Search Holiday Rentals in Ashland

May 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

June 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
This weekend
2 May - 4 May
Next weekend
9 May - 11 May

Top Holiday Rentals in Ashland

A Cowslip's Belle Inn
Main House | Terrace/patio

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (31)
"Lovely place and the room had everything I needed. "
The price is Rp3.584.776
Rp4.921.194 total
includes taxes & fees
19 May - 20 May
A Cowslip's Belle Inn
Barclay Klum House by WanderLodges
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (4)
"One can truly enjoy family time & dinners ~ kitchen is beautifully equipped ⚜️❄️~ Dining room ~ gorgeous ~ open concept makes space perfect 👍 "
The price is Rp2.372.169
Rp4.781.312 total
includes taxes & fees
5 May - 6 May
Barclay Klum House by WanderLodges
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 Rp4.969.494
Rp8.596.508 total
includes taxes & fees
4 May - 5 May
Grandview of Ashland
Rocky Point Resort
Kayaking

Rocky Point Resort

2.5 star property
8.2 out of 10, Very good, (349)
"Enjoyed my one night stay. Very calming beautiful views and a friendly staff. Feels like you’re part of the family "
The price is Rp1.626.204
Rp1.845.683 total
includes taxes & fees
16 May - 17 May
Rocky Point Resort
Paschal Winery
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (9)
"If I could add a sixth or even a seventh star for comfort.... I would. That you Rory for an amazing stay. "
The price is Rp2.894.344
Rp4.512.574 total
includes taxes & fees
4 May - 5 May
Paschal Winery
Peach Street Inn by WanderLodges
Suite 1, King Bed | Private kitchen | Fridge, microwave, oven, stovetop

Peach Street Inn by WanderLodges

2.0 star property
9.2 out of 10, Wonderful, (5)
"The Peach Tree Inn was newly remodeled and very clean. Heather's communication was great! "
The price is Rp1.457.284
Rp2.826.245 total
includes taxes & fees
4 May - 5 May
Peach Street Inn by WanderLodges
Medford Home and 2 Condos With Pool and Hot tub
Apartment | 6 bedrooms

Medford Home and 2 Condos With Pool and Hot tub

2.0 star property
The price is Rp1.269.135
Rp4.726.494 total
includes taxes & fees
5 May - 6 May
Medford Home and 2 Condos With Pool and Hot tub
The Rellik House and Winery
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
The price is Rp2.894.344
Rp6.087.389 total
includes taxes & fees
1 Jun - 2 Jun
The Rellik House and Winery
Enchanting Getaway: Farmhouse and Tiny House Duo
House | 4 bedrooms

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is Rp1.643.779
Rp3.542.514 total
includes taxes & fees
14 May - 15 May
Enchanting Getaway: Farmhouse and Tiny House Duo
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Ashland you may be interested in

Ashland Hills Hotel & Suites
Lobby sitting area

Ashland Hills Hotel & Suites

3.0 star property
9.0 out of 10, Wonderful, (1433)
"The room and grounds were beautiful. Everything was comfortable and easy to access. Highly recommend"
The price is Rp1.924.590
Rp2.311.663 total
includes taxes & fees
18 May - 19 May
Ashland Hills Hotel & Suites
Stratford Inn
Exterior detail

Stratford Inn

2.5 star property
9.2 out of 10, Wonderful, (1544)
"It was great but where were the cookies baked every evening? 😊"
The price is Rp1.574.815
Rp1.755.919 total
includes taxes & fees
4 May - 5 May
Stratford Inn
Ashland Springs Hotel
Garden

Ashland Springs Hotel

3.0 star property
9.4 out of 10, Exceptional, (1001)
"Wonderful "
The price is Rp2.571.424
Rp2.950.023 total
includes taxes & fees
5 May - 6 May
Ashland Springs Hotel
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.

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.

How many holiday rentals are there in Ashland?

Choose from 125 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 Mount Ashland Ski Area 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.