A deer on a road with vegetation on the sides.

Ashland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ashland vacation rentals

Sundeck

1. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
$403 nightly
The price is $409
Sep 13 - Sep 14
Total with taxes and fees
Grandview of Ashland
Interior

2. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
$377 nightly
The price is $420
Sep 11 - Sep 12
Total with taxes and fees
Savage Upon Siskiyou
Rosebud | Terrace/patio

3. A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (52 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
$273 nightly
The price is $304
Sep 14 - Sep 15
Total with taxes and fees
A Cowslip's Belle Inn
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

4. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
$271 nightly
The price is $302
Sep 14 - Sep 15
Total with taxes and fees
Barclay Klum House by WanderLodges
Grand House | Living area | 65-inch TV with digital channels, streaming services

5. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
$345 nightly
The price is $385
Sep 12 - Sep 13
Total with taxes and fees
The Mountain Ave House by WanderLodges
Interior detail

6. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
$308 nightly
The price is $343
Sep 27 - Sep 28
Total with taxes and fees
Hanna's House by WanderLodges
House | Private kitchen | Full-size fridge, microwave, oven, stovetop

7. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
$400 nightly
The price is $406
Sep 13 - Sep 14
Total with taxes and fees
Paschal Winery
Family Villa, Multiple Bedrooms, Valley View | Outdoor dining

8. Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
Meadowsweet Farm by WanderLodges
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels

9. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
$163 nightly
The price is $183
Sep 11 - Sep 12
Total with taxes and fees
Rosewood Studio by WanderLodges
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels

10. The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (6 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
$403 nightly
The price is $409
Sep 13 - Sep 14
Total with taxes and fees
The Rellik House and Winery
Toys

11. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
$492 nightly
The price is $554
Sep 14 - Sep 15
Total with taxes and fees
Rosewood Collective- House & Studio
View from property

12. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very Good, (481 reviews)
"Great location."
United States
Noni
$89 nightly
The price is $97
Sep 11 - Sep 12
Total with taxes and fees
Rocky Point Resort
Premium House, 3 Bedrooms, Pets Allowed | Living area | Flat-screen TV

13. Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
$262 nightly
The price is $295
Sep 22 - Sep 23
Total with taxes and fees
Starwood Sanctuary
House (0 Bedroom) | Interior

14. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
$195 nightly
The price is $213
Sep 11 - Sep 12
Total with taxes and fees
Forest Cabin by Crater Lake & Klamath Falls
Flat-screen TV, fireplace

15. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
$404 nightly
The price is $455
Sep 14 - Sep 15
Total with taxes and fees
Rosewood Landing- Hot Tub- Sauna
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Best Western Windsor Inn

Best Western Windsor Inn

10/10 Excellent
"I would stay here again,"
Bethel 1-night trip
Posted 5 hours ago
Best Western Windsor Inn

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $97 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!: This highly rated vacation home rental in Ashland has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Gorgeous Lakeside BarnHOUSE + SAUNA!.

How many vacation rentals are there in Ashland?

Choose from 108 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.