
Guest house holiday rentals in Ashland
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Top-rated guest house rentals in Ashland
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

Mel-Ohana: your favorite country retreat!
Mel-Ohana is a quiet, private two bedroom, 1 bath upstairs unit with comfortable queen memory foam mattresses, kitchen amenities, and a beautiful large bathroom with tiled shower. Open, bright and airy, the country views are spectacular from both bedrooms. It's the perfectly-placed retreat, with Jacksonville/Britt 5 mins away, Ashland -25 mins., and 12 mins. from Medford shopping and restaurants. Wander the 1/2 acre lawn and garden area or share a bottle of wine on the ground-level cedar deck!

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

The Greenwood Villa w/wood fire hot tub
The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

Orchard Home Cottage * ~ Private, Cozy, Peaceful *
*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

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!

Countryman-Fox Carriage House
Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

C Street Station Cottage
Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

Cozy Jacksonville Cottage
This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Mindy’s Ashland Hideaway
Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

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 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.

Manzanita Cottage
Enjoy staying in this newly-constructed cottage in the heart of Ashland's historic railroad district. Park your car and enjoy all that Ashland has to offer by foot. Easy walking distance to downtown shops and restaurants, OSF, Lithia Park and the Ashland Food Coop. Outdoor enthusiasts can start their mountain biking, running or hiking adventures right from their door. Your hosts can help to point you in the right direction. (Permit #: PA-2018-00531)

Chalet in the Woods
Welcome to the little Chalet in the beautiful Oregon woods! Come relax and unplug in this charming private guest house situated on 4 acres, just 5 minutes from downtown Grants Pass and 3 minutes from grocery stores and shopping yet you feel as if you are out in the country far removed from anything and everything. This space was created to embody Swiss style living and the details speak to that. Comfortable and efficient.
Popular amenities for guest house rentals in Ashland
Family-friendly guest house rentals

The Peaceful Log Room: 1 Bedroom Guesthouse

Dream Cottage on the Rogue River

Carter Lane Cottage

Close to Downtown Grants Pass Everything you Need!

Million Dollar View No city tax! Huge 4k tvs

Laurel Farm's Guesthouse

The Nest at Highcrest

Adorable guest house with hot tub.
Guest house rentals with a patio

Hanna's House by WanderLodges |1 block to downtown

La Petite Maison + Hot Tub

Spectacular Rogue River views & charm!

Sunflower

Peaceful Countryside Stay with Scenic Views

New Modern Cottage on the Rogue

2 Bedroom Carriage house

Courtside Cottage - WalkScore 93 - Dog Friendly
Guest house rentals with a washing machine and dryer

The Hygge Stay in the Heart of Southern Oregon

Sand Creek Cottage

Modern Guest House w/ Hot Tub, Loft & Fenced Yard

JJ's Loft | Downtown | Large Deck | Kitchenette

1 BDRM Cottage-Keyless self check in-Quiet Lane

East Main Downtown Bungalow "C"

Historic carriage house close to downtown Ashland

Historic Cottage close to plaza
Quick stats about guest house rentals in Ashland
Total holiday rentals
Explore 20 holiday rentals in Ashland
Nightly prices starting at
Ashland holiday rentals start at £37 per night before taxes and fees
Verified guest reviews
Over 3,470 verified reviews to help you choose
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 of Ashland holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals
4.9 Average rating
Ashland stays are highly rated by guests – averaging 4.9 out of 5!
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