459+ Vacation Rentals & Holiday Homes in Ashland |
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Ashland Accommodations - Hotels & Rentals

About Ashland Vacation Rentals

Discover More than 459 Incredible Getaway Rentals Available in Ashland. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Ashland.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Ashland, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Ashland. The Average Size of Places to Stay Near Ashland is 699.57 ft², with Prices Averaging US $261 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Ashland. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Ashland

Type Count
Vacation Homes 188
Holiday Apartments 74
Cottages 34
Villas 3

Use these Quick Filters to Find a Vacation Rental in Ashland

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Ashland with Online Reservations.

Weather in Ashland, OR

View the weather forecast for Ashland before booking your Ashland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities AshlandGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World AshlandGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Oregon Shakespeare Festival
Mount Ashland Ski Area
Southern Oregon University
Lithia Park
Historic Pinehurst Inn
Ashland Library
Oregon Cabaret Theatre
Howard Prairie Lake
Comer Ski Lift
Allen Elizabethan Theatre
Emigrant Lake
Thomas Theatre
North Mountain Park
Angus Bowmer Theatre
Schneider Museum of Art
Lithia Artisans Market
Hyatt Reservoir
Bull Gap Lower Trailhead
Windsor Ski Lift
Ariel Ski Lift

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Tashi Choling Buddhist Center 374 Properties
Ariel Ski Lift 367 Properties
Windsor Ski Lift 367 Properties
Comer Ski Lift 367 Properties
Mount Ashland Ski Area 367 Properties
Historic Downtown District 305 Properties
Ashland Library 301 Properties
North Mountain Park 301 Properties
Angus Bowmer Theatre 300 Properties
Skidmore Academy Historic District 272 Properties
Historic Railroad District 57 Properties
Siskiyou-Hargadine Historic District 32 Properties

Frequently Asked Questions About Ashland?

What are the top hotels, lake houses & vacation rentals in Ashland?

We provide an array of great vacation destinations in Ashland. If you are looking to stay in or around the Ashland area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Ashland:

How many Hotels & Vacation Rentals have private pools in Ashland?

We have 4 Hotels & Vacation Rentals featuring a private pool in and near Ashland. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Ashland is best for families?

Searching for a family-friendly getaway in Ashland? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Ashland?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 459 in the Ashland area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Ashland.

Nearby Neighborhood (4) 
Neighborhood Property Count
Historic Downtown District Vacation Rentals in Medford, Oregon 305
Historic Railroad District Vacation Rentals in Medford, Oregon 57
Siskiyou-Hargadine Historic District Vacation Rentals in Medford, Oregon 32
Skidmore Academy Historic District Vacation Rentals in Medford, Oregon 272

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