Guesthouse vacation rentals in Ashland

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Top-rated guesthouse rentals in Ashland

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Guest favorite

Guesthouse in Ashland

4.94 out of 5 average rating, 123 reviews

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.

Dec 16 – 23

G$42,172 GYD per night

Guest favorite

Guesthouse in Medford

4.97 out of 5 average rating, 234 reviews

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!

Sep 17 – 24

G$19,620 GYD per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 434 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

Oct 26 – Nov 2

G$34,696 GYD per night

Guest favorite

Guesthouse in Central Point

4.97 out of 5 average rating, 887 reviews

The West Wing Guest House

Located next to the main home, this detached guest house has a separate driveway/parking & hosts kitchen/living downstairs, with bedroom & bathroom upstairs. We are located 5 miles from Jacksonville, home of the Britt Festival & the best local wineries. About 20 minutes south is the town of Ashland, well known for the Shakespeare Festival. Downtown Central Point is just a mile away, where you will find the renowned Rogue Creamery. The house is also only 10 minutes from the Rogue Valley Airport.

Jul 20 – 27

G$15,418 GYD per night

Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 583 reviews

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.

Jun 21 – 28

G$19,822 GYD per night

Guest favorite

Guesthouse in Ashland

4.94 out of 5 average rating, 107 reviews

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!

Jan 21 – 28

G$22,086 GYD per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 512 reviews

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.

Dec 16 – 23

G$28,591 GYD per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 183 reviews

Wood Hamlet - Picasso Cottage by Downtown, kitchen

Our 'Picasso Cottage' sleeps up to 2 adults and is perfect for those who wish to enjoy artful living close to downtown Ashland! The space is the entire bottom floor of Carriage House, with full bathroom, bedroom (queen bed) with sitting area, washer/dryer, living room and full kitchen. Between shows relax on patio or by the swimming pond in garden. Private parking behind Carriage House. Walk to theater! (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Aug 8 – 15

G$25,407 GYD per night

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 709 reviews

BEE WELL Organic Spa Garden Studio

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

Jul 22 – 29

G$23,169 GYD per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 143 reviews

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)

Nov 11 – 18

G$38,957 GYD per night

Guest favorite

Guesthouse in Ashland

4.9 out of 5 average rating, 340 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

Oct 14 – 21

G$29,805 GYD per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 155 reviews

Starthistle Cottage in Applegate wine country

Rural cottage in the beautiful Applegate Valley. Peaceful with beautiful views of the landscape and wildlife. Closest lodging to Woodrat Mountain launch for paragliders & hang gliders. Nestled in the heart of the Applegate Wine Trail and the Southern Oregon Lavender Trail. Close to historical Jacksonville for the Britt Festival. Easy access to Applegate Lake and surrounding hiking trails.

Mar 14 – 21

G$21,791 GYD per night