Vacation Rentals By Owner In Ashland, OR

The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyou Mt. range beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from the downtown center plaza with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Ashland, Oregon, United States

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$105.65

Experience Ashland like a local in this 3-bedroom flat/loft/apartment. Built in the late1800s, this bright & tranquil space showcases modernized beauty and stylish updates, while preserving its charm and history. Enjoy organic green gardens, easy downtown walking, and the simple elegance this space has to offer. brOur neighborhood spot is very quiet and peaceful with pure convenience. The loft is an eco-friendly and all natural home.The bedrooms feature a king, queen, and full bed, ensuring a comfortable stay for guests. The full bathroom is charming with a full bath/shower option and a complete set of washer and dryer machines in the unit. Enjoy a chef's kitchen with full updates and new appliances. Whether you're relaxing in the living room or exploring the city, this serene space is a ideal for a monthly getaway and/or perfect for a traveling professional, working from-home, or a winter seasonal stay. We hope you enjoy what our place and Ashland has to offer.

Farmhouse Light-filled Loft in Ashland's Historic Railroad District

Ashland, Oregon, United States

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$369.07

Located just blocks away from the OSF theaters downtown, Courtside Cottage is the perfect place to land on your next visit to Ashland. Park your car and live like a local in the heart of town. You’ll feel right at home with just a two-minute walk to restaurants and boutique shops. The cottage is accessible from an alley on a very quiet residential street and has been fully remodeled with a cozy but modern aesthetic.

Courtside Cottage - WalkScore 93 - Dog Friendly

Ashland, Oregon, United States

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$188.63

Quaint Cottage. Amazing location 1.5 blocks to Downtown Ashland. Outdoors Private courtyard enclosed with fence in front of Cottage, with outdoor seating and dining for two. Full kitchen w new Stainless stove. Pets may be welcome subject to written owner approval. Additional deposit applies.brFormerly known as the Loft.

