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A stone bridge over a calm stream with autumn leaves.

Ashland Vacation Rentals

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    Check prices for these dates, December 13–14, 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. 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.

    4. Grandview of Ashland

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

    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. 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.

    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. 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.

    12. Swank Suites | King with Lux Tub

    A patio area with outdoor seating, a small garden, and string lights.

    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. 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.

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

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

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

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

    17. Chateau Herb ~ Miranda Carriage House Apt

    Exterior

    18. Whimsy on B | 2BR Steps to Downtown

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

    19. 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.

    20. Charming house two blocks from downtown Ashland

    A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

    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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