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Ashland

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Ashland Holiday Rentals

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Ashland Vacation Rentals

Are you looking for the perfect vacation rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect vacation spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a vacation to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.

Ashland Activities

If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home vacation rental, plan your day around the activities that suit you best!

Romancing Ashland

Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.

Ashland is for Skiing and Golf

With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.

 
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17 Trusted Ashland Area Rentals
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€132 - €188
Minimum rental - 2 nights
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
€188
Minimum rental - 3 nights
Check availability
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Special offer details »
Night:
€132 - €188
Week:
€791 - €1,130
Minimum rental - 2 nights
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
€173 - €203
Minimum rental - 2 nights
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 5
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
€75 - €124
Week:
€527 - €746
Minimum rental - 2 nights
Check availability
  • Cabin Holiday Rental
  • 4 Bedrooms, sleeps 16
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
€150 - €222
Week:
€1,194 - €1,431
Minimum rental - 2 nights
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
€136 - €173
Minimum rental - 2 nights
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€68 - €98
Minimum rental - 2 nights
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 6 Bedrooms, sleeps 14
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
€102 - €509
Minimum rental - 1 night
Check availability
Real log cabin, Ashland
United States, Oregon, Ashland Holiday Rentals
  • Cabin Holiday Rental
  • 3 Bedrooms, sleeps 8
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€121
Week:
€678
Minimum rental - 3 nights
Check availability
  • Cabin Holiday Rental
  • 3 Bedrooms, sleeps 8
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
€87 - €139
Week:
€606 - €885
Minimum rental - 1 night
Check availability
Blue Moon B&B, Ashland
United States, Oregon, Ashland Holiday Rentals
  • Guest Room
  • 6 Bedrooms, sleeps 14
  • 6 Bathrooms
  • Owner
EMAIL OWNER
Night:
€52 - €181
Minimum rental - 1 night
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
€113 - €188
Week:
€678 - €1,130
Minimum rental - 2 nights
Check availability
United States, Oregon, Ashland Holiday Rentals
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€136 - €166
Minimum rental - 2 nights
Check availability

The following rentals are within 30 kilometers of Ashland, Oregon.

  • Holiday Rental House
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
€94 - €132
Week:
€716 - €791
Minimum rental - 1 night
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Check availability
  • Holiday Rental House
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€67 - €75
Week:
€414 - €471
Minimum rental - 2 nights
Check availability

Ashland Holiday Rental Advice

Posted by corksniffer, 31 Jul 2009
... mid-August. Staying in a vacation rental with kitchenette to save $$ on food - eat in, pack lunches, so on. Problem is no access to a swimming pool with the vacation rental. Any ideas on where we can take a swim in town or near town? We're big fans of ... more
Posted by irishkat, 16 Jul 2009
... romantic B&B, inn, hotel or vacation rental? 2) What is the best play this year at the festivle (we will be there on a fri/sat nights) 2) What is the 'not to miss' restaurant. We like all types of food! Thank you all for your help! Cheers, Irishkat ... more
Posted by ScarlettO1, 27 May 2006
The post I was referring to was last summer :) We spent a year in Florida before moving here to Portland, so sharks became a new and unpleasant reality. I am quite happy here in my apartment in Portland, not a shark or alligator in sight :D ... more
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