Home Vacation Rentals By Owner In Ashland, OR

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Exceptional(4)

$1029.02

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Villa

Luxury Ashland Mountain Escape: Pool, Hot Tub

Ashland, Oregon, United States

Summary:brbrLive the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways or small gatherings.brbrTake in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature.brbrPlay games on the lawn, read by the living room fireplace, or try your hand at the billiards table. brbrThe kitchen is fully equipped to live out all your entertaining dreams, and a screened sun porch provides the perfect setting for late afternoon noshes and nibbles. A Swank House property.brbrbrbrThe Space:brbrTHE SPACEbrbrJefferson Estate is a four bedroom, single-level home that’s ideal for family getaways, girls’ weekends, book clubs, weddings, and reunions. Twelve people sleep comfortably, and sleeping pads are available for crashing by the gas fireplace or out on the screened patio.brbrThe generous open living spaces welcome you and your guests to relax, entertain, eat, drink, play games and enjoy good company. Our biggest hope is that you’ll make yourself comfortable in this luxurious home away from home.brbrbrbrGuest Access:brbrYou have the place to yourself.brbrbrbrThe Neighborhood:brbrLocated on 8 acres yet only 3 miles to Oregon Shakespeare Festival. Jefferson Estate is close in and private for your whole group. Please note that you may see our horse staff off in the distance training or giving lessons in the horse arena. The residence is located at the back of the property with gate access only to the home.brbrbrbrGetting Around:brbrJefferson Estate sits conveniently just minutes from the South Ashland I-5 freeway entrance (although you’ll feel like you’re miles away from anyone). It’s really the best of both worlds — you’ll feel like you are in the country, but only steps away from the action of downtown Ashland’s famous food and theatre scene.brbrWe’re also just a few minutes from Emigrant Lake, and several local wineries. In fact, you can walk to Weisinger Family Winery (about .5 miles away), and drive to Irvine and Roberts tasting room (a favorite!) in a matter of minutes. brbrThis home is approximately 8-minutes from downtown Ashland’s Plaza and the Oregon Shakespeare Festival theatre.brbrbrbrOther Things to Note:brbrA note for families with littles: the pool, hot tub and pond are not fenced-in from the rest of the property. Please be extra attentive with small children around this home’s open bodies of water.brbrNo Swimming in the pond. brbrBring your own fishing poles for bass and bluegillbrbrbrbrInteraction with Guests:brbrWe take your privacy very seriously and do not intrude on your vacation. However, if you need any assistance, we are here to help and are always available by text.
Bed 4

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Bath 4

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Sleep 12

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Exceptional(109)

$178.4

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Cottage

Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248)

Ashland, Oregon, United States

Whimsical and comfortable cottage located off a quiet alley behind our main residence. You will experience a low-key, friendly neighborhood in the heart of Ashland's Skidmore Historic District. Private garden area with back patio, outside dining for two. You can park your car and never get back in until it's time to leave. Just a 5-10 minute stroll the Ashland Co-op, restaurants, and of course Oregon Shakespeare festival.brbrFull kitchen and laundry. Along with the queen bed there is a single bed in the nook off the living area for a 3rd person or for those who prefer to sleep separately. The closet has lots of shelving to store your things. Bathe in the claw-foot tub or use the shower. Heat and AC keeps things comfortable. This is a light-filled groovy hideaway.brbrParking is out on the street about 200 feet from the cottage.brbrMonthly rentals are not available except in rare circumstances and only for one person. Rate will not be significantly reduced.brbrEloise:brWe have a very friendly Labrador who lives on the property. Although the yards are separated by a gate, there may be some coming and going of Eloise, and you are likely to encounter her. If you do not like dogs or are not comfortable with them, this is probably not the place for you.brbrAccording to Google Maps, the distance to the OSF box office downtown is .6 miles and the walk should take approximately 10 minutes.brbrLicensed with City of Ashland (PA-2017-00248) Registration #BL-009768
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Sleep 3

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Exceptional(1)

