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Guesthouse holiday rentals in Ashland

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Ashland guesthouses

Family-Friendly guesthouses

Guesthouse in Central Point
4.87 out of 5 average rating, 291 reviews

The Peaceful Log Room: 1 Bedroom Guesthouse

DanielleRating, 5 stars35 months ago
Great location, close to wineries and Jacksonville.
Top Guest favourite
Guesthouse in Gold Hill
4.74 out of 5 average rating, 63 reviews

Dream Cottage on the Rogue River

MauraRating, 5 stars1 month ago
This really is a dream cottage! It’s right on the Rogue River. My dog and I woke up every morning and went down to the river, and it was never the same twice. Incredible birding, and even saw some river otters! Sam’s sculpture adds a lot of fun surprises to the property- you never know what’s going to appear. The bed was very comfortable, and the kitchen has everything you need to feel right at home. Sam and Paula were so kind and welcoming. Can’t recommend it enough!
Superhost
Guesthouse in Medford
4.68 out of 5 average rating, 142 reviews

Million Dollar View No city tax! Huge 4k tvs

StevieRating, 5 stars3 days ago
This place was perfect for my bigger size family and our pet! Very comfortable and had beautiful views! We definitely recommend this home and would definitely go back!!
Guest favourite
Guesthouse in Gold Hill
4.97 out of 5 average rating, 88 reviews

Rogue River Guesthouse: Rural river views near I-5

VirginiaRating, 5 stars1 week ago
We had a wonderful stay at this Airbnb. It is a cozy and inviting space! The beds were comfortable, and everything was very clean. The hosts have considered nearly every detail you might need in the kitchen, bathroom, and bedrooms. They provide a link with useful information, which was helpful. We truly felt at home. The sound of the river at night was priceless. The place offered great privacy, allowing for a genuinely relaxing experience. Thank you for making everything a breeze.
Guest favourite
Guesthouse in Grants Pass
4.94 out of 5 average rating, 453 reviews

Sweet Vintage Cottage steps from Rogue River

JulianRating, 5 stars2 days ago
Very beautiful area. Had lots of fun in the awesome pool. My daughter was amazed at all the wildlife in the area. The room was very charming and had a rustic feel to it, but had all the modern amenities. All in all we had a great time and couldn't ask for a better location or host. Teresa was very friendly and helpful
Superhost
Guesthouse in Ashland
4.86 out of 5 average rating, 145 reviews

ABBOTT'S COTTAGES- Egret

HossainRating, 5 stars1 month ago
Had an excellent stay here. Would absolutely stay again. Space was just right. Excellent hosts!
Guesthouse in Medford
4.96 out of 5 average rating, 70 reviews

Roxy Ann Retreat - Large Luxury Carriage House

HalseyRating, 5 stars2 months ago
This home was in a quiet, stunning neighborhood with a gorgeous view. We got to watch the sunset from bed! All of the furniture was comfy, cozy, clean, and smelled good. Elyse was so responsive and helped us with a question/request right away. The home was in the perfect center of all of the things we wanted to do while we visited, and so close to a cafe/wine tasting room/food truck spot. We were so happy we chose this place for our long weekend get away.
Top Guest favourite
Guesthouse in Medford
4.95 out of 5 average rating, 183 reviews

Comice Valley Apartment with EV Charger

SalmaRating, 5 stars3 weeks ago
Had a great stay here! Jim was a very welcoming host who accommodated a last minute stay. The place was very comfortable, and Jim gave very clear instructions that I appreciated

Guesthouses with a patio

Top Guest favourite
Guesthouse in Talent
5 out of 5 average rating, 11 reviews

1910 Orchard Guest House

RachelRating, 5 stars4 days ago
We would definitely stay at this Airbnb again! The property is so quaint and peaceful. The location is very close to Ashland and is a must stay.
Top Guest favourite
Guesthouse in Grants Pass
4.98 out of 5 average rating, 120 reviews

Serene Upstairs Studio with Bath & Kitchenette

LheaRating, 5 stars2 weeks ago
Staying at Ivan's this past week was exactly what my little family and I needed! We live in Grants Pass but, we love to do little getaways/staycation. His studio and propert were beautiful, quiet and, peaceful. Loved watching the chickens and babies. Definitely recommend for a staycation or if you're from out of town this is an amazing little Airbnb.
Top Guest favourite
Guesthouse in Medford
5 out of 5 average rating, 40 reviews

The Peach Pit Inn! A sunny retreat w self check-in

CaseyRating, 5 stars3 weeks ago
we had a great stay at peach pit in it was so cute and you can tell Rebecca really paid attention to the details. definitely better than staying in a hotel!
Guest favourite
Guesthouse in Ashland
5 out of 5 average rating, 12 reviews

Hanna's House by WanderLodges |1 block to downtown

IreneRating, 5 stars2 weeks ago
As advertised! Hanna’s house was in a terrific location (VERY walkable to all the things, but tucked away enough that I heard no noise at night), and every thoughtful detail accompanied this Airbnb. Loved it.
Guest favourite
Guesthouse in Jacksonville
4.96 out of 5 average rating, 112 reviews

La Petite Maison + Spa

MichaelRating, 5 stars2 weeks ago
The cottage and the property are idyllic and the owners (Nicole and Fernando) are wonderful. They are friendly, accessible, responsive and just about everything you'd want or expect from the host. All of the amenities were as shown and advertised. The only "negatives" were (1) the fact that this a country property means lots of flying and crawling insects, and (2) the property is in a remote country setting. If you're looking for a quiet, relaxing place to unwind, this spot is a gem. If you're interested in a convenient place to stay while enjoying social experiences (dining, theater, shopping, etc.), be prepared to drive a bit.
Superhost
Guesthouse in Ashland
4.5 out of 5 average rating, 4 reviews

