reviews
Price from
$77
1 night, 2 adults
Fantastic Bright 4 Bedroom- Deck - Fireplaces, hotel in Medford

Featuring a seasonal outdoor swimming pool, Fantastic Bright 4 Bedroom- Deck - Fireplaces offers accommodations in Medford. This property offers access to a terrace and free private parking.

I enjoyed the patio, everything but the patio the most
Scored 8.9
8.9
Rated excellent
Excellent
7 reviews
Price from
$218.50
1 night, 2 adults
Comfortable Jacksonville house, hotel in Medford

Comfortable Jacksonville house is located in Medford, just 14 miles from Oregon Cabaret Theatre and 14 miles from Ashland Library.

This place is really nice and very well kept. We really liked the house. Bedrooms were good size. Bathrooms were very nice. Hardwood floors throughout was a nice touch. Also the owners responed quickly when messaged also. Would love to stay again.
Scored 8.2
8.2
Rated very good
Very Good
21 reviews
Price from
$151.47
1 night, 2 adults
Hot Tub! King Bed-firepitt-near Airport& Freeway, hotel in Medford

Hot Tub! King Bed-firepitt-near Airport& Freeway is located in Medford, just 16 miles from Oregon Cabaret Theatre and 16 miles from Ashland Library.

The hot tub close to everything and beautiful home
Scored 9.1
9.1
Rated wonderful
Wonderful
27 reviews
Price from
$161
1 night, 2 adults
All vacation homes in Ashland
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Ashland this month

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Enjoy breakfast in Ashland!

  • Expansive Views at The Crest House by Swank House
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 8 reviews

    Expansive Views at The Crest House by Swank House offers accommodations in Ashland, 1.9 miles from Schneider Museum of Art and 2.1 miles from Southern Oregon University.

    It really was a fabulous place. The views are incredible. Perfect for our family of five. Comfortable beds. Great shower. Very stylish.

  • Second Street Cottages
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 29 reviews

    Second Street Cottages provides rooms in Ashland near Southern Oregon University and Lithia Park. This property offers access to a patio, free private parking, and free Wifi.

    Location is great and the cottage is nicely furnished

  • European Style Straw Bale Retreat
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 6 reviews

    European Style Straw Bale Retreat is located in Ashland, just 2.9 miles from Schneider Museum of Art and 3.2 miles from Southern Oregon University.

  • Grandview of Ashland

    Providing a garden, Grandview of Ashland offers accommodations in Ashland. This property offers access to a terrace and free private parking.

  • Historic Dunn Ranch Ashland Oregon

    Historic Dunn Ranch Ashland Oregon is located in Ashland, just 1.3 miles from Oak Knoll Golf Course and 3.4 miles from Schneider Museum of Art.

  • Serene Family Cottage-minutes to Downtown
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Serene Family Cottage-minutes to Downtown offers accommodations in Ashland, 1.1 miles from Oak Knoll Golf Course and 2.5 miles from Schneider Museum of Art.

  • Pioneer Vacation Rentals - Pioneer Craftsman House

    Pioneer Vacation Rentals - Pioneer Craftsman House offers accommodations in Ashland, a 15-minute walk from Lithia Park and 1.3 miles from Southern Oregon University.

  • Hanna's House by WanderLodges
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 2 reviews

    Just a 5-minute walk from Oregon Cabaret Theatre and 700 yards from Oregon Shakespeare Festival, Hanna's House by WanderLodges features accommodations in Ashland, with a garden and a terrace.

Great access to the city center! Check these vacation homes in Ashland

  • Pioneer Vacation Rentals - Pioneer South downtown Ashland
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 reviews

    Pioneer Vacation Rentals - Pioneer South downtown Ashland offers accommodations in Ashland, 1.3 miles from Southern Oregon University and 1.6 miles from Schneider Museum of Art.

  • Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 6 reviews

    Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland is located in Ashland, just a 15-minute walk from Lithia Park and 1.3 miles from Southern Oregon University.

  • Redtail Inn - 3 Suites Sleeps Up To 12
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 6 reviews

    A few steps from Ashland Library in Ashland, Redtail Inn - 3 Suites Sleeps Up To 12 provides accommodations with access to a hot tub.

    Beautiful house, great location and very responsive host! Loved the kitchen, shower and bedroom.

