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Ashland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Ashland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Enjoy the perfect mix of walkable Ashland and your private, airy, urban hideaway. Set in the historic Railroad District with fabulous cafes, restaurants and shops in the same block and nearby, this modern studio over a detached garage has views of trees or mountains from every window. It's only a 5 minute walk to Downtown and a 10 minute walk to Lithia Park and the Oregon Shakespeare Festival. Should you wish, you could park your car in your dedicated space and not use it again during your stay.
$135 per night
Superhost
Guesthouse in Ashland
Charming cottage, walk to town.
Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown
$150 per night
Superhost
Guesthouse in Ashland
Charming Guest House - One block from Downtown!
This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.
$125 per night

Stay near Ashland's top sights

Lithia Park198 locals recommend
Oregon Shakespeare Festival267 locals recommend
Ashland's Own Shop'n Kart38 locals recommend
Brickroom76 locals recommend
Ashland Food Co-op91 locals recommend
Ashland Springs Hotel3 locals recommend

Ashland house rentals

Superhost
Home in Ashland
Coyote Moon
$180 per night
Superhost
Home in Ashland
Ashland Haus Retreat - 1 block from downtown!
$190 per night
Superhost
Home in Ashland
Beautiful and peaceful cottage close to downtown
$195 per night
Superhost
Home in Ashland
Secluded Forest Log House 15 minutes to Ashland
$182 per night
Superhost
Home in Ashland
Terra Cottage Inn - Quintesential Ashland
$185 per night
Superhost
Home in Ashland
Premier Downstairs Flat in great Downtown Location
$269 per night
Superhost
Home in Ashland
ABBOTT'S COTTAGES - Falcon
$200 per night
Superhost
Home in Jacksonville
Unwind at a Luxury Cottage in Jacksonville's Historic Core
$190 per night
Superhost
Home in Jacksonville
Britt Bungalow in the Heart of Jacksonville
$268 per night
Superhost
Home in Medford
Cheerful new 2 bedroom home in cul de sac Netflix
$89 per night
Superhost
Home in Ashland
Spacious Historic Downtown Home!
$60 per night
Superhost
Home in Ashland
Farmhouse near emigrant lake and barrel sauna
$76 per night

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 110 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there Ashland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Ashland, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Ashland?

    Ashland has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in boutique hotel rentals in Ashland?

    Experience the best of Ashland with our boutique hotel rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do boutique hotel rentals in Ashland have wifi?

    Absolutely! We offer over 20 boutique hotel rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Ashland have self check-in?

    Absolutely! We offer over 10 apartment rentals with self check-in in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Ashland have a bbq area?

    Absolutely! We offer over 10 cottage rentals with a bbq area in Ashland. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland