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Ashland Cottages

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$1,000+
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120 rentals in Ashland.
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The Ashland Cottage, walk to town
1 bedroom
2 bathrooms
Sleeps 4
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Craftsman Style Home In Country Setting
4 bedrooms
3 bathrooms
Sleeps 10
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Brand New Custom Ashland Home with Fantastic Mountain Views
2 bedrooms
2 bathrooms
Sleeps 4
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Hanna's House- Your Home Away from Home
1 bedroom
1 bathroom
Sleeps 3
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The Madrone House, New Country Getaway with Panoramic Views
3 bedrooms
3 bathrooms
Sleeps 9
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Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland
2 bedrooms
1 bathroom
Sleeps 4
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~AGC~- Carriage House -Best Location - 2bd/2bth -4 Blocks 2 Town, Lithia & ~OSF~
2 bedrooms
2 bathrooms
Sleeps 4
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The Ridgeview Lodge ~ Perfect for Family Events, Sleeps 15, Beautiful Views
3 bedrooms
4 bathrooms
Sleeps 13
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~AGC~ Oberon 4 Blocks 2 Downtown - Charming Cozy Private Stylish Shakespeare OSF
1 bedroom
1 bathroom
Sleeps 2
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ArtYcottage UNBELIEVEABLE...
2 bedrooms
2 bathrooms
Sleeps 4
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~AGC~-Romeo & Juliet - 4 Blocks to Downtown, Lithia Park & ~OSF~ Best Location
2 bedrooms
2 bathrooms
Sleeps 6
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Quiet and peaceful cottage close to downtown
1 bedroom
2 bathrooms
Sleeps 5
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Hyatt Prairie Mountain Cabin
3 bedrooms
2 bathrooms
Sleeps 8
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The Maple Apartment at Tudor House Vacation Rentals
2 bedrooms
2 bathrooms
Sleeps 6
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'Orchard Suite' Stay...Relax...Enjoy
1 bedroom
1 bathroom
Sleeps 7
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Hyatt Lake Mountain Retreat
3 bedrooms
1 bathroom
Sleeps 7
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Winter on PINE STREET! ASHLAND! COZY cottage near Lithia Park and Town!
1 bedroom
1 bathroom
Sleeps 2
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The Terra Cottage Inn a beautiful Luxury Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Private Suite Near Shakespeare
1 bedroom
1 bathroom
Sleeps 2
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Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!
6 bedrooms
3 bathrooms
Sleeps 11
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The Dogwood Suite at Tudor House Vacation Rentals
1 bedroom
2 bathrooms
Sleeps 5
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Magnificent, secluded, garden, private decks for families and pets.
1 bedroom
1 bathroom
Sleeps 4
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Charming, Comfortable Garden Studio Above The University.
1 bedroom
1 bathroom
Sleeps 3
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The High Street Cottage An Artists' Garden Cottage
2 bedrooms
1 bathroom
Sleeps 4
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Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
2 bedrooms
2 bathrooms
Sleeps 4
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2nd Street Cottages, HERITAGE HOUSE
4 bedrooms
3 bathrooms
Sleeps 8
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2nd Street Cottages, GARDEN SUITE
2 bedrooms
2 bathrooms
Sleeps 5
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Top floor of brand new duplex - walk to plays, SOU, Lithia Park
1 bedroom
1 bathroom
Sleeps 2
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Stay Ashland like never before. Explore days, campfire stars at night!
1 bedroom
1 bathroom
Sleeps 3
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#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub
2 bedrooms
1 bathroom
Sleeps 6
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Perfect vacation cottage
2 bedrooms
2 bathrooms
Sleeps 6
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#46 The Cabins at Hyatt Lake-Sleeps 5-Dog Friendly
2 bedrooms
1 bathroom
Sleeps 5
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Pelton Villa
4 bedrooms
3 bathrooms
Sleeps 8
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The Brenden House, Walk to Theaters
3 bedrooms
3 bathrooms
Sleeps 8
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#52 The Cabins at Hyatt Lake - Sleeps 4 -Lake View - Hot Tub
1 bedroom
1 bathroom
Sleeps 4
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Ashland Lodge w/ Lake Views, Patio & 5 Mtn Bikes!
4 bedrooms
3 bathrooms
Sleeps 13
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The Pioneer House -North Suite (Upstairs) - Closest to OSF!
2 bedrooms
1 bathroom
Sleeps 6
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The Pioneer - Craftsman House - Closest to OSF!
3 bedrooms
2 bathrooms
Sleeps 8
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NEW! Cottage w/Fireplace, Walk to Downtown Ashland
1 bedroom
1 bathroom
Sleeps 2
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#1D Hobart Peak ~ Green Springs Cabins ~ Jacuzzi Tub
2 bedrooms
1 bathroom
Sleeps 6
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Luxurious Home near Downtown Ashland and Theaters
3 bedrooms
2 bathrooms
Sleeps 9
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Walk to Downtown/Theaters from this Charming Home
2 bedrooms
1 bathroom
Sleeps 6
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Cattle View Ranch House
4 bedrooms
2 bathrooms
Sleeps 9
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The Aloha House ~ Hot Tub & Seasonal Pool
2 bedrooms
2 bathrooms
Sleeps 4
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#1B Soda Mountain ~ Green Springs Cabins ~ Jacuzzi Tub
2 bedrooms
1 bathroom
Sleeps 6
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#1 Lodge Room 1 ~ Green Springs Inn ~ Jacuzzi Bathtub
1 bedroom
1 bathroom
Sleeps 2
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Beautiful Apartment in Ashland
1 bedroom
1 bathroom
Sleeps 2
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#2E Agate Flats ~ Green Springs Cabins ~ Jacuzzi Tub
2 bedrooms
1 bathroom
Sleeps 6
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Stone's Throw Bungalow - Licensed, Private Garden
0 bedrooms
1 bathroom
Sleeps 2
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Earth King Suite with Jacuzzi
1 bedroom
1 bathroom
Sleeps 3
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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.
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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.