Ashland Rentals
From $310 per night (USD)VRBO
Stacy's 2nd St Cottage. Steps to downtown.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
1200 sq ft downstairs cottage located in the historic railroad district 1/2 block to downtown and a five minute walk to ...
From $310 per night (USD)VRBO
From $283 per night (USD)VRBO
Light-Bright-Stylish! Sparkling Clean! 15-min level walk to town. Private deck.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Nursery Street Guesthouse has always received 100% 5-star ratings for cleanliness, location, and hosting. Come relax i ...
From $283 per night (USD)VRBO
From $328 per night (USD)VRBO
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
3 bedroom, 2 bath villa on acreage within minutes of theaters, restaurants and shopping. Very private with modern kitche ...
From $328 per night (USD)VRBO
From $223 per night (USD)VRBO
High Street Cottage Artists' Garden Cottage Clean & Beautiful
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Set in one of Ashland's oldest and most desired neighborhoods. This 1931 cottage has been lovingly restored back to its ...
From $223 per night (USD)VRBO
From $521 per night (USD)VRBO
Asian Inspired Escape with View - Just 3 Miles from Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Asian meets Craftsman in this two story hillside home perched high above the city lights. Full kitchen with every ameni ...
From $521 per night (USD)VRBO
From $218 per night (USD)VRBO
The Terra Cottage Inn - Ashland, Oregon
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestle into one of Ashland's best neighborhoods, a beautiful, short 4 block walk to world class theatre, dining, arts an ...
From $218 per night (USD)VRBO
From $284 per night (USD)VRBO
232-Duplex-Private Bathroom-Mountain View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
232 4th St is a 3 bedroom 2 bathroom home. There are 2 full size beds and a queen bed. The home features a fully stocked ...
From $284 per night (USD)VRBO
From $338 per night (USD)Expedia
230-Downstairs-Duplex-Private Bathroom-Mountain View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great three bedroom - two bath accommodation in historic, downtown location Welcome to “The Garden" at the 4Th Street In ...
From $338 per night (USD)Expedia
From $293 per night (USD)VRBO
Ashland's Mountain View Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Mountain View Cottage Ashland’s newest vacation rental The perfect place to stay for your next Ashland get a ...
From $293 per night (USD)VRBO
From $102 per night (USD)VRBO
Vacation Home in Beautiful Ashland (Ashland, OR)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming, remodeled, furnished Victorian-Style, spacious home, only 4 easy blocks from downtown Ashland, the Plaza, Worl ...
From $102 per night (USD)VRBO
From $156 per night (USD)VRBO
Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charmi ...
From $156 per night (USD)VRBO
From $146 per night (USD)VRBO
East Main Ease!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly remodeled townhome is private, but just a short walk to downtown Ashland. Coffee shop, restaurants, bike trails a ...
From $146 per night (USD)VRBO
From $118 per night (USD)VRBO
Ashland, Oregon. Available for two months : July and August!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our cottage is very private and quiet, yet we are only a few minutes walk from the Festival, downtown and our 73 acre Li ...
From $118 per night (USD)VRBO
Click For PricingVRBO
Ashland Townhouse, furnished
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, 2 and 1/2 bath furnished townhouse located 1/2 mile from grocery shopping and the YMCA, 1 mile from Southern ...
Click For PricingVRBO
From $257 per night (USD)VRBO
Charming Space Next to Everything, Walk Anywhere!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Park the car the duration of your stay and feel at home in quaint little Ashland town. Spacious and artistic decor is pe ...
From $257 per night (USD)VRBO
From $368 per night (USD)VRBO
Charming Two Bedroom Private Cottage within walking distance to Ashland downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Abigail's Private Two Bedroom Self- Catering Vacation Cottage is within walking distance to the town plaza, Theatre and ...
From $368 per night (USD)VRBO
From $474 per night (USD)VRBO
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BLUE HYACINTH Welcome to the Blue Hyacinth, a lovely 3 BDRM-2 BATH house, at Blossom View Cottages. We are located in ...
From $474 per night (USD)VRBO
From $387 per night (USD)Expedia
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half ...
From $387 per night (USD)Expedia
From $286 per night (USD)VRBO
Home Sweet Home - Relax w/ Beautiful Big Yard and Steam Shower
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summer Rental Home in beautiful Ashland Oregon. We are renting out our home for July 26 - August 24, 2018. Minimum Ren ...
