Owner Direct Vacation Rentals in Ashland

The Best Owner Direct Vacation Rentals in Ashland. Explore thousands of vacation home rentals, large cabins, and villas near Ashland

Swank House on Main St in Ashland From US $527
         

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10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
The Ashland Cottage, walk to town From US $269
         

The Mountain Ave House by WanderLodges From US $439
         

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10.0 (7 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Pioneer Vacation Rentals - Pioneer South downtown Ashland From US $126
         

The Barn at Emigrant Creek From US $161
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Pioneer Vacation Rentals - Pioneer Craftsman House From US $374
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Ashland

Over 452+ Luxury Places to Stay in or Near Ashland
Luxury Ashland Mountain Escape: Pool, Hot Tub From US $1,079
         

9.4 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area. From US $1,071
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Ashland

Over 48+ Top-Rated Vacation Rentals with a Pool in or Near Ashland
Indulgent Retreat: 3 King Suites, Pool & Hot Tub From US $360
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Ashland Studio: King Bed, 1 mile from Plaza! From US $204
         

10.0 (25 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn From US $214
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Lodge Room 7 at Green Springs Inn From US $214
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Arden Forest Inn From US $212
         

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9.8 (103 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Country Willows Inn and Estate From US $186
         

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9.8 (33 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Ashland Luxury: 4 King suites, pool & hot tub From US $694
         

9.8 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Ashland

Over 160+ Pet-Friendly Vacation Rentals in or Near Ashland
Bluemoon Vacation Rentals - Bluemoon House From US $505
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Red Dragon House From US $160
         

10.0 (103 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
A Cowslip's Belle Inn From US $223
         

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9.8 (40 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Redtail Inn - 3 Suites Sleeps Up To 12 From US $398
         

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9.9 (11 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Courtside Cottage - WalkScore 93 - Dog Friendly From US $213
         

10.0 (59 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Ashland Bungalow downtown From US $122
         

9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluemoon Vacation Rentals - Bluemoon Cottage From US $265
         

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9.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Ashland on PetFriendly.io

Large Vacation Homes & Villas in Ashland

Over 43+ Large Vacation Homes & Villas in or Near Ashland
Abigail's Bed and Breakfast Inn From US $235
         

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9.7 (49 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Homey Rustic Cabin in the Cascades From US $352
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Mahar Homes - Plaza North on First From US $365
         

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9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Gorgeous Lakeside HOUSE + Indoor SAUNA! From US $357
         

8.8 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
European Style Straw Bale Retreat From US $384
         

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9.3 (4 Reviews)
Villa
  • Parking
  • View
  • Balcony/Terrace
Ashland Lodge w/Lake Views & Game Room Loft From US $549
         

10.0 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Cabins at Hyatt From US $204
         

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9.0 (3 Reviews)
Apartment
  • Parking
  • Balcony/Terrace
  • Security/Safety

Wheelchair Accessible Vacation Homes in Ashland

Over 30+ Wheelchair Accessible Vacation Homes in or Near Ashland
Bayberry Inn B&B and Oregon Wellness Retreat From US $294
         

10.0 (15 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Ashland private cottage with garden patio From US $176
         

9.8 (48 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Callahan's Mountain Lodge From US $146
         

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8.8 (1174 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites Ashland by IHG From US $140
         

8.8 (274 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
BookStayHop - Suite Windsor - Plaza North From US $335
         

5.0 (4 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
Stratford Inn From US $170
         

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8.6 (1385 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Windsor Inn From US $141
         

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8.5 (529 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Ashland Varoom and Airbnb Places to Stay Under $200

Over 187+ Ashland Varoom and Airbnb Places to Stay Under $200
Hanna's House by WanderLodges From US $197
         

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9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Lithia Springs Resort From US $156
         

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9.4 (1002 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Green Springs Inn From US $99
         

8.3 (141 Reviews)
Resort
  • Parking
  • Security/Safety
  • EV Charge Station
Ashland Commons Hostel From US $140
         

8.0 (46 Reviews)
Hostel
  • Parking
  • TV
  • View
Charming well appointed Cottage in Ashland (800 + sq. ft.) From US $103
         

Instantly Bookable Vacation Homes in Ashland

Over 261+ Instantly Bookable Vacation Homes in or Near Ashland
Custom Ashland Home with Fantastic Mountain Views From US $217
         

10.0 (99 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Centrally located Historic Home with parking From US $336
         

Hyatt Prairie Mountain Cabin From US $435
         

10.0 (57 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

About Ashland Vacation Rentals

With more than 461 Ashland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Ashland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Ashland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Ashland. Places to stay near Ashland are 700.67 ft² on average, with prices averaging $272 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Ashland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Ashland

Type Count
Vacation Homes 191
Holiday Apartments 73
Cabin Rentals 60
Hotels with Suites 57
Cottages 34
B&B 19
Others 11
Resorts 4
Villas 3
Hostels 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Ashland

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Ashland.

Weather in Ashland

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