$184.73

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Castle

Chateau Herbe - Shakespeare 1 Bedroom Suite w/ Kitchen

Ashland, Oregon, United States

Welcome to the Shakespeare Suite at Château HerbebrA serene escape nestled within a modern-day castle estatebrbrPerched on the two floors of the grand Château Herbe, the Shakespeare Suite offers an enchanting stay surrounded by timeless beauty and peaceful charm. From your private balcony, take in sweeping views of the estate’s classical gardens, the rolling vineyards, and the majestic Rogue Valley stretching toward the distant mountains.brbrInside, the suite features a full kitchen equipped for culinary inspiration, a spacious living and dining area for relaxed gatherings, and elegant furnishings designed for comfort and style. This tranquil retreat is just minutes from I-5 and the heart of downtown Ashland, offering both convenience and seclusion.brbrYour Experience Includes:brbrAccess to the château’s welcoming communal spaces, including a sun-drenched sunroom, curated library, charming coffee bar, and a gracious outdoor patiobrbrStrolling privileges through the estate’s picturesque grounds: wander among vineyards and orchards, linger beneath the pergola by the pond, and pause to admire the classical fountainbrbrRejuvenation in the château’s hot tub and sauna, located just to the left of the sunroom in the main chateau.brbrPlease note, Château Herbe is home to other guests and residents who share the grounds and common areas respectfully.brbrShould you need anything during your stay, your host is readily available via messenger or phone to ensure your experience is nothing short of exceptional.brbrLet the Shakespeare Suite be your haven of calm and beauty—where every sunrise feels like poetry, and every evening is a gentle retreat.
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Sleep 4

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Exceptional(59)

$311.35

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Private Vacation Home

Mt Ashland Homestead, Ashland 10m, 40 ridgetop acres old forest, right by PCT

Ashland, Oregon, United States

Beautiful, large architectural home nestled in the Siskiyou/Cascade Mountain forests of Southern Oregon. About 15 minutes to downtown Ashland, 20 minutes to Mt. Ashland Ski Area and alpine hiking, and a three minute walk from the front door to the Pacific Crest Trail with meadows, forest and ridges looking out to many mountain ranges. This home is a peaceful, quiet, and beautiful getaway: close enough to Ashland to be convenient, yet surrounded by old forest and mountains and right on top of Siskiyou Summit. You'll the way the natural light floods the house with s feeling of being out in nature even when you're inside! Features fully equipped kitchen and dining (both formal and informal), two large, open living rooms, large sun room and two-person Ofuro hot tub overlooking the forest, 2-car garage, seasonal Swedish sauna house, and walking trails. For children, If you would like a full-size crib and high chair, please let us know. Kids call it 'the adventure house' and there is plenty of room to play indoors and out. Outdoor play structure, paved drive for bikes, lots of nature to explore.brbrConcerns: We don't have any bears or mountain lions in this neck of the woods, so an evening stroll to watch the sunset is quite safe. We are above the elevations where poison oak grows. No one has ever gotten a tick on them, not even ourselves when we are doing work on the land. If ever needed, it takes the ambulance 10 minutes to arrive at the house (really!).br Families and couples often spend weeks here, working remotely and enjoying nature during all the seasons. Professional companies have also found it a beautiful place for a work retreat (usually renting the log house as well). We have excellent Starlink satellite internet (faster than in town) and cell phone reception is always very good. Callahan's Restaurant is a mile away, providing breakfast, lunch and dinner is you'd like easy access to a nearby dining.br The town of Ashland is home to the renowned Shakespeare Festival. Smaller theater companies are also quite good. Being a thriving tourist town, restaurants are outstanding, nearly mind-boggling in number and variety, making exploration fun. brChildren really enjoy the ScienceWorks Museum, Lithia Park and Wildlife Images. Children also enjoy riding their bikes (and little training bikes) on our long paved driveway, catching frogs by the pond, having 38 acres to explore safely. Sledding and building ice caves in the winter is fun! We recently built a big play structure with swings, slides, a little kitchen, climbing.br Also in the Rogue Valley are many wineries and wine country tours. The Britt Festival, Rogue Valley Symphony, and smaller venues (such as a few of the wineries), provide a wide choice of music performances. br Rafting companies offer their usual adventures (in season) on the Rogue River. Noah's River Adventures is conveniently based out of Ashland. Mountain bikers enjoy the trails that connect from the top of Mt Ashland down to the town (often using Ashland Mtn Adventures bike shuttle service). The surrounding mountains, lakes and rivers provide manifold opportunities for fishing, boating, swimming and exploring. br Seven Pacific Crest trailheads literally surround us. One is a two minute hop, skip and jump from the house. The trailhead for Pilot Rock is a few minutes' drive. Thankfully, not that many people come up to walk or run. On the weekends there may be three cars parked at a trailhead and during the week almost no one. Mt Ashland's alpine forest road and PCT trailheads are accessible snow-free by foot and car from about May through mid-November. br Many opportunities exist for winter sports. For alpine skiers and snowboarders, we have Mt Ashland Ski Area (20 minute drive) and Mt Shasta Ski Park (1.5 hour drive). For x-country skiers and snowshoeing, a multitude of choices which I'm happy to share with you (and the maps you might need). For back-country skiers the areas behind Mt Ashland offer endless ridges and bowls, Mt McLoughlin and Mt Shasta provide interesting terrain as well. And there's good old sledding with your kids from the house and also up on the mountain. We are lift/lodging partners with Mt Ashland Ski Area, so you can purchase lift vouchers from us while you are here. br brDuring all the seasons, our homestead is a good place to find comfort, relaxation, great outdoor exercise and inspiration in the midst of beautiful old forests and meadows and mountains. Whether you are looking for a retreat or a time with family and friends, you can settle in and enjoy. And... kids can play freely and there's plenty of room to roam!brbrThe spacebrThe homestead is located on the Siskiyou Summit just south of Ashland. The 38 acres of forest (unlogged) are the site of the historic old wagon (and early automobile) road, now our driveway, crossing the summit from Oregon to California. This has been our family home since 1982, and we've been caring for this peaceful land ever since. brWe are part of the bird flyway and our forest is home to thousands of birds. Twenty to thirty different bird species can be heard in one sitting on the deck or by the pond. We had a wonderful event last spring when two baby Great Gray owls hatched and the family is still here. Animals are primarily deer, squirrels and fox. brOn the property there are three houses (the Log House, the Forest House, and the Pond House), all far enough away from one another to be private and secluded.brWe live permanently on the property with our dog, Kellen, in the Pond House. We enjoy meeting people and will be available if you need anything during your stay. The Log House will also be rented at times, has a separate driveway and parking area with forest in between. The house has a key pad entrance so you can check in if we're not home when you arrive. The garage door also has a keypad. The central heating and air conditioning is adjustable to your comfort. Many guests like to enjoy a fire in the wood stove on cool evenings. All details for getting to the house, getting into the house, using the WiFi, house rules, and everything else will be available to you upon booking in a detailed itinerary section.brbrGuest accessbrGuests will have access to the Forest House, the seasonal sauna, the gazebo, the pond, and the entire property. EV charger is available on request ($10 per charge).brbrOther things to notebrOur dog, a medium-sized McNab, is very friendly. If you feel uncomfortable around dogs, please let us know and we can adjust to you.brAlso, please note that the sauna is readily available during sauna season (October through mid-May). It is an additional $35 for a sauna. Let us know ahead of time and we will help you get it fired up.
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Bath 2

