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The best holiday homes in Ashland

Check out our pick of great holiday homes in Ashland

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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The spacious holiday home has 3 bedrooms, 1 bathroom, bed linen, towels, a flat-screen TV, a dining area, a fully equipped kitchen, and a terrace with mountain views. This holiday home also comes with a patio that doubles up as an outdoor dining area. Additional in-room amenities include chocolates or cookies.

The views at this house are worth EVERY PENNY! Having a morning coffee overlooking and magnificent view made me feel like I was experiencing true zen.

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9.8
Exceptional
6 reviews
Price from
£422
per night

The spacious holiday home features 3 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a shower. Towels and bed linen are featured in the holiday home. At the holiday home, there is a dressing room for guests to change in.

Such a neat house remodel! Felt very safe and had everything ewe needed.

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9.6
Exceptional
8 reviews
Price from
£367
per night

Second Street Cottages is a historic home offering accommodation in Ashland. Free WiFi is offered throughout the property and free private parking is available on site.

Second Street Cottages is within walking distance to the biggest event in Ashland, The Shakespeare Festival Theater. The nearest airport is Rogue Valley Airport, 24 km from Second Street Cottages. Unique shops, restaurants, wineries are nearby.

The host met us and helped us with the door code. This place was in a great location near by everything we were hoping to see on our visit. It was a cozy tidy place to stay.

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9.6
Exceptional
29 reviews
Price from
£209
per night

This villa comes with 2 bedrooms, a kitchen with a dishwasher and an oven, a flat-screen TV, a seating area and 1 bathroom equipped with a bath. The parquet floors, fireplace and peaceful vibe add to the ambience of the room. The property has an outdoor dining area.

It was 100 degrees+ outside when we were there, and the house stayed nice and cool inside. The house was well-appointed, nicely designed, and well-stocked with everything we needed (cookware, towels, etc). Lots of areas to chill and spread out. Comfy beds. Huge soaking tub in the bathroom! Very short drive to town. Hosts were great ... and responsive. Learning about the house and property was fun.

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8.2
Very good
5 reviews
Price from
£292
per night

The spacious holiday home features 3 bedrooms, a flat-screen TV and a fully equipped kitchenette that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are available in the holiday home. For added privacy, the accommodation features a private entrance.

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10
Exceptional
2 reviews
Price from
£483
per night

The holiday home with a balcony and city views has 2 bedrooms, a living room, a flat-screen TV, an equipped kitchenette with a dishwasher and a microwave, and 1 bathroom with a walk-in shower. A private entrance leads guests into the holiday home, where they can enjoy some wine or champagne and chocolates or cookies.

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10
Exceptional
2 reviews
Price from
£423
per night

Ashland Library is 1.3 km from the holiday home, while Lithia Park is 1.8 km from the property. The nearest airport is Rogue Valley International-Medford Airport, 37 km from Bluemoon Vacation Rentals - Bluemoon Cottage.

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9
Superb
2 reviews
Price from
£254
per night

Redtail Inn - 3 Suites Sleeps Up To 12, a property with a terrace, is located in Ashland, 100 metres from Ashland Library, 500 metres from Oregon Cabaret Theatre, as well as 700 metres from Oregon Shakespeare Festival. This holiday home is 1.7 km from Lithia Park and 5.4 km from Oak Knoll Golf Course. The holiday home provides rooms with air conditioning, free private parking and free WiFi.

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9
Superb
2 reviews
Price from
£207
per night

The holiday home is composed of 2 bedrooms, a fully equipped kitchen, and 2 bathrooms. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance.

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10
Exceptional
3 reviews
Price from
£520
per night

Situated in Ashland, 700 metres from Southern Oregon University and less than 1 km from Schneider Museum of Art, Hot Tub & Seasonal Pool -Sleeps 10- 4 min to OSF offers air conditioning. This holiday home has a private pool, a garden and free private parking. The property is non-smoking and is set 1.3 km from Ashland Library.

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10
Exceptional
1 reviews
Price from
£368
per night

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Ashland this month

Enjoy breakfast in Ashland!

  • The Mountain House by WanderLodges
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews

    The Mountain House by WanderLodges is situated in Ashland, 1 km from Ashland Library, 1.4 km from Oregon Cabaret Theatre, as well as 1.6 km from Oregon Shakespeare Festival.

    Such a neat house remodel! Felt very safe and had everything ewe needed.

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

    Second Street Cottages is a historic home offering accommodation in Ashland. Free WiFi is offered throughout the property and free private parking is available on site.

    Location is great and the cottage is nicely furnished

  • European Style Straw Bale Retreat
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 5 reviews

    Featuring mountain views, European Style Straw Bale Retreat provides accommodation with a garden and a patio, around 4.7 km from Schneider Museum of Art.

  • Serene Family Cottage-minutes to Downtown

    Boasting air-conditioned accommodation with a patio, Serene Family Cottage-minutes to Downtown is situated in Ashland.

