Vacation Rentals By Owner In Ashland, OR

Enjoy breakfast with the hummingbirds on the redwood deck surrounded by wisteria and trumpet vines. This bright and cheery duplex cottage has a cozy queen bed, a queen size hide-a-bed in the living room and a fully equipped kitchen. Just a 0.8 mile walk to downtown and the theatres!brbrThere are other cottages (two 3-bedrooms, another 1-bedrooms and a studio) on the property if you are looking for more than one place. Just let us know!brbrNote: Abbott's Cottages is a small family business made up of 9 cottages, all within walking distance to downtown. We have been renting our cottages to tourists in Ashland for 25 years and we usually get 5 star reviews on our other booking platforms. We took a break from renting through VRBO but now we are back- just to explain when you see no reviews! We also have cottages at other locations and soon they will be listed here- in the meantime you can look up Abbott's Cottages to view them all :)

Cottage

ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(3)

$343.79

A beautiful 3 bedroom/2 bath house perfect for families and groups. Quiet, clean and comfortable. Just a 0.7 mile walk to the plaza. brbrThere are other cottages (another 3-bedroom, two 1-bedrooms and a studio) on this property if you are looking for more than one place. Just let us know!brbrNote: Abbott's Cottages is a small family business made up of 9 cottages, all within walking distance to downtown. We have been renting our cottages to tourists in Ashland for 25 years and we usually get 5 star reviews on our other booking platforms. We took a break from renting through VRBO but now we are back- just to explain when you see no reviews! We also have cottages at other locations and soon they will be listed here- in the meantime you can look up Abbott's Cottages to view them all :)

Private Vacation Home

ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown

Ashland, Oregon, United States

Bed

Bath

Sleeps

$331.21

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.

Cottage

Courtside Cottage - WalkScore 93 - Dog Friendly

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(12)

$845.4

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 hang out in our game room with 2 arcades and a ping pong tale. (Pool is open year round but only heated from Memorial Day to Labor Day). 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★GAME ROOM★brLevel up your stay in our newly added game room! Challenge friends and family to ping pong matches, dive into your favorite video games with 2 brand new arcades. Perfect for evenings of entertainment, laughter, and friendly competition.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 Thursday. 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 1 hour and 45 minutes, during which guests will need to exit the pool. Please also note that after chemicals are added, it is not recommended to swim for approximately 24 hours to ensure proper water balance and safety.br- Garden maintenance occurs on Wednesdays. 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.brbrEarly Check-In / Late Check-Out Options:br - We may be able to accommodate an early check-in starting at 1:30 PM or a late check-out until 1:30 PM for an additional fee of $150.00, subject to availability and scheduling.br - To help us coordinate with our cleaning and operations teams, requests must be made at least 1 day in advance and are not guaranteed until confirmed by management.br - For guests needing significantly earlier arrivals or later departures, we recommend booking the previous or following night to ensure uninterrupted access to the property.br - Unapproved late checkouts will incur an additional charge of $300.

Private Vacation Home

The Ashland Social | Entire Estate

Ashland, Oregon, United States

Bed

Bath

Sleeps

$1078.39

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.

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

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(2)

$199.47

Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtown Ashland! Welcome to your PREMIUM Hyatt Prairie Cabin. The primary bedroom has a queen bed, and the sleeping loft has two twin beds. Full kitchen, dining room and bathroom. The cabin has premium furnishings, BBQ, deck, (electric) fireplace, Smart TV, DVD player, satellite TV and WiFi.

2 bedroom cabin, huge deck, lodge-style furnishings.

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(2)

$199.52

Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtown Ashland! Welcome to your PREMIUM Hyatt Prairie Cabin. The primary bedroom has a queen bed, and the sleeping loft has a full and a queen bed. Full kitchen, dining room and bathroom. (electric) fireplace, Smart TV, DVD player, satellite TV and WiFi. Large deck with BBQ. .

2 bedroom cabin plus loft, huge deck, lodge-style furnishings.

Ashland, Oregon, United States

Bed

Bath

Sleeps

$397.82

Hyatt Prairie Cabin Compound! Two cabins connected by a common deck. Two full kitchen, dining rooms, and two bathrooms. Two primary bedrooms (queen beds) and two 56″ tall sleeping lofts (one full bed and three twins). Two BBQ’s, huge deck, (electric) fireplace, ‘smart’ TV, DVD player, satellite TV, and Wi-Fi. .

2 cabins with 4 bedrooms, hot tubs, dining room and full kitchen.

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(10)

$375.06

Gaze out on the twinkling lights of the Ashland hills from this new luxury condo in the heart of downtown, just steps from culinary delights and boutique shopping and a short walk to Oregon Shakespeare Festival venues. Boasting a spacious great room with state-of-the-art fireplace and balcony, a luxurious king bedroom with an oversized bathroom, fully appointed modern kitchen and covered parking just steps from the secured foyer with elevator to 2nd floor. Adjacent to fast charging EV stations.

Luxury condo with king bedroom, two bathrooms, full kitchen.

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(1)

$1205.56

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.

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

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(8)

$464.14

Welcome to Ashland's new luxury vacation destination located in the heart of downtown, just steps to the culinary delights, boutique shops and a short walk to Oregon Shakespeare Festival venues. The Plaza North Suites set a new standard of architectural and design excellence in Ashland. The Alexander Suite features 2 bedrooms, one king and one queen, two full baths, a fully appointed modern kitchen, two balconies, state of the art fireplace and gorgeous mountain views.

Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(4)

$415.96

About this space One block from OSF. Enjoy a relaxing getaway at the Pioneer House. originally built in 1904. Up to six guests. Easy access to dining, wine tasting, and shopping. Off street parking is also available This spacious two bedroom historic home is fully renovated. Both bedrooms have a king size bed. There is a queen-size sectional sofa in the living room as well. The bathroom includes a clawfoot tub and shower. Large kitchennette, a smart TV with DVR, washer/dryer, and lovely views from the mini-deck

Spacious 2 bedroom historic home with two king beds and kitchenette.

Ashland, Oregon, United States

Bed

Bath

Sleeps

$470.83

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

Bed

Bath

Sleeps

Exceptional(2)

$199.52

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

Bed

Bath

Sleeps

Exceptional(1)

$1315.89

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

Bed

Bath

Sleeps

Exceptional(4)

$945.59

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

Bed

Bath

Sleeps

Exceptional(14)

$504.28

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

Bed

Bath

Sleeps

Exceptional(13)

$348.3

Plaza North is a luxury vacation destination located in the heart of downtown Ashland, just steps to the culinary delights, boutique shops and a short walk to Oregon Shakespeare Festival. The Plaza North Suites set a new standard of architectural and design excellence. The Sonoma Suite features 1 bedroom with a king bed, a spacious full bath and fully appointed modern kitchen, state-o-the-art fireplace and large window with view. Covered parking steps from secured foyer and elevator.

Luxury condo with king bedroom, two bathrooms, full kitchen.

Ashland, Oregon, United States

Bed

Bath

Sleeps

Exceptional(1)

$994.76