Holiday houses in Ashland

4.96 out of 5 average rating, 169 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.

4.98 out of 5 average rating, 501 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

Treehouse in Jacksonville

4.98 out of 5 average rating, 259 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

4.99 out of 5 average rating, 594 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.

4.99 out of 5 average rating, 170 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.

5 out of 5 average rating, 129 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.

4.98 out of 5 average rating, 247 reviews

Farm stay in Ashland

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

4.95 out of 5 average rating, 419 reviews

Cabin in Ashland

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

4.98 out of 5 average rating, 171 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)

4.9 out of 5 average rating, 396 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!

4.96 out of 5 average rating, 116 reviews

Ashland Artist Country Retreat

Lovely light-filled, artistic, private, quiet, two-level studio apartment with full bath and kitchenette located on an organic farm in a beautiful country setting, just 3.6 miles to downtown Ashland and the Oregon Shakespeare Festival. Enjoy a private garden and views of the trees and mountains, as well as original art made by your host. We offer organic and upscale amenities and use only eco-friendly and healthy cleaners.

4.88 out of 5 average rating, 794 reviews

Apartment in Ashland

Clean, Stylish Apt w/kitchen. block from Downtown

92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines.

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Ashland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Ashland

5 out of 5 average rating, 11 reviews

Hanna's House by WanderLodges |1 block to downtown

IreneRating, 5 stars1 week ago

As advertised! Hanna’s house was in a terrific location (VERY walkable to all the things, but tucked away enough that I heard no noise at night), and every thoughtful detail accompanied this Airbnb. Loved it.

Superhost

4.91 out of 5 average rating, 150 reviews

The Cedar Cottage - creekside studio

RoseRating, 5 stars2 weeks ago

Very beautiful quiet setting with relaxing back patio with a stream. Very cozy cabin, and close to town.

4.93 out of 5 average rating, 726 reviews

Farm stay in Ashland

Kelly’s Farm 4 miles to Ashland

NainaRating, 5 stars2 days ago

I stayed here for a night with my dog. Kelly and Chace went above and beyond to be gracious and accommodating. They even allowed me an early check in to join some online meetings. The space is beautiful and so peaceful. My dog loved hanging out in the yard and I slept like a baby in the comfy owls nest. The deck was perfect for catching a gorgeous sunset. We definitely hope to go back!

4.9 out of 5 average rating, 112 reviews

Guest suite in Ashland

Summer’s Night Cottage 8 minute walk to Downtown

JeanetteRating, 5 stars2 weeks ago

As when I stayed here last year with a friend, Eric proved to be a very accommodating host. The place is small with a limited kitchen but ample for simple meals and a cozy stay. I am a walker and appreciate that the location makes for a pleasant ramble through a residential neighborhood to downtown or a detour to the upper end of Lilith Park. I also love sitting, eating, and relaxing in the garden area.

4.96 out of 5 average rating, 27 reviews

Condo in Ashland

Plaza North Suite 203 Windsor

KelleyRating, 5 stars1 month ago

We visit Ashland regularly to visit family. I’ve traveled a lot, and this was one of those rare good finds. The host is wonderful, and so is the place. I loved the modern, minimalist, yet natural and warm interior and it’s very convenient (the Co-Op, etc). It was very quiet, too. We’d stay here again in a heartbeat.

Guest suite in Jacksonville

4.9 out of 5 average rating, 125 reviews

The Birdhouse Retreat| Views & Hot Tub

ElizabethRating, 5 stars1 week ago

Agnes and Aaron were marvelous hosts and very accommodating. They were super responsive and made check-in and check-out easy. The views of the Siskiyou Mountains are stunning and can be enjoyed from the balcony, hot tub, and cute kitchen table. Would absolutely recommend and visit again.

4.95 out of 5 average rating, 95 reviews

Home in Ashland

The Aloha House - Hot Tub - Pool

ReneRating, 5 stars3 days ago

Google maps took us right to the location which was great. Kyle was kind to greet us and show us the ropes. We were able to relax and enjoy all the place has to offer for a couple of days. Comfortable beds, pillows, and linens. Kitchen stocked with so many items. Clear instructions for all the things you’d need them for. Lovely stay!