Ashland Holiday Rentals

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Check prices for these dates

Tonight
29 Jul - 30 Jul
Tomorrow
30 Jul - 31 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Ashland

A Cowslip's Belle Inn
Terrace/patio

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (34)
"What a wonderful place to stay! The owners were very cordial and offered suggestion about places to go. We particularly loved to Koi pond right off our deck. "
The price is S$351
includes taxes & fees
5 Aug - 6 Aug
A Cowslip's Belle Inn
Barclay Klum House by WanderLodges
Private kitchen

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"Great ~ memorable stay. "
The price is S$397
includes taxes & fees
19 Aug - 20 Aug
Barclay Klum House by WanderLodges
Hanna's House by WanderLodges
Private kitchen

Hanna's House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (1)
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once and walked everywhere. Lovely host. Really, I can't imagine anyone giving it less than a perfect score. Would definitely stay here again."
The price is S$279
includes taxes & fees
19 Aug - 20 Aug
Hanna's House by WanderLodges
232 4th Street
Lounge

232 4th Street

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location with easy access to downtown Ashland. We were able to walk nearly everywhere we wanted to go and enjoyed the neighborhood shops. Overall the neighborhood was quiet and the accommodations were what we wanted. "
232 4th Street
Hiking Trail On-site: Mtn-view Eagle Point Retreat
Interior

Hiking Trail On-site: Mtn-view Eagle Point Retreat

3.0 star property
10.0 out of 10, Exceptional, (2)
"Very cute and cozy place to stay in the country. We met a bunch of wild turkey and deer in trip back and forth to home. The place was clean, inviting and privare. Enjoyed our stay!"
Hiking Trail On-site: Mtn-view Eagle Point Retreat
Grandview of Ashland
Terrace/patio

Grandview of Ashland

3.0 star property
10.0 out of 10, Exceptional, (1)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
The price is S$620
includes taxes & fees
19 Aug - 20 Aug
Grandview of Ashland
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
Living area

Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

3.5 star property
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
Whispering Pines Cabin Retreat
Private kitchen

Whispering Pines Cabin Retreat

3.5 star property
Whispering Pines Cabin Retreat
Ashland Lodge w/ Lake Views & Game Room Loft
Front of property

Ashland Lodge w/ Lake Views & Game Room Loft

3.0 star property
Ashland Lodge w/ Lake Views & Game Room Loft
Peach Street Inn by WanderLodges
Private kitchen

Peach Street Inn by WanderLodges

2.0 star property
9.0 out of 10, Wonderful, (17)
"Great space to relax, bed was comfy, property was clean and quiet. Awesome spot, would definitely stay again."
Peach Street Inn by WanderLodges
Paschal Winery
Living area

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
The price is S$323
includes taxes & fees
7 Aug - 8 Aug
Paschal Winery
Rocky Point Resort
Sun deck

Rocky Point Resort

2.5 star property
8.2 out of 10, Very good, (361)
"Great stay!"
Rocky Point Resort
The Rellik House and Winery
Living area

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
The price is S$473
includes taxes & fees
28 Aug - 29 Aug
The Rellik House and Winery
Enchanting Getaway: Farmhouse and Tiny House Duo
Room

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is S$269
includes taxes & fees
11 Aug - 12 Aug
Enchanting Getaway: Farmhouse and Tiny House Duo
Remote Escape: Klamath Falls Cabin By Lake & Hikes
Interior

Remote Escape: Klamath Falls Cabin By Lake & Hikes

2.0 star property
10.0 out of 10, Exceptional, (1)
"The cabin was amazing! Very cool log cabin vibe with all of the decorations to make you feel like you're roughing it in the woods but with all the modern convenience to make it comfortable. The outdoor bathtub and grilling area were standouts. The cabin actually does have AC even though the listing says it doesn't so that was a relief for a summer getaway. We came to see Crater Lake and it was close enough to recommend it for anyone wanting to see crater along with lake activities closer by at...
Remote Escape: Klamath Falls Cabin By Lake & Hikes
Medford Home and 2 Condos With Pool and Hot tub
Room

Medford Home and 2 Condos With Pool and Hot tub

2.0 star property
The price is S$415
includes taxes & fees
5 Aug - 6 Aug
Medford Home and 2 Condos With Pool and Hot tub
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
"The room was clean ans comfortable. The mini fridge-freezer combo makes it easy to bring food. It is in walking distance of the Shakespeare festival and the indoor pool delighted my kids "
Reyna 1-night trip
Posted 8 hours ago
Stratford Inn

Frequently asked questions

Can I find holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to ScienceWorks Hands-On Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Ashland like the picturesque gardens and renowned opera 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 holiday rentals that Ashland has to offer?

Barclay Klum House by WanderLodges: This highly rated holiday home rental in Ashland is located near the airport, and has a private garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. Our travellers also rate Hanna's House by WanderLodges as a favourite home for rent in Ashland.

How many holiday rentals are there in Ashland?

Choose from 130 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

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

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.