Sunset Cottage at Grizzly Peak Winery

SanheshkeRating, 5 stars6 months ago
I cannot say enough wonderful things about this place. It’s enchantingly serene, the property is immense with walking trails everywhere, the on-site hosts, Virginia and Al, are incredibly welcoming and exceedingly kind. They are some of the sweetest people I have ever met. We were greeted by them on arrival with some wine and chocolate for the holiday. We enjoyed the stars every night we were there and the space itself is absolutely beautiful. It is the definition of “home away from home” and I hope I get to visit again someday!
Top Guest favourite
Guesthouse in Ashland
4.95 out of 5 average rating, 37 reviews

Silver Frog Guesthouse- downtown Ashland 'hood

EllenRating, 5 stars1 week ago
Susan is an experienced, friendly, and thoughtful host. The Silver Frog studio is well-designed for a couple and has a lovely outdoor shaded patio and garden area for relaxing with morning coffee provided in unit. Location is easily walkable to OSF theaters, Lithia Park, restaurants, everything downtown and the historic Railroad District! No need to have a car, but if you do, off-street parking is provided on-site. Silver Frog Studio is a rare find, a sweet spot for a getaway, with so much to do close-by!
Guest favourite
Guesthouse in Ashland
4.91 out of 5 average rating, 11 reviews

Tolman Creek Suite/Forest Canyon Suite

KatieRating, 5 stars5 days ago
Such a lovely garden getaway!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Central Point
4.95 out of 5 average rating, 586 reviews

The Hygge Stay in the Heart of Southern Oregon

AlexisRating, 5 stars3 weeks ago
Bryanna's place is spotless, very beautifully decorated and spacious. There were all the amenities that are shown in the photos. She was friendly, flexible, and responsive about checkin. Very minor, but the bed pillows were extremely flat and the twin beds not the most comfortable. All in all a great stay, if a bit pricey for the area.
Guest favourite
Guesthouse in Medford
4.89 out of 5 average rating, 91 reviews

Near Downtown- Kitchen-Washer/Dryer-Parking

HanaRating, 5 stars1 month ago
Ubytování hezké, klidné, výborně vybavené. V okolí jsme se cítili bezpečně. Určitě doporučuji.
Guest favourite
Guesthouse in Medford
4.91 out of 5 average rating, 22 reviews

New build in East Medford with pool & hot tub

KateRating, 5 stars3 weeks ago
Great stay with a beautiful private pool and hot tub. Finishes inside were top notch - gave me ideas for my own kitchen. Potential guests should know the bedroom is upstairs while the bathroom is on the main floor down a flight of wooden stairs - something to keep in mind if you have balance issues in the middle of the night. A lovely place for a getaway in Medford.
Guest favourite
Guesthouse in Central Point
5 out of 5 average rating, 17 reviews

Spacious Cottage w/King Bed, Fireplace, 65" TV

EshaRating, 5 stars1 month ago
We had a great stay at this AirBnb. The location was convenient (near family). The place was clean and relatively baby/toddler friendly. I liked the separate room for kids so that we could still be up a bit once we put the our kid down. The bed was comfortable, and everything seemed new and very clean. They’ve thought of just about everything you could need in the kitchen, bathroom, etc. One thing to note is that check in is a little later and check out is earlier than typical so plan for that. Our only issue was a chicken coop outside and a rooster crowing at odd hours (11pm, 4am, etc) waking our family up. I recommend bringing a sound machine or the host adding a purifier or something to drown that out. Overall, we thought this place was lovely and will likely stay here when we visit family again!
Top Guest favourite
Guesthouse in Grants Pass
4.95 out of 5 average rating, 58 reviews

Spectacular Rogue River views & charm!

Kristen HansenRating, 5 stars2 weeks ago
This rental was nicer looking then the photos - tastefully decorated and nice large rooms. The river view was amazing. We enjoyed watching the ducks and geese float in the river while having a glass of wine on the patio. The neighborhood is not fancy, but the house and view are very nice. We walked to the Rivers' Edge restaurant and enjoyed that as well - lovely view and patio with good food.
Top Guest favourite
Guesthouse in Grants Pass
4.98 out of 5 average rating, 242 reviews

Sand Creek Cottage

RobinRating, 5 stars1 month ago
This little barn is fixed up so nice. The bed was very comfortable and the place was quiet and secure. I loved all the extra touches..fresh eggs! It is more beautiful than the photos and super clean.
Top Guest favourite
Guesthouse in Medford
4.94 out of 5 average rating, 31 reviews

Cozy home in Medford”

SarahRating, 5 stars3 weeks ago
This is our second time staying at Angelica's cozy home, and I know it won't be our last. We have a soccer tournament every year in Rouge Valley and Angelica's house is the perfect location for all the games, and is the perfect spot for relaxation between the busy tournament schedule. The house is cozy and has everything you need. Angelica is a great host. She is responsive and we look forward to future stays.
Top Guest favourite
Guesthouse in Grants Pass
4.99 out of 5 average rating, 100 reviews

1 BDRM Cottage-Keyless self check in-Quiet Lane

CathyRating, 5 stars1 week ago
This was our second stay at Natalie’s cottage and it was as wonderful as the first stay. The cottage is lovely, very private and right in town. We enjoyed every minute of our stay and look forward to our next visit.

Quick stats about guesthouse rentals in Ashland

  • Total rentals

    20 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    3K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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