Holiday rentals in Ashland

4.96 out of 5 average rating, 170 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

Guest house in Lithia Park

4.99 out of 5 average rating, 595 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 house in Lithia Park

4.99 out of 5 average rating, 172 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, 130 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, 249 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, 423 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, 173 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, 398 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!

4.95 out of 5 average rating, 677 reviews

Flat in Ashland

Swank House -Downtown Suite- Pet Friendly

Walk to all the shops, theaters, restaurants, trails and more. Steps to DOWNTOWN Ashland. All recently updated, this space brings in modern luxury design, travel convenience and location, location, location! New king bed surrounded with LED lighting, soft rugs, and plush bedding. Private parking eliminates all those downtown parking restrictions and time limitations. Pets welcome. Maximum 1 with pet fee. (#18-243)

4.9 out of 5 average rating, 114 reviews

Guest suite in Ashland

Summer’s Night Cottage 8 minute walk to Downtown

Clean and comfortable cottage perfect for a getaway. Short distance to downtown Ashland, Lithia Park, Oregon Shakespeare Festival, and more. Great outdoor space. Relax in our clean 1 bedroom cottage with a newer queen bed, high thread count sheets, and convertible full size sofa, sleeping area. Walk to one of the many restaurants & bars or fix a simple meal with provided hot plate and kitchen basics.

Superhost

Dome in Ashland

4.79 out of 5 average rating, 100 reviews

The Acorn dome

Nestled in the trees, the geodome has mini split ac, heat, WiFi, tv, kitchen area, stove, fridge and private detached bathroom/shower. Three miles to Ashland, yet surrounded in nature. Take advantage of the Incredible views and bird watching on the wrap around deck. Barrel sauna available for use, shared with adjacent tiny house airbnb

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Popular amenities for Ashland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Ashland

4.97 out of 5 average rating, 470 reviews

Cottage in Lithia Park

Victorian Garden Carriage House

AnnaRating, 5 stars1 week ago

I had a wonderful time at the carriage house. Margaret has put a lot of attention into the details to make this a very comfortable and enjoyable place to stay. I could happily live there. Our hosts were delightful, accessible, and made us feel quite welcome. It was great to be at a location where we could park our car and walk to restaurants, Lithia Park, and the OSF. The garden was a treat and a delightful place to relax. I hope to be lucky enough to book it on my next visit to Ashland!

4.93 out of 5 average rating, 730 reviews

Farm stay in Ashland

Kelly’s Farm 4 miles to Ashland

KellyRating, 5 stars3 days ago

Stayed in June to watch 4 plays at OSF. Perfect location to relax, get away from tourist bustle of town. Extremely easy and fast coming and going to Ashland. Appreciated the hosts food recommendations. Beautiful weather and quiet farmland. Enjoyed it!

4.88 out of 5 average rating, 795 reviews

Flat in Lithia Park

Clean, Stylish Apt w/kitchen. block from Downtown

JjRating, 5 stars1 week ago

We have been staying here for years, and this is THE perfect spot for a getaway weekend to watch plays. A short walk to the shows, breakfast down the hill, high tea a block away. The room is spotless and the full kitchen is a blessing.

5 out of 5 average rating, 8 reviews

Home in Ashland

Grandview of Ashland | Hot tub | Sauna | Firepit

MikeRating, 5 stars1 week ago

We couldn't get over the stunning views and sunsets from this cabin high above Ashland. Yet it's an easy drive or a nice walk into town. This recent remodel is beautifully done. We loved the front porch and gas fir pit to sit outside and enjoy the quiet evenings. Loved the wildlife (birds and deer) around the house too. Getting there will seem a little confusing at first following some dirt roads, but the owners have a well maintained paved driveway on the last segment to the house. This is a very special spot.

4.96 out of 5 average rating, 27 reviews

Apartment 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, 127 reviews

The Birdhouse Retreat| Views & Hot Tub

KimRating, 5 stars5 days ago

Agnes's place was so relaxing and comfortable and we loved their recommendations of local places to visit.

4.98 out of 5 average rating, 170 reviews

Home in Ashland

Creekside Retreat Close to Town

AnneRating, 5 stars3 weeks ago

This is our third year staying at Sari and Jacks home, we couldn’t recommend it enough! We find new little touches and comforts each time, and our young daughters love seeing cows out the window every morning. Sari and Jack are responsive and funny. Space is clean, welcoming, and has everything our family needs!