From $286 per night (USD)VRBO
From $158 per night (USD)Expedia
The Maple Apartment at Tudor House Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Upstairs one bedroom has a queen sized bed, the other has two twin beds, with a full bathroom. Downstairs another full b ...
From $158 per night (USD)Expedia
From $156 per night (USD)VRBO
The Dogwood Suite at Tudor House Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
The upstairs Bedroom has a queen and a twin bed. The downstairs has a full kitchen, dining table, sofa-bed, and TV. Fr ...
From $156 per night (USD)VRBO
From $176 per night (USD)VRBO
Downtown Ashland private cottage with garden patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Silver Frog Guesthouse, complete with a queen bed, fold-out twin couch, kitchen and shower-only bathroom, is set bac ...
From $176 per night (USD)VRBO
From $222 per night (USD)VRBO
Custom Ashland Home with Fantastic Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet ...
From $222 per night (USD)VRBO
From $144 per night (USD)Expedia
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly remodeled, modern guest suite is nestled in the Tolman Creek canyon and surrounded by a beautiful madrone, pi ...
From $144 per night (USD)Expedia
From $147 per night (USD)VRBO
Exquisite Artist's home, all summer or month to month.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
This home is beautifully appointed with high end furniture, oriental rugs and art from across the globe. It has the best ...
From $147 per night (USD)VRBO
From $331 per night (USD)Expedia
Quiet and peaceful cottage close to downtown
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Come retreat in our oasis during your stay in Ashland! Charming 1 bedroom, 2 bathroom home, tucked away from the busy b ...
From $331 per night (USD)Expedia
Click For PricingVRBO
In the historic railroad district, walking distance to all the best of Ashland!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
COVID-19 PANDEMIC - please call direct for information on cleaning protocols and further information on cancelation poli ...
Click For PricingVRBO
From $160 per night (USD)VRBO
Monthly rental offering privacy and views near Ashland Plaza.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A well appointed, executive home offering privacy and grand views in a fantastic Ashland Location. Natural lighting abou ...
From $160 per night (USD)VRBO
From $138 per night (USD)VRBO
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in ...
From $138 per night (USD)VRBO
From $124 per night (USD)Expedia
Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Arrive. Park your car. Exhale & walk for the remainder of your visit. You are now adjacent to 93- acre Lithia Park and d ...
From $124 per night (USD)Expedia
From $98 per night (USD)VRBO
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Arrive. Park your car. Exhale & walk for the remainder of your visit. You are now adjacent to 93- acre Lithia Park and ...
From $98 per night (USD)VRBO
From $78 per night (USD)Expedia
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You have arrived and are now adjacent to 93- acre Lithia Park and downtown Ashland. Within a 5-minute walk, you will dis ...
From $78 per night (USD)Expedia
From $122 per night (USD)VRBO
3 Bedroom Home with hot tub - Walking distance to everything - Quiet street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This fully furnished 3 bedroom home has the benefits of a great location: 20 minute walk to downtown, 5 minute walk to ...
From $122 per night (USD)VRBO
From $216 per night (USD)Expedia
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in ...
From $216 per night (USD)Expedia
From $307 per night (USD)VRBO
Premier Downstairs Flat in Perfect Down Town Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a beautiful new 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There is a laund ...
From $307 per night (USD)VRBO
From $106 per night (USD)Expedia
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and upd ...
From $106 per night (USD)Expedia
From $354 per night (USD)VRBO
Indulgent Retreat: 3 King Suites, Pool & Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Luxury 3BR escape with pool, and sauna awaits near the Oregon Shakespeare Festival. Indulge in refined living with 3 kin ...
From $354 per night (USD)VRBO
From $669 per night (USD)Expedia
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our family ranch home is nestled at the base of Grizzly Peak, with expansive views of Mt Ashland, and the Rogue Valley. ...
From $669 per night (USD)Expedia
From $261 per night (USD)VRBO
New Downtown 3 Bedroom Upstairs Flat with views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This is a beautiful new upstairs 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There i ...
From $261 per night (USD)VRBO
From $395 per night (USD)VRBO
Helman Street Penthouse with a View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This award winning building is located in Ashland's Historic railroad district just 3 blocks to Ashland's Plaza. A light ...
From $395 per night (USD)VRBO
From $468 per night (USD)VRBO
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This luxury vacation rental is uniquely designed for elegance and comfort that will make you feel right at home. The new ...
