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Ashland Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
171 rentals in Ashland.
Charming home, w/hot tub, close to downtown Pet-Friendly!, vacation rental in Ashland
Charming home, w/hot tub, close to downtown Pet-Friendly!, vacation rental in Ashland
Charming home, w/hot tub, close to downtown Pet-Friendly!, vacation rental in Ashland

Charming home, w/hot tub, close to downtown Pet-Friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland
Premier Downstairs Flat in Perfect Down Town Location, vacation rental in Ashland

Premier Downstairs Flat in Perfect Down Town Location

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall, vacation rental in Ashland

Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Madrone House, Country Getaway with Mountain Views and Fresh Air., vacation rental in Ashland
The Madrone House, Country Getaway with Mountain Views and Fresh Air., vacation rental in Ashland
The Madrone House, Country Getaway with Mountain Views and Fresh Air., vacation rental in Ashland

The Madrone House, Country Getaway with Mountain Views and Fresh Air.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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East Main Downtown Bungalow, vacation rental in Ashland
East Main Downtown Bungalow, vacation rental in Ashland
East Main Downtown Bungalow, vacation rental in Ashland

East Main Downtown Bungalow

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ashland Retreat: Cozy Chic Studio Haven, vacation rental in Ashland
Ashland Retreat: Cozy Chic Studio Haven, vacation rental in Ashland
Ashland Retreat: Cozy Chic Studio Haven, vacation rental in Ashland

Ashland Retreat: Cozy Chic Studio Haven

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!, vacation rental in Ashland
Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!, vacation rental in Ashland
Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!, vacation rental in Ashland

Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland
Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland
Downtown Ashland Earth spa unit with private patio, vacation rental in Ashland

Downtown Ashland Earth spa unit with private patio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland
Country's Edge Rooms in just outside of Ashland, convenient for travel, vacation rental in Ashland

Country's Edge Rooms in just outside of Ashland, convenient for travel

Rental Home
1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
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Lodge Room 2 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 2 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 2 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 2 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 7 at Green Springs Inn, vacation rental in Ashland
Lodge Room 7 at Green Springs Inn, vacation rental in Ashland
Lodge Room 7 at Green Springs Inn, vacation rental in Ashland

Lodge Room 7 at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lodge Room 6 at Green Springs Inn, vacation rental in Ashland
Lodge Room 6 at Green Springs Inn, vacation rental in Ashland
Lodge Room 6 at Green Springs Inn, vacation rental in Ashland

Lodge Room 6 at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 1 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 1 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 4 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 4 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 4 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 4 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 3 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 3 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 3 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 3 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 8 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 8 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 8 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 8 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lodge Room 5 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 5 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland
Lodge Room 5 with Jacuzzi Tub at Green Springs Inn, vacation rental in Ashland

Lodge Room 5 with Jacuzzi Tub at Green Springs Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views, vacation rental in Ashland
The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views, vacation rental in Ashland
The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views, vacation rental in Ashland

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sage Ashland Cottage, vacation rental in Ashland
Sage Ashland Cottage, vacation rental in Ashland
Sage Ashland Cottage, vacation rental in Ashland

Sage Ashland Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Studio Retreat: Pet-Friendly Comfort, vacation rental in Ashland
Studio Retreat: Pet-Friendly Comfort, vacation rental in Ashland
Studio Retreat: Pet-Friendly Comfort, vacation rental in Ashland

Studio Retreat: Pet-Friendly Comfort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, vacation rental in Ashland
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, vacation rental in Ashland
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean, vacation rental in Ashland

The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Agate Flats Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Agate Flats Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Agate Flats Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Agate Flats Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Nancy's Garden Cottage -1. 5 Blocks to Downtown, vacation rental in Ashland
Nancy's Garden Cottage -1. 5 Blocks to Downtown, vacation rental in Ashland
Nancy's Garden Cottage -1. 5 Blocks to Downtown, vacation rental in Ashland

Nancy's Garden Cottage -1. 5 Blocks to Downtown

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland
Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland
Charming Space Next to Everything, Walk Anywhere!, vacation rental in Ashland

Charming Space Next to Everything, Walk Anywhere!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Parsnip Lakes Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Parsnip Lakes Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Parsnip Lakes Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Parsnip Lakes Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland
1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station, vacation rental in Ashland

1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Boccard Point Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Boccard Point Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Boccard Point Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Boccard Point Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Swank House on Main St in Ashland, vacation rental in Ashland
Swank House on Main St in Ashland, vacation rental in Ashland
Swank House on Main St in Ashland, vacation rental in Ashland