Sage Ashland Cottage

Ashland, Oregon, United States

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Bath

Sleeps

$733.32

Welcome to our luxurious and tranquil retreat, featuring two stunning master bedrooms. One bedroom boasts a jetted tub in its en suite bathroom, while the other features French doors leading out to the pool area.brbr★HOME OVERVIEW★brWelcome to our large, luxurious and tranquil retreat, featuring two stunning master bedrooms. All four bedrooms have king sized beds and en suite bathrooms making it the perfect friends and family getaway! brbr★SLEEPING ACCOMMODATIONS★brbrWe can sleep 12 people total! brbrBedroom 1: King Bed, ensuite bathroom with jetted tub, 55 tvbrBedroom 2: King Bed + Queen fold out couch, ensuite bathroom with french doors that open to the pool area, 55 tvbrBedroom 3: King Bed, ensuite bathroom, 55 tvbrBedroom 4: King Bed, french doors to the backyard, small tvbrLiving Room: Queen fold out couchbrbrThe spacious living room, dining room, and kitchen provide ample space for enjoying time with friends and family.brbr★FIVE STAR AMENITIES★brStep outside to our inviting outdoor area, complete with a large table and chairs, a bistro table, a barbecue, a heat lamp, and plenty of comfortable seating. Relax in our hot tub or seasonal pool with loungers, or take advantage of our 2-person sauna in the garage.brbr★LIVING AREA★brRelax on our large (111 by 111) sectional sleeper sofa and stream your favorite shows on our Smart TV (Roku) or just enjoy the fireplace that turns on with a flick of a switch. Enjoy access to Netflix, Hulu, Prime Video, and Apple TV by simply entering your password. br‎br★KITCHEN★brThe kitchen is a chef's dream. You'll be amazed at how well stocked this fully loaded kitchen is whether you want to prepare a simple breakfast or spend the day cooking a feast. From every size pot and pan to even some rare spices this kitchen is perfect for your friend and family getaway. Our coffee and tea bar has everything you need to get going in the morning. Enjoy a 2-in-1 coffee maker with both Keurig and drip options. There is also a kitchenette in the 4 (yellow) bedroom, which is the adjacent studio so you can have a cup of coffee before joining the rest of the group. brbr★DINING★brYou've got options! The formal dining room has a large table that seats 6 comfortably (or squeeze 8 in!). The breakfast nook seats 4 and kitchen island seats 2. On our better weather days you can enjoy a large outdoor table for 6 or a small bistro table for 2. The 4th bedroom (studio unit) has a small table for 2. br‎br★BATHROOMS★brThere are 4.5 bathrooms total. Each bedroom has an ensuite and there is a half bath off the living room. There are 2 bathtubs (one large jetted tub in the master bedroom and the second one in the other upstairs bedroom). Towels, shampoo, conditioner and body wash are provided.brbr★LAUNDRY ROOM★brThere is a full sized washer and dryer in the laundry room upstairs.brbr★PARKING★brThere is one spot in front driveway for your car and ample street parking.brbr★RESTAURANTS & BARS★brThe best of the best on the Ashland Plaza is a 4 minute drive away!brbr★HEATING & AC★brThe house has a central heat and AC with 2 thermostats (one on each floor). The 4th adjacent bedroom has a window AC unit, wall heat as well as heated floors. brbrFor safety, there is a ring doorbell at the front door. It is active 24/7. Video and sound recording is motion activated. The home is also equipped with a decibel monitoring sensor located inside and outside of the home. It is 100% privacy compliant and is required on this property. Tampering with or disabling the ring doorbell and noise monitoring sensor will immediately cancel the reservation.brbrExperience the ultimate in luxury and relaxation at our retreat – book your stay todaybrbrIMPORTANT REMINDERS:br- You will be asked to sign a rental agreement.br- Pool maintenance is scheduled every Monday. During this time, our dedicated team will be working diligently to ensure the pool is in top-notch condition for your safety and enjoyment. The maintenance process typically takes approximately an hour and 45 minutes to complete and will need guests to exit the pool during that time.br- Garden maintenance occurs on Fridays. Our team ensures the garden remains in excellent condition for your enjoyment.brbrCancellation Policy: 50% refund up until 60 days prior to arrival. No refund if cancelled within 60 days.brbrUnapproved late checkouts will incur an additional charge of $300.