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Sleep 8

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Exceptional(170)

$418.37

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Private Vacation Home

Hanna`s House | Downtown Retreat, Steps to OSF

Ashland, Oregon, United States

Welcome to Hanna’s House, your cozy downtown Ashland retreat just one block from the Oregon Shakespeare Festival, dining, and shops.br brThis charming bungalow sleeps up to 4 with a queen bed and pull-out sofa. Enjoy a full kitchen, spacious walk-in shower, heated wood floors throughout, and cool AC for year-round comfort. brbrHanna`s House is a quaint, private ADU behind the main house. You`ll have the entire cottage to yourself with a private entrance from the back parking area. There is a small bistro table outside for enjoying your morning coffee or a glass of local wine to end your day.brbrPerfect for a romantic getaway, family trip, or theater weekend in Southern Oregon!brbr*DISCOUNTED OSF TICKETS*brbrWanderLodges is proud to be an OSF Lodging Partner for the Oregon Shakespeare Festival’s 2026 season! As part of this special partnership, all guests with a confirmed reservation at any of our properties will receive an exclusive 20% discount code for OSF tickets in B and C sections—valid for the entire season!brPOLICY REMINDERS:br- Cancelations are dependent on the channel and rate you booked. For direct and standard rates: Cancellations made 5+ days before arrival, a full refund minus a $39 cancellation fee will be issued (non-refundable rates excluded). After that, only the cleaning fee will be refunded.br- Occupancy Limits: Guests agree to not exceed maximum occupancy stated in the listing. $15 per person, per night is charged after the first 3 guests in a reservation. Failure to notify WanderLodges of accurate occupancy may result in additional per person fees if applicable or up to/including reservation termination.br- Parties/Large Gatherings: All parties or occupancy issue creating gatherings are strictly prohibited at all WanderLodges properties, and guests agree to comply with all city, company, and fire code noise and use requirements.br- Pets/Service Animals: Pet friendly properties are subject to an additional $25 per pet/per stay cleaning fee. Pets must never be left unsecured or unattended at the property, and WanderLodges must be notified at time of booking of pet requests. As always, we are happy to accommodate registered service animals of our guests.br- Smoke Free: As a reminder, all WanderLodges properties are smoke and vape free. Smoking indoors, within 10 feet of an entry, or anywhere on the property will incur an additional $250 fee.br- Quite Hours: Considered between 10PM and 8AM. Please keep noise to a minimum in consideration of neighbors. Noncompliance of this will incur a $100 fee per incident, and/or a request to vacate.br- Damages: All damages must be reported to WanderLodges as soon as possible. By booking, guests agree to financial responsibility for all damages due to gross negligence and up to an additional $500 in cleaning fees for negligent use.br***** By booking, guests are agreeing that they are of 21 years of age or older, legally able to agree to these terms, and any minors part of the itinerary will always be accompanied by a parent or guardian. *****
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