Guesthouse vacation rentals in Ashland

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Top-rated guesthouse rentals in Ashland

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Top guest favorite

The exterior of the unit is shown, featuring a private deck with seating and a view of the surrounding greenery. A well-maintained lawn is visible, along with flower beds and mature trees, which enhance the tranquil country setting.

Guesthouse in Medford

4.97 out of 5 average rating, 288 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!

Top guest favorite

The spacious studio features large windows, allowing natural light and showcasing views of mountains. A queen size bed is complemented by sitting areas with a television and coffee table. A dining bistro table neatly fits in the corner, enhancing the open layout.

Guesthouse in Ashland

4.96 out of 5 average rating, 181 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.

Top guest favorite

The exterior of The Ashland Cottage is shown, featuring a welcoming sign amidst lush greenery. The cottage’s blue siding and distinctive architectural details are highlighted, while a paved walkway leads to the front entrance, framed by natural foliage.

Guesthouse in Ashland

4.97 out of 5 average rating, 516 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

Top guest favorite

An airy living space is highlighted by large windows that provide abundant natural light and views of the surrounding landscape. A wooden ladder leads to a loft area, while minimal furnishings, including a cozy sofa and a wooden table, create a serene atmosphere.

Guesthouse in Medford

4.93 out of 5 average rating, 412 reviews

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

Guest favorite

The charming exterior of a vintage guest cottage is highlighted, featuring warm wooden siding and green-framed windows. Soft lighting from hanging bulbs creates a welcoming ambiance, while potted plants and rustic barrels add natural elements to the entrance.

Guesthouse in Ashland

4.92 out of 5 average rating, 167 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!

Top guest favorite

The entrance to the cottage is framed by a rustic trellis and surrounded by lush greenery. A wooden deck leads up to a white door, providing a welcoming access point. Sunshine filters through the leaves, adding a natural brightness to the scene.

Guesthouse in Lithia Park

5 out of 5 average rating, 201 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.

Top guest favorite

The studio features an open layout with a king bed and a cozy seating area. A flat screen TV is positioned near the fireplace. Natural light streams through multiple windows, illuminating the kitchenette and dining area, which are adjacent to a private outdoor space.

Guesthouse in Ashland

5 out of 5 average rating, 145 reviews

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.

Top guest favorite

An inviting outdoor patio area is surrounded by greenery, featuring a round table with a floral tablecloth and two green chairs. A large red umbrella provides shade. The cottage's door is framed by a vibrant window box filled with flowers, contributing to a charming ambiance.

Guesthouse in Jacksonville

4.93 out of 5 average rating, 1,095 reviews

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.

Guest favorite

The exterior of a guest house is shown, featuring a light yellow facade and large windows. A deck with white chairs and a table is visible, surrounded by green grass and landscaping stones. A flowering tree provides shade, complementing the serene outdoor space.

Guesthouse in Ashland

4.87 out of 5 average rating, 102 reviews

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!

Top guest favorite

A spacious living room is presented with stylish furnishings, including a gray sofa and a patterned area rug. Natural light filters through the large windows. A spiral staircase leads to the loft above, while double doors open to the outdoor space.

Guesthouse in Lithia Park

4.99 out of 5 average rating, 619 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 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.

Top guest favorite

A charming entrance features a bold red door and two red metal chairs situated at a small table, surrounded by gravel and greenery. A modern light fixture is mounted beside the door, adding a welcoming touch to the exterior.

Guesthouse in Ashland

4.98 out of 5 average rating, 193 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

A stone pathway leads through a lush garden filled with vibrant flowers, including pink roses, towards a charming cottage. The garden is surrounded by greenery and features an archway, adding a picturesque framing to the entrance.

Guesthouse in Ashland

4.9 out of 5 average rating, 411 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!