Retreat in Style: 4BR Jewel, Pool, HotTub

Ashland, Oregon, United States

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Select Dates for Price

A private slice of paradise awaits at this cozy Ashland vacation rental! Hosting a fenced patio and yard, vegetable garden, full kitchen, bath, and an unbeatable downtown location, this lovely cottage ensures a comfortable stay with all the amenities of home in a studio living space. Walk downtown to explore the shops, restaurants, and cultural activity, or rent bicycles for a spin on the Central Bike Path. Additionally, you’ll be surrounded by mountain vistas and several unique wineries!brbr-- THE PROPERTY --brbrWalk Downtown | Full Kitchen | FireplacebrbrPerfect for the romantic couple, efficient business traveler, wine buff, and outdoor enthusiast, 'Nancy's Garden - The Loft,' an ideally located Ashland cottage, offers a peaceful, modern getaway just blocks from countless attractions.brbrCottage: Queen BedbrbrOUTDOOR LIVING: Fenced garden/patio, fire pit, herb garden, seating, outdoor shower, steps to shops/restaurants & more, electric bicycle rentals a half-block away by the Safeway brINDOOR LIVING: Flat-screen Smart TV, fireplace, desk, walk-in shower w/ grab rails brKITCHEN: Well equipped, stainless steel refrigerator, tile countertop, coffee maker, coffee grinderbrGENERAL: Free WiFi, air conditioning, central heating, iron & board, linens, towels brPARKING: Assigned parking adjacent to the cottagebrbr-- THE LOCATION --brbrOUTDOOR ACTIVITY: North Mountain Park (1.0 miles), Hunter Park (1.3 miles), Lithia Park (1.7 miles), Acid Castle Rocks (1.9 miles), Hald/Strawberry Park (2.1 miles), Siskiyou Mountain Park (2.9 miles), Oak Knoll Golf Course (3.5 miles), Emigrant Lake (7.2 miles), Mt Ashland Ski Area (20.2 miles), Cascade-Siskiyou National Monument (23.9 miles) brDOWNTOWN ASHLAND (walking distance): Smithfields Restaurant, Alchemy Restaurant and Bar, Pangea, Pie + Vine, The Growler Guys, Zoey’s Cafe & All Natural Ice Cream, Pony Espresso Coffee House & Cafe, Standing Stone Brewing Company, Martolli’s Hand Tossed Pizza Plaza, Greenleaf, Oberon’s Restaurant & Bar, Louie’s of Ashland, Brickroom, Oregon Shakespeare Festival, Angus Bowmer Theatre, Thomas Theatre, Varsity Theatre, Escape Ashland, Historic Ashland Armory, Oregon Cabaret Theatre, Ashland Art CenterbrFAMILY FRIENDLY: Southern Oregon University (0.4 miles), Ashland Street Cinema (1.1 miles), ScienceWorks Hands-on Museum (1.0 miles), Central Bike Path (1.0 miles), Talent (6.1 miles), Medford (17.3 miles)brWINERIES: Weisinger Family Winery (2.9 miles), Irvine & Roberts Vineyards (4.9 miles), Belle Fiore Winery (4.9 miles), Grizzly Peak Winery (3.4 miles), Dana Campbell Vineyards (2.1 miles), Simple Machine (5.1 miles), Paschal Winery (6.9 miles), Pebblestone Cellars (8.6 miles), EdenVale Winery (11.1 miles), 2Hawk Vineyard & Winery (13.5 miles), RoxyAnn Winery (16.4 miles)brAIRPORT: Rogue Valley International-Medford Airport (16.4 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Dogs allowed with a $75 per stay fee + fees and taxes (1 max)br- No events, parties or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Warm & Inviting Ashland Cottage < Half-Mile to SOU

Ashland, Oregon, United States

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Exceptional(20)

$795.09

Our family ranch home is nestled at the base of Grizzly Peak, with expansive views of Mt Ashland, and the Rogue Valley. Enjoy our large, in-ground pool, or warm up in our hot tub. Our pond has a pergola, with a swing, perfect for contemplating the gorgeous views of the surrounding mountains. The house is located on the Ashland Lavender Estate, which is transitioning from a hay farm, to an olive, and lavender farm. With our organic raised vegetable garden, mature fruit trees, and local blackberries, you will be able to enjoy all that southern Oregon has to offer. A large, chefs kitchen, and formal dining room, are perfect for cooking all the goodies you can pick up at the farmers markets. The expansive living room has a wood burning fireplace, and views of downtown Ashland. The master bedroom has a bathroom en-suite, and a 2,000 lb, basalt bathtub, and it’s own fireplace. The fireplace in the master suite can be enjoyed from the bedroom or the ! Perfect spot to enjoy a tranquil soak and the view of Mt Ashland. The spacious arrangement of the home allows for privacy inside and out. There is a fire pit on the promenade, with Adirondack chairs for sitting. A nice spot to sip local wines and watch the sunset. This home has views in all directions! We have a bocce ball court, fun for the whole family. There is a basketball boo, and ping pong table for fun and games. A pergola, at the top of the pond is a great spot for morning yoga. We are close to downtown, the Oregon Shakespeare Festival, and award winning restaurants. Hike our mountains, or enjoy the new Japanese garden in Lithia park. The adventurous might like the incredible mountain bike trails above Lithia Park. Fun for all! brbrWelcome to our charming farm house vacation rental in Ashland, Oregon! Situated amidst lush orchards and boasting stunning views of the valley and mountains, this is the perfect place to relax and unwind in the serene countryside.brbrOur farmhouse features four comfortable bedrooms that can accommodate up to eight guests, making it the ideal getaway for families or groups of friends. There are three bathrooms in the house, so everyone will have plenty of space to get ready in the morning.brbrThe living room is cozy and inviting, with comfortable seating and a fireplace that's perfect for chilly evenings. The dining room is adjacent to the living room and features a large table that can comfortably seat eight, making it a great space for meals or game nights.brbrThe gourmet kitchen is fully equipped with everything you need to cook up delicious meals, including high-end appliances, cookware, and utensils. You'll also find a coffee maker, toaster, and blender, as well as plenty of pantry staples to help you get started.brbrOne of the standout features of our farm house is the outdoor space. There's a swimming pool where you can cool off on hot days, as well as a hot tub where you can relax and unwind after a long day of exploring. You can also play bocce ball on the court, or challenge your friends to a game of ping pong.brbrThere's a pond with a waterfall that creates a tranquil atmosphere, and a fire pit where you can gather around and roast marshmallows under the stars. With views of the valley and mountains all around, you'll never tire of the scenery.brbrCome stay with us at our farm house vacation rental in Ashland, Oregon, and experience the beauty and serenity of the countryside! This home can be reserved for functions and parties there is an extra fee please inquire if interested.

