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    Ashland Holiday Rentals

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      Travellers to Ashland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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      Blue Moon House & Cottage ~ Just 5 Blocks from OSF1 / 29
      7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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      ArtYcottage UNBELIEVEABLE...1 / 16
      (19)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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      Falcon Heights West - #2031 / 24
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      The Pioneer House (North Suite) - Closest to OSF!1 / 14
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      About this property
      Fully renovated - available May 1st, 2018 It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      RedTail Suites ~ Entire Home ~ Sleeps 12 ~ Tesla Station1 / 41
      4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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      About this property
      Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
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      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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      #33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub1 / 23
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Oak Street Cottages - Studio1 / 10
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Water Suite Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a kitchenette, living room with sofa-bed, flat panel 4K TV, one...
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      Ashland, Oregon 97520
      Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Anne Hathaway's House1 / 46
      7 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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      The Anne Hathaway House was built in 1908 as a boarding house for travelers. David and Deedie Runkel purchased the home in 2002 and continue to operate it today. Located just four short blocks from the Oregon Shakespeare Festival, the Anne Hathaway House is ideal for large groups of theater goers,...
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      Ashland, Oregon 97520
      Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 12
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      '1900' House and Cottage ~ Near OSF ~ Sleeps 101 / 22
      4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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      3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
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      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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      #52 The Cabins at Hyatt Lake - Sleeps 4 -Lake View1 / 43
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      The Pioneer House (South Suite) - Closest to OSF!1 / 14
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      About this property
      Fully renovated - available May 2018 It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      The Pioneer - Craftsman House - Closest to OSF!1 / 23
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      About this property
      It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private,...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      The High Street Cottage An Artists' Garden Cottage1 / 10
      (7)Excellent
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      The Unique High Street Cottage
      Reviewed 24 March 2018
      The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint Peter met him at the Pearly Gates and gave him a tour of his new eternal home. When...
      Perfect space within walking distance of everything
      Reviewed 4 March 2016
      My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
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      About this property
      Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      #44 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub1 / 30
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      '1900' House ~ Near OSF~Sleeps 81 / 17
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      About this property
      3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown1 / 13
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      #49 The Cabins at Hyatt Lake - Sleeps 4 - Private1 / 26
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Book your reservation for 2 nights and let us know you’d like the 3rd night free, we’ll enter that for you!! Just eighteen miles east of downtown Ashland are The Cabins at...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Hopyard View Farm ~ A Farm Experience in Ashland!1 / 26
      2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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      A working family farm just 5 minutes from downtown Ashland. Views of mountains can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside. This suite is bright and comfortable, with private entrance. It includes a Master Bedroom (queen bed), a...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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      Falcon Heights West - #2021 / 16
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Cable/satellite TV
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      • Balcony
      • Private Garden
      • Terrace
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #40 The Cabins at Hyatt Lake-Sleeps 6-Pet Friendly1 / 14
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your *PET FRIENDLY* Hyatt...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #51 & #52 Hyatt Lake Compound~Sleeps 10~Lake View1 / 39
      3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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      Eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabins with a Hot Tub and lake views! The master bedrooms have queen beds. The sleeping loft in #51 has a queen and full bed. #52 has a...
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      Ashland, Oregon 97520
      Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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      #39 & #40 Hyatt Lake Compound - Sleeps 121 / 33
      4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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      Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Welcome to your Hyatt Lake Cabin with Hot Tub! The master bedrooms both have a queen size bed, and the sleeping lofts both have two full beds. Full kitchen, dining room, and bathroom. The cabins both have bbqs, decks,...
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      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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      RedTail Suites~'Red' McCall Suite~Tesla Station1 / 19
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      Sleeps 6 - Tesla Charging Station Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Oak Tower Townhouse-1.5 Blocks to OSF (Sleeps 8)1 / 12
      2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      About this property
      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Tower Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the Theaters. The home features a full kitchen, a patio, two...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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      Falcon Heights East - #2021 / 20
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #32 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub1 / 21
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Lori Lanes 'Romeo Cottage' ~ 2 Bedroom ~ Downtown1 / 15
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      About this property
      Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      2nd Street Cottages, HERITAGE HOUSE1 / 16
      (6)Excellent
      4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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      • Cable/satellite TV
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      Another wonderful stay!
      Reviewed 31 October 2018
      I have stayed at 2nd Street Cottages before and it continues to be our favorite vacation rental in Ashland. Such a well kept and beautiful Cottage. The owner pays such great...