From $468 per night (USD)VRBO
From $371 per night (USD)VRBO
The Perfect Vacation Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Central Avenue Cottages is licensed by the city of Ashland and is a charming turn of the Century house that has been tas ...
From $371 per night (USD)VRBO
From $414 per night (USD)VRBO
Railroad District, steps to downtown, everything you need to enjoy Ashland!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Garden Suite at Second Street Cottages! (Permit#:06-01959) The Garden Suite is located just two blocks fr ...
From $414 per night (USD)VRBO
From $314 per night (USD)Expedia
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Step into a piece of Ashland history at the Ohana House, a charming 1905 3-bedroom, 2-bath home just a 2 minute walk fro ...
From $314 per night (USD)Expedia
From $124 per night (USD)VRBO
Cozy Ashland Studio: King Bed, 1 mile from Plaza!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our newly built studio cottage, the ultimate haven for solo travelers exploring the beautiful city of Ashland ...
From $124 per night (USD)VRBO
From $175 per night (USD)Expedia
Courtside Cottage - WalkScore 93 - Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located just blocks away from the OSF theaters downtown, Courtside Cottage is the perfect place to land on your next vis ...
From $175 per night (USD)Expedia
From $780 per night (USD)VRBO
Ashland Luxury: 4 King suites, pool & hot tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to our luxurious and tranquil retreat, featuring two stunning master bedrooms. One bedroom boasts a jetted tub i ...
From $780 per night (USD)VRBO
From $186 per night (USD)Expedia
Sage Ashland Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Quaint Cottage. Amazing location 1.5 blocks to Downtown Ashland. Outdoors Private courtyard enclosed with fence in front ...
From $186 per night (USD)Expedia
From $277 per night (USD)VRBO
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Guest Room 1, the perfect getaway for two! With a plush queen size bed, luxurious walk-in dual head shower, a ...
From $277 per night (USD)VRBO
From $306 per night (USD)Expedia
The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our most luxurious and romantic suite. Featuring a full private bathroom with the famous “twin tubs” that are ...
From $306 per night (USD)Expedia
From $281 per night (USD)VRBO
The Peerless Hotel | Junior Suite #2 | Jetted Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Junior Suite #2 is a cozy, unique, one-of-a-kind space with a queen bed, a private bathroom, and a jacuzzi tub. Relax in ...
From $281 per night (USD)VRBO
From $298 per night (USD)Expedia
The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the second floor, this spacious and bright suite features wrap around windows, a 4-post luxurious queen bed, ...
From $298 per night (USD)Expedia
From $280 per night (USD)VRBO
The Peerless Hotel | Junior Suite #5 | Jetted Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into a world of elegance and romance in this French-inspired guest room on the second floor. You’ll feel pampered b ...
From $280 per night (USD)VRBO
From $266 per night (USD)Expedia
The Peerless Hotel | Signature Room #6 | Clawfoot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the second floor, our most petite yet whimsical guest room features exposed brickwork, a clawfoot tub for soa ...
From $266 per night (USD)Expedia
From $356 per night (USD)VRBO
Mountain Ave House by WanderLodges
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this beautifully renovated turn of the century 3 bed/ 2 bath house in Ashland, OR. Featuring one king bed on ...
From $356 per night (USD)VRBO
From $179 per night (USD)Expedia
Peaceful, spacious home on 8 acres. Pet-friendly, close to town, and a creek!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
You will be an easy 10 minute drive from Downtown Ashland and feel like you are out in the country. The home is 1200 squ ...
From $179 per night (USD)Expedia
From $328 per night (USD)VRBO
Artsy Downtown Historical House: Steps to Shakespeare
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: **Welcome to The Matriarch Heritage House** Located in the HEART of Ashland. Park your car and walk to all you' ...
From $328 per night (USD)VRBO
From $420 per night (USD)Expedia
Swank House on Main St in Ashland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Dip into an Ashland vacation experience unlike any other. Stroll to your morning coffee or evening theater show ...
From $420 per night (USD)Expedia
From $223 per night (USD)VRBO
A Cowslip's Belle Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>While you're here, you can enjoy all the comforts of home and more, including free WiFi and a coffee/tea maker, as we ...
