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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Ashland vacation rentals

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
$250 nightly
The price is $279
Sep 29 - Sep 30
Total with taxes and fees
Barclay Klum House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

2. 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
$258 nightly
The price is $287
Oct 4 - Oct 5
Total with taxes and fees
Hanna's House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

3. 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
$366 nightly
The price is $408
Sep 28 - Sep 29
Total with taxes and fees
Savage Upon Siskiyou
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

4. 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
$339 nightly
The price is $378
Oct 4 - Oct 5
Total with taxes and fees
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

5. 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
$498 nightly
The price is $505
Oct 4 - Oct 5
Total with taxes and fees
Grandview of Ashland
A spacious kitchen with a central island, bar stools, and a fireplace.

6. 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
$395 nightly
The price is $401
Sep 28 - Sep 29
Total with taxes and fees
Paschal Winery
An outdoor patio with a stone fireplace, wooden seating, and a view of the surrounding landscape.

7. Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
$598 nightly
The price is $607
Sep 28 - Sep 29
Total with taxes and fees
Meadowsweet Farm by WanderLodges
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

8. 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
$254 nightly
The price is $286
Sep 29 - Sep 30
Total with taxes and fees
Starwood Sanctuary
A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

9. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
$164 nightly
The price is $185
Sep 28 - Sep 29
Total with taxes and fees
Rosewood Studio by WanderLodges
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

10. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
$468 nightly
The price is $527
Sep 29 - Sep 30
Total with taxes and fees
Rosewood Collective- House & Studio
A clear view of a lake with a mountain in the background, a dock, and a chair on a deck.

11. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (496 reviews)
"Restaurant yummy and people were great."
United States
Jennifer
$99 nightly
The price is $108
Sep 28 - Sep 29
Total with taxes and fees
Rocky Point Resort
A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

12. 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 28 - Sep 29
Total with taxes and fees
The Rellik House and Winery
A signpost with the word "Canowinga" indicating a location.

13. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
$205 nightly
The price is $224
Oct 4 - Oct 5
Total with taxes and fees
Forest Cabin by Crater Lake & Klamath Falls
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

14. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
$347 nightly
The price is $391
Sep 29 - Sep 30
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.
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Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"We have a spacious, clean and modern room with kitchen. The hotel is walkable to downtown. There is a good breakfast. I will stay again."
Anna 1-night trip
Posted 1 hour ago
Stratford 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 $275 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?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated vacation home rental in Ashland is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!.

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.