  • Make memories at The Hux- Ashland

    Boasting air-conditioned accommodation with a patio, Make memories at The Hux- Ashland is set in Ashland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Situated 600 metres from Ashland Library, 1.3 km from Lithia Park and 2.1 km from Southern Oregon University, Pioneer Vacation Rentals - Pioneer North Suite downtown Ashland offers accommodation...

  • Bluemoon Vacation Rentals - Anne Hathaway House

    Set in Ashland, 300 metres from Ashland Library and 700 metres from Oregon Cabaret Theatre, Bluemoon Vacation Rentals - Anne Hathaway House offers spacious air-conditioned accommodation with a patio...

  • Savage Upon Siskiyou Spacious 3BDR near Railroad District

    Located in Ashland in the Oregon region, with Ashland Library and Oregon Cabaret Theatre nearby, Savage Upon Siskiyou Spacious 3BDR near Railroad District provides accommodation with free WiFi and...

Save money on holiday homes in Ashland – budget options available!

  • Swank House on Main St in Ashland
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Set in Ashland, 200 metres from Ashland Library and 600 metres from Oregon Cabaret Theatre, Swank House on Main St in Ashland offers air conditioning.

  • Hot Tub & Seasonal Pool -Sleeps 10- 4 min to OSF
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in Ashland, 700 metres from Southern Oregon University and less than 1 km from Schneider Museum of Art, Hot Tub & Seasonal Pool -Sleeps 10- 4 min to OSF offers air conditioning.

  • Ashland Lodge with Lake Views and Game Room Loft

    Situated in Ashland, 41 km from Oak Knoll Golf Course and 45 km from Schneider Museum of Art, Ashland Lodge with Lake Views and Game Room Loft features air-conditioned accommodation with a patio and...

  • Ashland Cabin on 170 Acres with Mtn Views and Sauna!
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Boasting garden views, Ashland Cabin on 170 Acres with Mtn Views and Sauna! features accommodation with a garden and a patio, around 23 km from Oak Knoll Golf Course.

Great access to the city centre! Check these holiday homes in Ashland

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

    Pioneer Vacation Rentals - Pioneer South downtown Ashland is located in Ashland, 600 metres from Ashland Library, 1.3 km from Lithia Park, and 2.1 km from Southern Oregon University.

  • Expansive Views at The Crest House by Swank House
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 reviews

    Expansive Views at The Crest House by Swank House is set in Ashland, 3.4 km from Southern Oregon University, 3.8 km from ScienceWorks Museum, as well as 4.7 km from Ashland Library.

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

  • Bluemoon Vacation Rentals - Bluemoon Cottage
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Offering quiet street views, Bluemoon Vacation Rentals - Bluemoon Cottage is an accommodation situated in Ashland, less than 1 km from Oregon Shakespeare Festival and a 12-minute walk from Oregon...

  • Redtail Inn - 3 Suites Sleeps Up To 12
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Redtail Inn - 3 Suites Sleeps Up To 12, a property with a terrace, is located in Ashland, 100 metres from Ashland Library, 500 metres from Oregon Cabaret Theatre, as well as 700 metres from Oregon...

  • Pioneer Vacation Rentals - Pioneer Craftsman House

    Boasting air-conditioned accommodation with a balcony, Pioneer Vacation Rentals - Pioneer Craftsman House is set in Ashland. With city views, this accommodation offers a patio.

  • The Matriarch Heritage House- Downtown Ashland

    Boasting air-conditioned accommodation with a patio, The Matriarch Heritage House- Downtown Ashland is situated in Ashland.

  • Hanna's House by WanderLodges

    Located in Ashland, 200 metres from Ashland Library and 500 metres from Oregon Cabaret Theatre, Hanna's House by WanderLodges offers a garden and air conditioning.

  • Bluemoon Vacation Rentals - Bluemoon House

    Set in Ashland, less than 1 km from Oregon Shakespeare Festival and a 12-minute walk from Oregon Cabaret Theatre, Bluemoon Vacation Rentals - Bluemoon House offers spacious air-conditioned...

FAQ about holiday homes in Ashland





Holiday homes that guests love in Ashland

  • Avg. price/night: £96.69
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 152 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
  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,489 reviews
    Rooms very clean, friendly staff, large bathroom
    Kate
    Family with young children
  • Avg. price/night: £294.29
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 351 reviews
    Great location. Very clean and comfortable faculty with helpful staff. The on-site at and restaurant are excellent!
    Kevin
    Young couple
  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,489 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: £104.60
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 1,419 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: £167.01
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 882 reviews
    We had a two room suite. It was small, but very clean and comfortable. The beds were great.
    Laurie
    Group
  • Avg. price/night: £104.60
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 1,419 reviews
    Great location Friendly helpful staff Very clean Kitchenette Continental breakfast
    Maggie
    Young couple
  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,489 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 traveller
  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,489 reviews
    The staff, the location, the room was very clean and cosy.
    anna
    Young couple
  • Avg. price/night: £140.64
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 515 reviews
    Room was large and very clean. Bed was comfortable.
    Eileen
    Young couple
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