From $223 per night (USD)VRBO
From $721 per night (USD)Expedia
Modern Farmhouse on Emigrant Creek. Peaceful, views, and a dance studio!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy peace indoors and out in this spacious, stunning and serene home. It was built by a renowned local contractor in 2 ...
From $721 per night (USD)Expedia
From $147 per night (USD)VRBO
Downtown Ashland Studio - 3 blocks from the plaza!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival—boutique shops, award winning w ...
From $147 per night (USD)VRBO
From $339 per night (USD)Expedia
House + 2 Studios- 3 blocks from the Plaza!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Helman House and Cottages ~ Old Ashland Charm, Short Walk to the Plaza ★HOME OVERVIEW★ One and a half blocks away from ...
From $339 per night (USD)Expedia
From $129 per night (USD)VRBO
Quaint Downtown Ashland Studio- pet friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival—boutique shops, award winning w ...
From $129 per night (USD)VRBO
From $768 per night (USD)Expedia
Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Oregon Shakespeare Festival Lodging Partner! Book with us for a 20% discount on select seats throughout the season. A F ...
From $768 per night (USD)Expedia
From $219 per night (USD)VRBO
Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Oregon Shakespeare Festival Lodging Partner! Book with us for a 20% discount on select seats throughout the season. - F ...
From $219 per night (USD)VRBO
From $207 per night (USD)Expedia
Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Oregon Shakespeare Festival Lodging Partner! Book with us for a 20% discount on select seats throughout the season. Cha ...
From $207 per night (USD)Expedia
From $255 per night (USD)VRBO
Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
**Oregon Shakespeare Festival Lodging Partner! Book with us for a 20% discount on select seats throughout the season.** ...
From $255 per night (USD)VRBO
From $307 per night (USD)Expedia
2 bedroom cabin, huge deck, lodge-style furnishings.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtow ...
From $307 per night (USD)Expedia
From $218 per night (USD)VRBO
Barclay Klum House by WanderLodges | Soaking Tub | Gourmet Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Introducing the Barclay-Klum House: A meticulously restored 2-bedroom, 1-bath gem, walking distance to Ashland's vibrant ...
From $218 per night (USD)VRBO
From $204 per night (USD)Expedia
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Welcome to your Hyatt Prairie Cabin with views and a two person Hot Tub! The primary bedroom, located ...
From $204 per night (USD)Expedia
From $284 per night (USD)VRBO
1 bedroom, 1 bathroom cottage with sleeper sofa & full kitchen.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Bluemoon Cottage is a perfect getaway for a couple or friends visiting Ashland, OR. The one bedroom (queen bed), one ...
From $284 per night (USD)VRBO
From $1114 per night (USD)Expedia
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
About this space The house has five bedrooms, each with its own private bathroom. A gourmet kitchen with a large dining ...
From $1114 per night (USD)Expedia
From $657 per night (USD)VRBO
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 14
About this space The Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, ...
From $657 per night (USD)VRBO
From $200 per night (USD)Expedia
2 bedroom cabin plus loft, huge deck, lodge-style furnishings.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtow ...
From $200 per night (USD)Expedia
From $699 per night (USD)VRBO
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 22
What this place offers : 8 Bedrooms, 5 bathrooms, laundry , Washing machine , Entertainment , TV , Heating an ...
From $699 per night (USD)VRBO
From $312 per night (USD)Expedia
2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space This two-story, modern home has three bedrooms. The primary bedroom has a king-sized bed and the guest ...
From $312 per night (USD)Expedia
From $443 per night (USD)VRBO
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
About this space This spacious five bedroom historic home has been fully renovated, has brand new furnishings, and is p ...
From $443 per night (USD)VRBO
From $250 per night (USD)Expedia
Spacious 2 bedroom historic home with two king beds and kitchenette.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space One block from OSF. Enjoy a relaxing getaway at the Pioneer House. originally built in 1904. Up to six ...
From $250 per night (USD)Expedia
From $247 per night (USD)VRBO
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic home - One block from OSF. Easy access to dining, wine tasting, and shopping. Originally built in 1904, this ...
From $247 per night (USD)VRBO
From $336 per night (USD)Expedia
Luxury condo with king bedroom, two bathrooms, full kitchen.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Plaza North is a luxury vacation destination located in the heart of downtown Ashland, just steps to the culinary deligh ...