Agritourism

Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Ashland, Oregon, United States

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Bath

Sleeps

$143.84

About this spacebrVictorian home built in 1895, walk to downtown shops, restaurants, Oregon Shakespeare Fest. and Lithia Park. Private suite w/ sunroom, bedroom, bathroom and private entrance. Eco-friendly, hypoallergenic operation.br30 min to Mt. A. Ski area, 10 min to hiking and mountain biking. 5 min. to Jackson Wellsprings.brDOG FRIENDLY, small fenced front yard, 1 mile to dog park. Walkable to downtownbrPLEASE LET US KNOW YOU HAVE A PET; $25 for 1, $35 for 2 pet feebrPermit#:17-795brThe spacebrQueen size bed with pillow top, and pull-out couch in sunroom. Shower and bathtub. Coffee and tea. Hot and cold filtered water. Mini fridge. Coffee maker. Wine glasses. 37” Flatscreen TV with Netflix. Complimentary Wi-Fi. Energy efficient heating and AC unit. Full-length mirror. Armoire with hangers. Room darkening curtains. Sleep easy sound machine.brbr*Cleaned with natural productsbrGuest accessbrGround floor private entrancebrFree private parking spacesbrShared patio area with forested landscapingbrOther things to notebrSuite is connected to main home, but still completely private. We are respectful and quiet hosts, although you might hear us on occasion.brbrSuite accommodates 3 sleepers.brbrPlease do not leave pets unattended

Jazzy B Suite~Historic, eco/dog friendly

Ashland, Oregon, United States

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$457.15

Historic home - One block from OSF. Easy access to dining, wine tasting, and shopping. Originally built in 1904, this home is fully renovated and hosts up to guests. Three bedrooms include a king and two queen size beds. A sofa bed is in the common area as well. There are two bathrooms, a kitchenette and a convection microwave. Also includes a smart TV with DVR, washer/dryer, and french doors that open onto a covered porch and fenced front yard. Private, off street parking also available.

3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.

Ashland, Oregon, United States

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Sleeps

$835.14

About this space This spacious five bedroom historic home has been fully renovated, has brand new furnishings, and is perfect for up to fourteen guests. Five private bedrooms include three king and two queen size beds, there are also sofa beds in the common areas. There are three full bathrooms. Two well-appointed kitchenettes. An induction cooktop for all of your stovetop cooking needs and a convection microwave. Includes a smart TV, washer/dryer, and doors that open onto a covered porch and fenced front yard.

5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.

Ashland, Oregon, United States

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$433.74

About this space This two-story, modern home has three bedrooms. The primary bedroom has a king-sized bed and the guest rooms each have queen-sized beds. A spacious living room includes a comfortable sofa bed that sleeps two, making this home the perfect location for up to 8 guests. Has a modern, fully appointed kitchen as well as an upper balcony and lower patio. The home has two full bathrooms with shower stall downstairs and jetted tub upstairs. Also includes a smart TV with DVR and washer/dryer.

