Jackson Area Rentals
From $182 per night (USD)VRBO
Monthly Rental Circular House blocks to Downtown & Oregon Shakespeare Festival
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A unique circular single-family house just blocks from Ashland's downtown dining & entertainment, Lithia Park, and the r ...
From $182 per night (USD)VRBO
From $110 per night (USD)Expedia
Light-filled, upper story flat, walking distance to Oregon Shakespeare Festival
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
(Note: yes, the entire flat is yours. Separate, private entrance from the downstairs flat. No adjoining doors.) The open ...
From $110 per night (USD)Expedia
From $256 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 $256 per night (USD)VRBO
From $127 per night (USD)VRBO
Comfortable, Private Guest Lodging
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Excellent value, suite in building separate from the house. Comfortable, spacious, clean with high-quality queen bed, pu ...
From $127 per night (USD)VRBO
From $61 per night (USD)VRBO
1-bedroom apartment just 6 minutes drive to Lithia & Driveway Fields
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Extended stay ( 2 weeks or more) furnished 1 bedroom apartment above my shop adjacent to my house. Secure with locked ga ...
From $61 per night (USD)VRBO
From $400 per night (USD)Expedia
A beautiful Skyfall Landing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled on 20 acres near the famous Rogue River and Crater Lake, this luxury privately accessed home will feel like a sp ...
From $400 per night (USD)Expedia
From $269 per night (USD)VRBO
The Shady Knoll - Peace & Quiet near the Rogue River!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax and Unwind at this peaceful retreat. Near the Rogue River & Crater Lake National Park, this beautiful property is ...
From $269 per night (USD)VRBO
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Modern Farmhouse on Emigrant Creek
- 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 ...
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From $253 per night (USD)VRBO
🌟 🥂 Medford’s BEST 📣 🌟 💕Clean, Modern, Private💕
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Simple and clean, with a hidden, private driveway in a safe and secure area of North East Medford. This home is only a f ...
From $253 per night (USD)VRBO
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Swiss Arbor Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Nested on an oak tree lined street in Old East Medford where people take leisurely walks and spot turkeys wandering abou ...
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From $183 per night (USD)VRBO
Valley Top Private Oasis 🌲
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled atop a private mountaintop property, this charming cottage offers solitude and breathtaking views. It has: -one ...
From $183 per night (USD)VRBO
From $142 per night (USD)Expedia
Tiny Living at its Finest… 🐞
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
🐞 Meet Ladybug 🐞! This ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ 2022 tiny home boasts all of 128 square feet in bottom and a loft approx 80 mo ...
From $142 per night (USD)Expedia
From $181 per night (USD)VRBO
Nancy's Garden Cottage - 1. 5 Blocks to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We are located in the heart of Ashland. Only 1.5 blocks from Downtown. Enjoy the open Garden and Great location to all R ...
From $181 per night (USD)VRBO
From $244 per night (USD)Expedia
Modern 3 bedroom close to Asante hospital!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located within walking distance of Asante Medical Center and other medical offices, this 3 bedroom home boasts 4 parking ...
From $244 per night (USD)Expedia
From $1030 per night (USD)VRBO
Main Residence: 5 beds, 5 baths, sleeping porches, & full kitchen.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
Located adjacent to the historic Hillcrest Orchard Estate and RoxyAnn Winery was designed by well known architect Frank ...
From $1030 per night (USD)VRBO
From $337 per night (USD)Expedia
The Cottage: One bedroom w\/mini fridge & private bath.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This historic little cottage boasts an incredible location for wine tasting and gorgeous views. Adjacent to the historic ...
From $337 per night (USD)Expedia
From $568 per night (USD)VRBO
Indulgent Retreat: Pool, Hot Tub, Sauna
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Luxury 3BR escape with pool, and sauna awaits near the Oregon Shakespeare Festival. Indulge in refined living with 3 kin ...
From $568 per night (USD)VRBO
From $535 per night (USD)Expedia
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 $535 per night (USD)Expedia
From $249 per night (USD)VRBO
Clean, pet friendly, 2-Bedroom Cottage with large fenced yard.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Comfortable and clean, this pet friendly two bedroom cottage has the right balance of vintage charm and modern convenien ...
From $249 per night (USD)VRBO
From $325 per night (USD)Expedia
Perfect for Large Families or Work Teams. Coffee Bar-Gas FP-Cornhole-Firepit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
-No Checkout Chores- This place is perfect for a large group to relax and hang out after a day or exploring the area. N ...
From $325 per night (USD)Expedia
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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 ...
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From $102 per night (USD)Expedia
Gorgeous custom Airstream with spectacular views only 4 mi. to Ashland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one-of-a-kind completely renovated classic trailer is the perfect getaway accommodation. Situated on a 5 acre Tusca ...
From $102 per night (USD)Expedia
From $239 per night (USD)VRBO
Feels like Home-Very Comfy and Well Stocked-Centrally Located-Walk to Major Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
-No Checkout Chores- Lotus House is a very comfortable home that is ideal for relaxing after exploring all that our are ...
From $239 per night (USD)VRBO
From $208 per night (USD)Expedia
Howell House-The Perfect Getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled 1965 Farmhouse style home with an open Floor plan. This home is 962 sq ft With a huge backyard. The TV o ...
From $208 per night (USD)Expedia
From $136 per night (USD)VRBO
Country Setting, five minute drive to Ashland close to Emigrant Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This upstairs 500 sq. ft. studio has its own private entrance and is complete with balcony. (Great for barbecuing or sta ...
From $136 per night (USD)VRBO
From $497 per night (USD)Expedia
Charming 2-bedroom house in the tranquil Applegate. In the heart of wine country
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in the Applegate at this terrific house. With two queen bedrooms, a bathroom equipped with a bidet and shower, an ...
From $497 per night (USD)Expedia