Guesthouse vacation rentals in Ashland

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Top-rated guesthouse rentals in Ashland

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

Guest favorite
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
Nov 20 – 27
$148 per night
4.97 out of 5 average rating, 422 reviews
Guest favorite
Guesthouse in Ashland
The Cedar Cottage - creekside studio
This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!
Sep 22 – 29
$92 per night
4.94 out of 5 average rating, 100 reviews
Guest favorite
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.
Apr 20 – 27
$115 per night
4.98 out of 5 average rating, 502 reviews

Popular amenities for Ashland guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Central Point
BEE WELL Organic Spa Garden Studio
May 30 – Jun 6
$84 per night
4.94 out of 5 average rating, 688 reviews
Guest favorite
Guesthouse in Ashland
Comfortable, Private Guest Lodging
Jun 23 – 30
$104 per night
4.95 out of 5 average rating, 311 reviews
Guest favorite
Guesthouse in Medford
The Greenwood Villa
Apr 27 – May 4
$177 per night
4.92 out of 5 average rating, 343 reviews
Guest favorite
Guesthouse in Medford
Comice Valley Inn (Sanitized Daily)
Nov 14 – 21
$87 per night
4.98 out of 5 average rating, 425 reviews
Guest favorite
Guesthouse in Grants Pass
Queen Lady Vacation Rental pet friendly.
Jul 27 – Aug 3
$96 per night
4.96 out of 5 average rating, 339 reviews
Guest favorite
Guesthouse in Grants Pass
Sweet Vintage Cottage steps from Rogue River
Apr 16 – 23
$99 per night
4.94 out of 5 average rating, 427 reviews
Guest favorite
Guesthouse in Medford
Lotus 2-Peaceful-Central Location-W/D-Walk to Park
Jan 13 – 20
$99 per night
4.85 out of 5 average rating, 118 reviews
Guest favorite
Guesthouse in Medford
Roxy Ann Retreat - Large Luxury Carriage House
Feb 3 – 10
$98 per night
4.95 out of 5 average rating, 66 reviews
Superhost
Guesthouse in Medford
Million Dollar View No city tax! Huge 4k tvs
May 16 – 23
$113 per night
4.68 out of 5 average rating, 99 reviews
Guest favorite
Guesthouse in Gold Hill
Rogue River Guesthouse: Rural river views near I-5
Aug 9 – 16
$223 per night
4.98 out of 5 average rating, 83 reviews
Superhost
Guesthouse in Medford
Next to airport/expo safe parking! Modern lodging
Dec 7 – 14
$106 per night
4.87 out of 5 average rating, 99 reviews
Guest favorite
Guesthouse in Medford
Private guesthouse
Mar 19 – 26
$99 per night
4.88 out of 5 average rating, 106 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
Apr 18 – 25
$146 per night
4.98 out of 5 average rating, 107 reviews
Guest favorite
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Sep 24 – Oct 1
$193 per night
4.95 out of 5 average rating, 116 reviews
Guest favorite
Guesthouse in Ashland
The Poets' Inspiration Cottage
Aug 6 – 13
$126 per night
4.94 out of 5 average rating, 36 reviews
Guest favorite
Guesthouse in Ashland
Countryman-Fox Carriage House
Dec 29 – Jan 5
$125 per night
5.0 out of 5 average rating, 44 reviews
Guest favorite
Guesthouse in Ashland
C Street Station Cottage
Nov 15 – 22
$189 per night
5.0 out of 5 average rating, 74 reviews
Guest favorite
Guesthouse in Ashland
Casa Amore Cottage: Walkable and pet friendly!
Feb 4 – 11
$103 per night
4.8 out of 5 average rating, 10 reviews
Guest favorite
Guesthouse in Medford
Adorable guest house with hot tub.
Jan 25 – Feb 1
$102 per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Guesthouse in Jacksonville
La Petite Maison + Spa
Dec 6 – 13
$162 per night
4.94 out of 5 average rating, 62 reviews
Guest favorite
Guesthouse in Jacksonville
Serenity Canyon Cottage
Jun 10 – 17
$75 per night
4.96 out of 5 average rating, 24 reviews
Guest favorite
Guesthouse in Grants Pass
Spacious upstairs studio with kitchenette & 1 bath
Mar 28 – Apr 4
$83 per night
4.98 out of 5 average rating, 63 reviews
Guest favorite
Guesthouse in Jacksonville
Chamomile Cottage
May 17 – 24
$126 per night
5.0 out of 5 average rating, 64 reviews
Guest favorite
Guesthouse in Ashland
Silver Frog Guesthouse- downtown Ashland 'hood
Sep 20 – 27
$147 per night
4.92 out of 5 average rating, 25 reviews

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Ashland
Manzanita Cottage
Sep 3 – 10
$162 per night
4.97 out of 5 average rating, 143 reviews
Guest favorite
Guesthouse in Medford
The Loft at Highcrest
Jul 6 – 13
$90 per night
4.97 out of 5 average rating, 127 reviews
Guest favorite
Guesthouse in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
Nov 13 – 20
$125 per night
4.94 out of 5 average rating, 109 reviews
Guest favorite
Guesthouse in Medford
Modern, pet-friendly, private - EV charger level 2
Jan 8 – 15
$85 per night
4.94 out of 5 average rating, 141 reviews
Guest favorite
Guesthouse in Central Point
Southern Comfort - Hot tub - Modern - Relaxing
Jul 28 – Aug 4
$139 per night
4.92 out of 5 average rating, 126 reviews
Guest favorite
Guesthouse in Central Point
Hygge Stay. Pet friendly* private and cozy.
May 26 – Jun 2
$142 per night
4.96 out of 5 average rating, 498 reviews
Guest favorite
Guesthouse in Medford
Newer, quiet, private cottage
May 1 – 8
$91 per night
4.99 out of 5 average rating, 193 reviews
Superhost
Guesthouse in Ashland
East Main Downtown Bungalow
Dec 6 – 13
$159 per night
4.76 out of 5 average rating, 80 reviews
Guest favorite
Guesthouse in Ashland
Guesthouse in Ashland 4 blocks from the OSF
Sep 27 – Oct 4
$158 per night
5.0 out of 5 average rating, 28 reviews
Guest favorite
Guesthouse in Grants Pass
1 BDRM Cottage-Keyless self check in-Quiet Lane
Jun 8 – 15
$81 per night
4.98 out of 5 average rating, 60 reviews
Guest favorite
Guesthouse in Medford
Full Kitchen-Washer/Dryer- Near Downtown-Parking
Oct 22 – 29
$78 per night
4.89 out of 5 average rating, 37 reviews
Guest favorite
Guesthouse in Eagle Point
Deer Ridge Guesthouse
Mar 18 – 25
$68 per night
4.83 out of 5 average rating, 6 reviews

Quick stats about guesthouse rentals in Ashland

Total rentals

30 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

3.3K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

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