From $336 per night (USD)Expedia
Click For PricingVRBO
3 Bedroom Victorian a few blocks from Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream rental in the historic district of Ashland, Oregon! This SPACIOUS 3 BDR 1904 Queen Anne Victorian ...
Click For PricingVRBO
From $110 per night (USD)VRBO
Light-filled, upper story flat, walking distance to Oregon Shakespeare Festival
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
(Note: yes, the entire flat is yours. Your private entrance is completely separate from the downstairs flat. No adjoinin ...
From $110 per night (USD)VRBO
Click For PricingVRBO
Private and quiet luxury studio suite on three acres overlooking Ashland.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on three acres overlooking Ashland, yet just minutes away from everything Ashland has to offer, this private lux ...
Click For PricingVRBO
From $475 per night (USD)Expedia
The Blue Moon House has 5 bedrooms, each with a private bath, plus kitchen, dining and living area.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Built in the early 1900's and fully renovated. The Blue Moon House has it all! Five bedrooms offering a king or queen b ...
From $475 per night (USD)Expedia
Click For PricingVRBO
Quiet Bellview Retreat Rear
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located on the south edge of Ashland, and set back from the street, this quiet one-bedroom is fully furnished and privat ...
Click For PricingVRBO
From $322 per night (USD)Expedia
Hanna's House | 1 block to downtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Hanna's House, a one-bedroom retreat just blocks and walking distance from downtown Ashland. Featuring a lu ...
From $322 per night (USD)Expedia
From $419 per night (USD)VRBO
Charming house two blocks from downtown Ashland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comf ...
From $419 per night (USD)VRBO
From $73 per night (USD)Expedia
Cozy European Cottage 2 bd + 1 bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Discover the charm of Ashland from this beautifully appointed 2-bedroom, 1-bath Additional Dwelling Unit—a private haven ...
From $73 per night (USD)Expedia
From $328 per night (USD)VRBO
Centrally located Historic Home with parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience history and enchantment at our Ashland, Oregon home built in 1887. Our home is minutes walk to everything and ...
From $328 per night (USD)VRBO
Click For PricingExpedia
Brand New Crowson Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About this space The Crowson Cottage is located in a beautiful private setting, close to many amazing wineries and withi ...
Click For PricingExpedia
From $143 per night (USD)VRBO
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Considering the central location of this little gem, it is amazingly peaceful. There is a long driveway that takes you ...
From $143 per night (USD)VRBO
From $235 per night (USD)VRBO
Beautiful little place. Walk to town and theaters!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nice things come in small packages! While this home is small it is delightfully eloquent. Sparkling clean with a moder ...
From $235 per night (USD)VRBO
From $233 per night (USD)VRBO
Chateau Herbe ~ Oberon Suite w/ Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This chateau apartment is nothing short of magical. Enjoy a tranquil environment with breathtaking views of the estate g ...
From $233 per night (USD)VRBO
From $753 per night (USD)Expedia
Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.\n
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Driving through the front gates you will find this Gorgeous and Stunning, completely refurbished, updated farmhouse orig ...
From $753 per night (USD)Expedia
From $177 per night (USD)VRBO
Chateau Herbe ~ Rosalind Carriage House beautiful 1 bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About the Space: This comfortable carriage house apartment is nestled in a gated castle community that boasts classical ...
From $177 per night (USD)VRBO
From $207 per night (USD)Expedia
Chateau Herb ~ Juliet Carriage House Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Carriage House Juliet at Chateau Herbe! A state-of-the art contemporary castle estate with stunning groun ...
From $207 per night (USD)Expedia
From $166 per night (USD)VRBO
Chateau Herb ~ Miranda Carriage House Apt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Carriage House Miranda at Château Herbe, A contemporary retreat nestled within a one-of-a-kind castle est ...
From $166 per night (USD)VRBO
From $94 per night (USD)Expedia
Chateau Herbe ~ Vienna Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wake up to breathtaking views of classical gardens and mountains beyond. This spacious private room has a private en sui ...
From $94 per night (USD)Expedia
From $106 per night (USD)VRBO
Chateau Herbe ~ Athens Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wake up to breathtaking views of classical gardens and mountains beyond. This spacious private room has a private en sui ...
From $106 per night (USD)VRBO
From $77 per night (USD)Expedia
Florence Room at Chateau Herbe
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax in the window seat while taking in breathtaking views of classical gardens and mountains beyond. This private room ...
From $77 per night (USD)Expedia