Guesthouse vacation rentals in Ashland

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Top-rated guesthouse rentals in Ashland

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Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 471 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

Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 645 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.

Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 454 reviews

Comice Valley Inn (Sanitized Daily)

Health care professionals please ask about special rate for longer term rental. We disinfect all surfaces before and after new guests arrive. Rest assured. Comfortable, light, clean and airy private two bedroom upstairs guesthouse. Host on location in separate home. Fully equipped kitchen, with breakfast provided, makes this the perfect place for overnight or an extended stay. Neighborhood is quiet and shopping and dining are not far away. Two bedrooms make this a perfect getaway for friends.

Guest favorite

Guesthouse in Central Point

4.92 out of 5 average rating, 150 reviews

Hot tub - Modern - Relaxing - Private - Clean

Our cozy, modern guest house is light, open and spacious. It is approximately 650 sq ft with Hot Tub, 1 queen bedroom, a cozy upstairs loft with a double bed. The bathroom has a walk in shower, washer & dryer. Fully equipped kitchen that flows into the dining and living room. Off the dining area is a private yard with patio, hot tub, outdoor shower, BBQ, chairs and table . Our guest house is located behind a detached shop so you'll have a private entrance & convenient parking and privacy.

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 555 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.

Guest favorite

Guesthouse in Eagle Point

4.9 out of 5 average rating, 285 reviews

Free Bird Ranch-Oregon Adventures Home Base

You’ll love the peace and serenity this private guest house brings! We are minutes away from beautiful vineyards. On the path- (50 minutes) to CRATER LAKE where you can sightsee, hike, and snow shoe. Go fishing on the Rogue 5 minutes away! Enjoy the deck that overlooks the views of the valley and view’s of the CASCADES AND TABLE ROCK which is a 5 minute drive to the entrance. Ashland ski resort is 45 minutes away. Come back to a relaxing and cozy home after your adventures in the Rogue!

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 111 reviews

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.

Guest favorite

Guesthouse in Grants Pass

4.96 out of 5 average rating, 356 reviews

Queen Lady Vacation Rental pet friendly.

Awestruck is not nearly enough to describe what you feel when you see our 1905 Colonial revival home. We have worked tirelessly to restore this home to its original charm. The main rental unit is a private restored two bedroom Carriage house that is fully air conditioned with an open floor plan. We are less than 1 mile from town but still enjoy watching deer families and wild turkeys cross our property. It truly is a home away from home and a clean comfortable place to relax in.

Guest favorite

Guesthouse in Medford

4.96 out of 5 average rating, 314 reviews

Cabo Cottage, private guest house.

Discover the charm of this inviting 2-bedroom, 1-bath guest house nestled in a quiet neighborhood, conveniently situated just minutes away from essential amenities, and 15 min from airport, and 6-10 min from local hospitals. Equipped with a well-appointed kitchenette, and washer/dryer for added convenience. The master bedroom features a king-size memory foam bed, while the second bedroom has a queen bed. Enjoy a private driveway and entrance. Extended stay discounts available.

Guest favorite

Guesthouse in Medford

4.88 out of 5 average rating, 111 reviews

Loft Near Downtown-Studio-Parking -Kitchenette-

Adorable upstairs guest studio apartment. Perfect location within walking distance to downtown, restaurants, farmer's market, shopping, hospitals, park, movie theater & bus lines. Apartment access & private off street parking from the rear alley. This studio includes full bathroom with tub/shower, kitchenette, queen bed, 2 chairs & a large SmartTV Stocked Kitchenette includes mini a fridge, sink, microwave, & supplies for coffee/tea. ***STAIRS REQUIRED***

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 168 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)

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 750 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

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!