Swank House on Main St in Ashland

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Helman Street Penthouse with a View, vacation rental in Ashland
Helman Street Penthouse with a View, vacation rental in Ashland
Helman Street Penthouse with a View, vacation rental in Ashland

Helman Street Penthouse with a View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ashland Duo: Your Downtown Duplex, vacation rental in Ashland
Ashland Duo: Your Downtown Duplex, vacation rental in Ashland
Ashland Duo: Your Downtown Duplex, vacation rental in Ashland

Ashland Duo: Your Downtown Duplex

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Ave House by WanderLodges, vacation rental in Ashland
Mountain Ave House by WanderLodges, vacation rental in Ashland
Mountain Ave House by WanderLodges, vacation rental in Ashland

Mountain Ave House by WanderLodges

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ashland's Mountain View Vacation Rental., vacation rental in Ashland
Ashland's Mountain View Vacation Rental., vacation rental in Ashland
Ashland's Mountain View Vacation Rental., vacation rental in Ashland

Ashland's Mountain View Vacation Rental.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful and comfy cabin near Hyatt lake and reservoir., vacation rental in Ashland
Peaceful and comfy cabin near Hyatt lake and reservoir., vacation rental in Ashland
Peaceful and comfy cabin near Hyatt lake and reservoir., vacation rental in Ashland

Peaceful and comfy cabin near Hyatt lake and reservoir.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Artsy Downtown Historical House: Steps to Shakespeare, vacation rental in Ashland
Artsy Downtown Historical House: Steps to Shakespeare, vacation rental in Ashland
Artsy Downtown Historical House: Steps to Shakespeare, vacation rental in Ashland

Artsy Downtown Historical House: Steps to Shakespeare

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland, vacation rental in Ashland
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland, vacation rental in Ashland
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland, vacation rental in Ashland

Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Callahan's House, vacation rental in Ashland
Callahan's House, vacation rental in Ashland
Callahan's House, vacation rental in Ashland

Callahan's House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland
Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland
Spacious B Street Beauty, Around the Corner from Festival, vacation rental in Ashland

Spacious B Street Beauty, Around the Corner from Festival

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ashland Lodge w/ Lake Views & Game Room Loft, vacation rental in Ashland
Ashland Lodge w/ Lake Views & Game Room Loft, vacation rental in Ashland
Ashland Lodge w/ Lake Views & Game Room Loft, vacation rental in Ashland

Ashland Lodge w/ Lake Views & Game Room Loft

Rental Home
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Serenity Awaits: Pool, Hot Tub, Sauna, Gym, vacation rental in Ashland
Serenity Awaits: Pool, Hot Tub, Sauna, Gym, vacation rental in Ashland
Serenity Awaits: Pool, Hot Tub, Sauna, Gym, vacation rental in Ashland

Serenity Awaits: Pool, Hot Tub, Sauna, Gym

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Retreat in Style: 4BR Jewel, Pool, HotTub, vacation rental in Ashland
Retreat in Style: 4BR Jewel, Pool, HotTub, vacation rental in Ashland
Retreat in Style: 4BR Jewel, Pool, HotTub, vacation rental in Ashland

Retreat in Style: 4BR Jewel, Pool, HotTub

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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The Peerless Hotel | Junior Suite #5 | Jetted Tub | Historic District, vacation rental in Ashland
The Peerless Hotel | Junior Suite #5 | Jetted Tub | Historic District, vacation rental in Ashland
The Peerless Hotel | Junior Suite #5 | Jetted Tub | Historic District, vacation rental in Ashland

The Peerless Hotel | Junior Suite #5 | Jetted Tub | Historic District

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University, vacation rental in Ashland
2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University, vacation rental in Ashland
2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University, vacation rental in Ashland

2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room., vacation rental in Ashland
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room., vacation rental in Ashland
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room., vacation rental in Ashland

Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.

Condo/Apartment
8 bedrooms
9 bathrooms
Sleeps 14
Match: Sleeps
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Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, vacation rental in Ashland

Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland
230-Downstairs-Duplex-Private Bathroom-Mountain View, vacation rental in Ashland

230-Downstairs-Duplex-Private Bathroom-Mountain View

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chinquapin Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Chinquapin Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland
Chinquapin Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn, vacation rental in Ashland

Chinquapin Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 171
Frequently Asked Questions about Ashland






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.