Ashland vacation rentals

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Top-rated vacation rentals in Ashland

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

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 427 reviews

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

Nov 19 – 26

R3,230 ZAR per night
Guest favorite

Cottage in Phoenix

4.91 out of 5 average rating, 310 reviews

The Pear Cottage Where city and country life meet

This is on a 42 acre family farm that dates back to 1910. Beautiful, quiet and very relaxing. We think you will love this completely renovated living space. With a private deck off each bedroom with lots of outdoor seating. Our home is just minutes away from Ashland Shakespeare and Jacksonville Britt Festivals. We are surrounded by the most breathtaking wineries, Skiing, Hiking the Pacific Crest Trail, Crater Lake and lots more. Enjoy looking out of the beautiful hay field and having coffee.

Apr 8 – 15

R1,992 ZAR per night
Guest favorite

Tiny home in Shady Cove

4.95 out of 5 average rating, 194 reviews

Modern Tiny House w/ Hot Tub

Located on a hillside in Shady Cove. This is a spacious brand new 300 sq foot tiny home. The tiny house is located on our private property. We request for our guests to be respectful of our home, our neighbors, and surroundings. It is important that our guests treat the outdoor space as if they were camping and not leave any food outside as there is some wildlife in the area. Included is a covered gazebo with curtains on a private deck with a spa, and gas fire pit that also heats your legs.

Aug 29 – Sep 5

R2,613 ZAR per night

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

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

Ashland house rentals

Guest favorite

Home in Ashland

4.95 out of 5 average rating, 178 reviews

Coyote Moon

Jan 14 – 21

R4,370 ZAR per night
Guest favorite

Home in Ashland

4.96 out of 5 average rating, 238 reviews

Secluded Forest Log House 15 minutes to Ashland

Nov 29 – Dec 6

R3,379 ZAR per night
Guest favorite

Home in Ashland

4.95 out of 5 average rating, 105 reviews

Casa Bella

Mar 1 – 8

R6,883 ZAR per night
Guest favorite

Home in Grants Pass

4.98 out of 5 average rating, 333 reviews

Charming Cottage, Walk To Historic Downtown!

Apr 4 – 11

R1,899 ZAR per night
Guest favorite

Home in Ashland

4.91 out of 5 average rating, 190 reviews

Ashland Haus Retreat - 1 block from downtown!

Feb 22 – Mar 1

R3,963 ZAR per night
Guest favorite

Home in Ashland

4.96 out of 5 average rating, 129 reviews

High Street Cottage, Artist's Garden Cottage

Nov 26 – Dec 3

R3,615 ZAR per night
Guest favorite

Home in Grants Pass

4.81 out of 5 average rating, 326 reviews

Modern Studio in the Heart of Grants Pass

Sep 15 – 22

R1,279 ZAR per night
Guest favorite

Home in Grants Pass

4.97 out of 5 average rating, 285 reviews

Gateway to Cathedral hills

Sep 11 – 18

R3,106 ZAR per night
Guest favorite

Home in Grants Pass

4.92 out of 5 average rating, 167 reviews

Cedar Mountain Suite A -Home Theater, Gamer Ready!

Feb 12 – 19

R1,979 ZAR per night
Guest favorite

Home in Jacksonville

4.99 out of 5 average rating, 248 reviews

Britt Bungalow in the Heart of Jacksonville

Jan 22 – 29

R5,298 ZAR per night
Guest favorite

Home in Trail

4.95 out of 5 average rating, 210 reviews

Log Cabin w/Treehouse & Zip Line on Rogue River

May 24 – 31

R8,790 ZAR per night
Guest favorite

Home in Gold Hill

4.99 out of 5 average rating, 209 reviews

Rogue River Retreat

Jan 8 – 15

R4,272 ZAR per night

Other great vacation rentals in Ashland

Guest favorite

Camper/RV in Ashland

4.88 out of 5 average rating, 913 reviews

Cozy camping close to town

Apr 28 – May 5

R1,029 ZAR per night
Guest favorite

Farm stay in Ashland

5.0 out of 5 average rating, 116 reviews

Kelly’s Carriage House 4 miles from Ashland

Jun 7 – 14

R2,835 ZAR per night
Guest favorite

Farm stay in Ashland

4.94 out of 5 average rating, 589 reviews

Kelly’s Farm 4 miles to Ashland

Aug 13 – 20

R3,175 ZAR per night
Guest favorite

Cabin in Ashland

4.96 out of 5 average rating, 155 reviews

Beautiful Barndominium by Howard Prairie Lake

Dec 8 – 15

R3,408 ZAR per night
Guest favorite

Tiny home in Grants Pass

4.97 out of 5 average rating, 141 reviews

Tiny Cottage w/Firepit/Hottub/Outdoor tubs

Jan 5 – 12

R2,322 ZAR per night
Guest favorite

Cottage in Ashland

4.97 out of 5 average rating, 421 reviews

Victorian Garden Carriage House

Mar 19 – 26

R3,721 ZAR per night
Guest favorite

Cottage in Ashland

4.99 out of 5 average rating, 140 reviews

The Red Dragon House

Jan 9 – 16

R3,657 ZAR per night
Guest favorite

Guesthouse in Ashland

4.94 out of 5 average rating, 109 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

Feb 13 – 20

R2,730 ZAR per night
Guest favorite

Cabin in Grants Pass

4.98 out of 5 average rating, 409 reviews

The Cozy Cabin (with own private hot tub!)

Jul 27 – Aug 3

R2,636 ZAR per night
Guest favorite

Treehouse in Jacksonville

4.98 out of 5 average rating, 183 reviews

Tree Top Studio

Aug 16 – 23

R3,992 ZAR per night
Guest favorite

Guesthouse in Medford

4.94 out of 5 average rating, 152 reviews

Modern, pet-friendly, private - EV charger level 2

Feb 17 – 24

R1,908 ZAR per night
Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 698 reviews

BEE WELL Organic Spa Garden Studio

Aug 7 – 14

R1,607 ZAR per night

Quick stats about vacation rentals in Ashland

Total rentals

280 properties

Rentals with dedicated workspaces

140 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

19K reviews

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 140 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 100 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 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in bed and breakfast rentals in Ashland?

    Experience the best of Ashland with our bed and breakfast rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do guesthouse rentals in Ashland have wifi?

    Absolutely! We offer over 30 guesthouse rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ashland have a gym?

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

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

    Absolutely! We offer over 30 house 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.

  • What are the most popular amenities for House Rentals in Ashland?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 90 homes with wifi, over 10 homes with a gym, over 30 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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