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Ashland Vacation Rentals

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    Check prices for these dates, December 14–15, 2026

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    Our top choices for Ashland vacation homes

    1. Whimsy on B

    A garden with a stone pathway, various plants, a barbecue grill, and a bicycle.

    2. Barclay Klum House by WanderLodges

    A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

    3. Hanna's House by WanderLodges

    A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

    4. Whimsy On B 2br & Studio

    A wooden door with a small window above it, a porch with a wooden railing, and a green hose on the right side.

    5. Savage Upon Siskiyou

    A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

    6. Grandview of Ashland

    A deck with a fire pit, outdoor seating, and a view of the countryside.

    7. The Mountain Ave House by WanderLodges

    A modern kitchen with wooden beams, a dining area with a rug, and a large island.

    8. Hanna`s House | Downtown Retreat, Steps to OSF

    A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

    9. East Main Downtown Bungalow

    A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

    10. Ashland Cottage | Walk to Downtown & Coffee

    A modern kitchen with a central island, bar stools, and a built-in oven.

    11. Swank Boutique Suites | King Suite | DT Ashland

    A residential property with a white picket fence, a brick pathway, and a wooden pergola adorned with string lights.

    12. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

    A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

    13. Moody Ashland Escape: Luxe Suite, Copper Tub

    A modern bathroom with a glass shower enclosure, a sink with a mirror, and a decorative wall with floral patterns.

    14. Hot tub | Sauna |Firepit |Sleeps 6!

    A deck with a fire pit, seating, and a view of the mountains.

    15. Park & Pillow - Bright 2BR Escape, Stroll to OSF Theaters & Town

    A modern kitchen with white cabinetry, granite countertops, a stainless steel range hood, and an LG oven.

    16. Chateau Herb ~ Miranda Carriage House Apt

    Exterior

    17. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

    A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

    18. Whimsy on B | 2BR Steps to Downtown

    A garden with a white fence, green hedges, and purple flowering trees.

    19. Downtown Ashland House - Walk to Plaza and OSF!

    A two-story house with a porch, a wooden fence, and a paved driveway.

    20. Savage Upon Siskiyou | Prime OSF Location

    A two-story house with a porch, a small garden, and a metal fence.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Ashland

    World-class Shakespeare performances unfold in outdoor theatres surrounded by mountain views from June through October. Lithia Park's trails wind along Ashland Creek, perfect for morning walks before browsing the downtown galleries and craft breweries.

    See all hotels in Ashland

    A stone bridge over a calm stream with autumn leaves.

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