  • The Mountain House by WanderLodges
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 22 reviews

    The Mountain House by WanderLodges offers accommodations in Ashland, a 16-minute walk from Oregon Cabaret Theatre and one mile from Oregon Shakespeare Festival.

    Very spacious & nicely refurbished classic home.

  • Bluemoon Vacation Rentals - Bluemoon Cottage
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 6 reviews

    Bluemoon Vacation Rentals - Bluemoon Cottage is located in Ashland, just 1.1 miles from Lithia Park and 1.9 miles from ScienceWorks Museum.

    The property was centered in Ashland and I could easily access everything.

  • The Matriarch Heritage House- Downtown Ashland
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    Just a 5-minute walk from Oregon Shakespeare Festival and 300 yards from Oregon Cabaret Theatre, The Matriarch Heritage House- Downtown Ashland features accommodations in Ashland with a garden.

  • Ashland Cabin on 170 Acres with Mtn Views and Sauna!
    Scored 6.0
    6.0
    Rated pleasant
    Pleasant
     · 2 reviews

    17 miles from Schneider Museum of Art in Ashland, Ashland Cabin on 170 Acres with Mtn Views and Sauna! offers accommodations with access to a fitness room.

  • Bluemoon Vacation Rentals - Bluemoon House

    Bluemoon Vacation Rentals - Bluemoon House is located in Ashland, just 1.9 miles from ScienceWorks Museum and 1.9 miles from Southern Oregon University.

  • Bluemoon Vacation Rentals - Anne Hathaway House

    Bluemoon Vacation Rentals - Anne Hathaway House offers accommodations in Ashland, a 17-minute walk from Southern Oregon University and 1.1 miles from ScienceWorks Museum.

  • Hyatt Lake Resort
    Central location

    Hyatt Lake Resort enjoys a location in Ashland, 21 miles from Oak Knoll Golf Course and 23 miles from Schneider Museum of Art.

  • Ashland Lodge with Lake Views and Game Room Loft

    Ashland Lodge with Lake Views and Game Room Loft is located in Ashland, just 28 miles from Schneider Museum of Art and 28 miles from ScienceWorks Museum.

FAQ about vacation homes in Ashland

Vacation Homes That Guests Love in Ashland

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  • Avg. price/night: $83.63
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 140 reviews
    Very clean. Comfortable bed, loved the granite shower. Excellent value, the stay exceeded all expectations. Only 1 of 2 hotels during 2 weeks of travel that even MET expectations and this one excelled.
    shelly
    Young couple
  • Avg. price/night: $133.80
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 1,465 reviews
    Rooms very clean, friendly staff, large bathroom
    Kate
    Family with young children
  • Avg. price/night: $206.36
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 390 reviews
    Great location. Very clean and comfortable faculty with helpful staff. The on-site at and restaurant are excellent!
    Kevin
    Young couple
  • Avg. price/night: $133.80
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 1,465 reviews
    Very tasteful decor with posters from past Shakespeare festivals. The rooms have hardwood floors and are kept very clean, there is a fridge and microwave in the room. Staff are very friendly too. The location next door to Safeway is a bonus.
    Sean
    Young couple
  • Avg. price/night: $69.13
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 1,279 reviews
    Front desk people were very nice and welcoming. Check in super easy. Had a first floor room as requested. Outside the motel is very clean and well cared for. Room was spacious. Very comfortable bed, great shower, separate sink area. Quiet in the night. Easy access to Southern Oregon University and downtown area.
    Julie
    Young couple
  • Avg. price/night: $122.65
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 823 reviews
    We had a two room suite. It was small, but very clean and comfortable. The beds were great.
    Laurie
    Group
  • Avg. price/night: $69.13
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 1,279 reviews
    Great location Friendly helpful staff Very clean Kitchenette Continental breakfast
    Maggie
    Young couple
  • Avg. price/night: $133.80
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 1,465 reviews
    Best hotel I have stayed in.very clean friendly great breakfast very cozy seating outside pet friendly I have already planning a trip back and have recommended it to family and friends awesome stay
    K
    KIMBERLY
    Solo traveler
  • Avg. price/night: $133.80
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 1,465 reviews
    The staff, the location, the room was very clean and cosy.
    anna
    Young couple
  • Avg. price/night: $117.08
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 540 reviews
    Room was large and very clean. Bed was comfortable.
    Eileen
    Young couple