2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.

Ashland, Oregon, United States

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Bath

Sleeps

$204.37

About this space Welcome to your Hyatt Prairie Cabin with views and a two person Hot Tub! The primary bedroom, located in the 56″ tall sleeping loft, has a queen size bed, the downstairs bedroom has a queen size bed and 43″ Smart TV and the living room has a queen sleeper sofa with a 55″ Smart TV (plus surround sound soundbar). Full kitchen, dining room, and bathroom. The cabin has a two person Hot Tub, BBQ, hammock, deck, (electric) wood stove, ‘smart’ TV, DVD player, satellite TV, and Wi-Fi.

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Ashland, Oregon, United States

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Sleeps

$1113.9

About this space The house has five bedrooms, each with its own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace, flat screen television and plenty of seating. The house has a large patio. The Cottage has a separate entrance and is one bedroom and one bath and has a futon in the living room to accommodate two additional guests. there is a kitchen with a microwave, refrigerator and range. There is a large private parking area that can accommodate up to four cars.

2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area.

Ashland, Oregon, United States

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Bath

Sleeps

Exceptional(3)

$238.02

The Bluemoon Cottage is a perfect getaway for a couple or friends visiting Ashland, OR. The one bedroom (queen bed), one bathroom cottage has a futon in the living room to accommodate two additional guests. There is a full kitchen with a microvave, refridgerator, and range. The back patio has outdoor seating to enjoy a cup of coffee in the morning or relax at the end of the day with a glass of your favorite local wine.

1 bedroom, 1 bathroom cottage with sleeper sofa & full kitchen.

Ashland, Oregon, United States

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Sleeps

$1166.85

What this place offers : 8 Bedrooms, 5 bathrooms, laundry , Washing machine , Entertainment , TV , Heating and cooling , Air conditioning , Internet and office , Wifi , Dedicated workspace , Kitchen and dining , Kitchen , Space where guests can cook their own meals. This vacation home is located in Historic Downtown District, a neighborhood in Ashland. Paschal Winery and StoneRiver Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore North Mountain Park and Lithia Park.

Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.

Ashland, Oregon, United States

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Bath

Sleeps

Exceptional(3)

$723.64

About this space The Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, dining room with seating for 12, a living room with a library, washer and dryer, front porch and ample outdoor seating surrounded by garden. Downstairs there are three king bedrooms, and one queen bedroom, each with its own bathroom. There is a sitting room as well! Upstairs there are three more queen bedrooms each with its own bathroom!

Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.

Ashland, Oregon, United States

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Bath

Sleeps

$900.51

Ashland's premier luxury destination located in the heart of downtown, the Penthouse encompasses the entire 3rd floor, boasting 360° views, features a year-round lanai with gourmet outdoor kitchen. Inside the beautiful living and kitchen area is designed as the ultimate gathering space with deluxe amenities. Two large bedrooms with king beds, an ensuite bathroom with heated floors, a second full bath plus large den/office and 1/2 bath. Covered parking, secured foyer, adjacent charging stations.

Lodge

2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms

Ashland, Oregon, United States

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Bath

Sleeps

$1169.64

With Suites Trinity, you and your guests will enjoy the entire second floor of Plaza North. Consisting of three separate suites each with its own fully appointed modern kitchen, state-of-the-art fireplace, high ceilings, bright spaces, and large picture windows with gorgeous mountain views. 4 bedrooms, 6 bathrooms and 3 sofa sleepers. Plus covered parking just steps from secured foyer with elevator to the 2nd floor with adjacent fast charging stations.

Lodge

Entire 2nd floor of Plaza North with 3 separate suites each with its own kitchen and bedrooms.

Ashland, Oregon, United States

Bed

Bath

Sleeps

$210.74