      Perfection
      Reviewed 15 April 2017
      I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
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      About this property
      THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
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      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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      Bel Canto ~Stunning Views from Ashland’s Hillside1 / 15
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      High above the hamlet of Ashland sits Bel Canto, a quiet home nestled in the hillside with stunning views of the charming town below. This immaculate space is situated on the lower level of the owner's home with private entry. Although you’ll feel a million miles away in this peaceful sanctuary,...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      '1900' Guest House ~ Near OSF1 / 12
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply This home is brand new to the vacation rental market and is everything a family or small group is looking for. Close to restaurants and retailers... and less than five blocks...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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      Falcon Heights East - #2041 / 25
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      Pet friendly
      Kid friendly
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      About this property
      Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Oak Sherwin House- 1.5 Blocks from OSF (Sleeps 11)1 / 14
      2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Built in the late 1800's, the Sherwin House is in the heart of Ashland and is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, a front yard with seating, two private...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
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      Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF1 / 10
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      The Blue Moon Cottage is attached to the main home but has two private entrances. It offers a full kitchen, a gas fireplace, air conditioning, a separate bedroom with a comfy queen bed, a full bath with shower/tub combination and a private patio. There is also a flat screen television in the living...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      Oak Lawn Cottage ~ 1.5 Blocks to OSF (Sleeps 6)1 / 15
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      About this property
      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Lawn Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, living room with fireplace, flat panel TV, a patio, two...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Falcon Heights West - #2011 / 20
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Balcony
      • Cable/satellite TV
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      • Private Garden
      • Terrace
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
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      Location Information
      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      RedTail Suites~Orliena Suite (New)~Tesla Station1 / 19
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Terrace
      • Air Conditioning
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      • Mountain Views
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      Suitability
      Pet friendly
      Kid friendly
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      About this property
      Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
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      Ashland, Oregon 97520
      Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
      (7)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Cable/satellite TV
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      Pet friendly
      Kid friendly
      Smoking allowed
      Great Place!
      Reviewed 24 September 2015
      Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
      Cute place
      Reviewed 6 May 2015
      Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
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      About this property
      Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Oak Hideaway Cottage- 1.5 Blocks to OSF (Sleeps 6)1 / 10
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      Smoking allowed
      About this property
      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, these cottages are one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, large living room with fireplace, flat panel TV, patio,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #39 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub1 / 15
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Hot Tub
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      Pet friendly
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      Smoking allowed
      About this property
      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #47 & 48 Hyatt Lake Compound - Sleeps 91 / 20
      4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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      • Cable/satellite TV
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      About this property
      Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Hyatt Lake Cabin Compound! Two cabins connected by a common deck. Two full kitchen, dining rooms, and two bathrooms. Two master bedrooms (queen beds) and two...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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      #46 The Cabins at Hyatt Lake - Sleeps 5 - Hot Tub1 / 24
      (1)Excellent
      2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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      Magical Birthday Weekend getaway
      Reviewed 1 week ago
      The boyfriend and I wanted to get away from life for a long weekend for my birthday. The cabin was exactly as described, with a cute little sleeping loft, with a video game...
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      About this property
      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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      Whispering Pines Cabin Retreat ~ Pet Friendly1 / 31
      3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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      • Washer
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      About this property
      Located just 20 miles from downtown Ashland, Whispering Pines Cabin is situated on private acreage adjacent to Hyatt Lake. This cabin is very private and sleeps up to 12 people, making it the perfect getaway for a large family or group. Swim, fish, or paddle on the lake in the summer or play in the...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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      Aspen Canyon Studio1 / 20
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      About this property
      Park-like setting, high above Ashland, yet very close to town Tucked away in a canyon filled with Aspen and Pine trees, this quiet retreat is conveniently located just a five-minute drive from downtown Ashland. Guests have access to the grounds which are located in a well-maintained, park-like...
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      Location Information
      Ashland, Oregon 97520
      Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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      #45 The Cabins at Hyatt Lake-Sleeps 41 / 13
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Each Hyatt Lake cabin comes with wireless internet access, flat panel satellite TV, private deck, and lakefront or forest views. If you choose to dine out, The GreenSprings Inn...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      Walk to Downtown/Theaters from this Charming Home1 / 8
      (1)Excellent
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      Smoking allowed
      Great time in Ashland
      Reviewed 8 July 2018
      The location was terrific and close to downtown but very quiet and peaceful. The home was lovely, well done and plenty of space for our group. We loved the porch!!! All the...
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      About this property
      Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Mountain Pine Cabin - Sleeps 6 - Pet Friendly1 / 27
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Cable/satellite TV
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      Pet friendly
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      Smoking allowed
      About this property
      Just twenty miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! ALL NEW! Welcome to your Hyatt Lake Cabin with lake views! Two bedrooms, each with a queen size bed. There is also a queen air mattress. Full kitchen, dining...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #51 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub1 / 26
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Grill
      • Hot Tub
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      Pet friendly
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      Smoking allowed
      About this property
      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your Hyatt Lake Cabin with a Hot...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      #47 The Cabins at Hyatt Lake - Sleeps 5 - Hot Tub1 / 23
      2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!! Welcome to your PREMIUM Hyatt Lake...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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      #48 The Cabins at Hyatt Lake - Sleeps 4 - Hot Tub1 / 23
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      • DVD Player
      • Parking
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      3rd Night Free!!! October 1st through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Book your reservation for 2 nights and let us know you’d like the 3rd night free, we’ll enter that for you!! Just eighteen miles east of downtown Ashland are The Cabins at...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      Blue Moon House ~ Just Five Blocks from OSF!1 / 19
      5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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      About this property
      Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood... Built in the early 1900's and fully renovated the Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a...
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      Ashland, Oregon 97520
      Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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      1
      Ashland Holiday Rentals

      Are you looking for the perfect holiday 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 holiday 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 holiday 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 holiday 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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