Ashland Holiday Rentals

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Holiday Rentals in Ashland

Hunters Delight

Hunters Delight

Modern Bungalow Home with Mid-Century Flair

9.6 out of 10, Exceptional, (20)
"Home was nice and clean. Host responds quickly. For fur parents there’s not many places to walk your dogs but there are dog parks near by. The back yard is large and secure enough for dogs to roam. The grass wasn’t mowed in the back other than that no other issues. "
The price is AU$275
includes taxes & fees
9 Dec - 10 Dec
Modern Bungalow Home with Mid-Century Flair

COZY BUNGALO

9.4 out of 10, Exceptional, (63)
"Was well equipped, comfy,convenient to sites.Only suggestions more writing utensils "
COZY BUNGALO

Completely remodeled, pet-friendly, 'smart' home in the country!

9.8 out of 10, Exceptional, (62)
"This was a perfect location, out in the country but still 15-20min from everything we needed. The house was very clean, beautifully done and dog friendly (but you couldn’t tell by walking in). The host got back to us right away when we asked questions. 100% will stay here again "
Completely remodeled, pet-friendly, 'smart' home in the country!

Lower duplex apartment, centrally located. Beautifully furnished, 1970s feel.

10.0 out of 10, Exceptional, (77)
" !"
The price is AU$226
includes taxes & fees
26 Nov - 27 Nov
Lower duplex apartment, centrally located. Beautifully furnished, 1970s feel.

Tranquil 2-bedroom house with a massage chair and a multi-purpose room

2.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! The kids really spent time with there dad"
The price is AU$404
includes taxes & fees
26 Nov - 27 Nov
Tranquil 2-bedroom house with a massage chair and a multi-purpose room

Historic Bungalow: For Groups & Families Sleeps 11

10.0 out of 10, Exceptional, (1)
"Overall a nice property for what our family was looking for. Plus it was located in a great location. "
Historic Bungalow: For Groups & Families Sleeps 11

Very Cozy and Secluded. Completely remodeled beautiful back apartment

10.0 out of 10, Exceptional, (52)
"Another quiet and peaceful stay at this special property. Elana and Justin are the best hosts and the dogs are super sweet and friendly. Very special and highly recommended "
The price is AU$235
includes taxes & fees
10 Dec - 11 Dec
Very Cozy and Secluded. Completely remodeled beautiful back apartment

Home with great location

10.0 out of 10, Exceptional, (15)
"Such a wonderful home. The decor is charming. Great location"
Home with great location

Holly & Matt Suite @ Three Pines Petersburg

10.0 out of 10, Exceptional, (20)
"Beautiful place to stay. Aubrey was an excellent host."
Holly & Matt Suite @ Three Pines Petersburg

Modern Like New LUXURY 3,200 SQ FT Home In An Awesome Location! Sleeps 12!

9.8 out of 10, Exceptional, (96)
"This house was perfect for our stay! Everything was very clean. The beds were extremely comfortable. I would absolutely recommend this property and I would stay here again."
Modern Like New LUXURY 3,200 SQ FT Home In An Awesome Location! Sleeps 12!

The Loft on the Square

9.8 out of 10, Exceptional, (76)
"Very nice loft, enjoyed the atmosphere of the town and people. We felt safe and were very comfortable. Great break for us. Would recommend."
The Loft on the Square

Charming barn-turned-home with hot tub & W/D - quiet location & dog-friendly

Charming barn-turned-home with hot tub & W/D - quiet location & dog-friendly

Spacious & Cozy ~ Mins to Downtown

8.0 out of 10, Very good, (13)
"Pros: Beds were comfortable with bedside tables and access to outlets, carpeting looked new. Great location to local attractions and restaurants. Felt like a safe neighborhood. Driveway fits two cars, with street parking available for more. Owner very responsive to questions. Cons: Needs better attention to cleaning (windowsills were very dirty throughout, air exchange vents were either super dirty or rusted); Could use a table and/or luggage racks in bedrooms. Upstairs bathroom had a walk-in...
Spacious & Cozy ~ Mins to Downtown

20% OFF Solid Luxury Living(WIFI+PARKING)

4.8 out of 10, (3)
"We never received instructions on how to enter the house. When we tried to contact the owner, they didn't respond to messages. The phone number listed on the app, was an incorrect phone number. There's nothing good to say about this experience!"
20% OFF Solid Luxury Living(WIFI+PARKING)

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

9.8 out of 10, Exceptional, (19)
"Tons of character, wonderfully taken care of, great hosts, Aubrey is super easy to work with and very accommodating. Loved the flexibility to host our wedding in a unique way that fit us!"
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Remodeled bungalow home just two blocks from Washington Park.

10.0 out of 10, Exceptional, (4)
"Perfect place for our long weekend visit. Great location to where we had to go."
Remodeled bungalow home just two blocks from Washington Park.

Rainbow Retreat ~ 3-bedroom fun loving home full of color!

9.6 out of 10, Exceptional, (4)
"This home is very nice and cozy. It was centrally located to so many things we wanted to see in Springfield. The property manager/owner was so nice, and communicated with us frequently and promptly. The guide they put together for the house and surrounding areas was the nicest I have seen for any vacation rental house!"
Rainbow Retreat ~ 3-bedroom fun loving home full of color!

Downtown Med District: Idyllic 2BD, 1BA Capital City Retreat

10.0 out of 10, Exceptional, (1)
Downtown Med District: Idyllic 2BD, 1BA Capital City Retreat

Capital City Retreat: Idyllic 2BD, 1BA Gem in Springfield Medical District!

10.0 out of 10, Exceptional, (3)
"The property was in a great location and it was very nice and cozy! The rooms was spacious, very clean, and was suitable for our needs! The host was very pleasant, very responsive, and very detailed on directions and instructions regarding where to park, how to get to the property, how to get into the property and if we had any questions or concerns to let them know immediately! The host also sent us a guide book for the city! It was very thoughtful and well appreciated. Also, this location is...
Capital City Retreat: Idyllic 2BD, 1BA Gem in Springfield Medical District!
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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Other types of properties in Ashland you may be interested in

Hunters Delight

Hunters Delight

Sleep Inn Springfield West

2.5 star property
8.8 out of 10, Excellent, (118)
"It was a calm atmosphere. The staff is friendly and attentive. The room exceeded my expectations. "
The price is AU$87
includes taxes & fees
8 Dec - 9 Dec
Sleep Inn Springfield West

Quality Inn and Suites Springfield Southwest near I-72

2.5 star property
7.8 out of 10, Good, (599)
"Staff was excellent, liked all the tiny things to minimize environmental impact, no excess plastic usage."
The price is AU$97
includes taxes & fees
8 Dec - 9 Dec
Quality Inn and Suites Springfield Southwest near I-72
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Ashland?

Yes, there are holiday rentals close to the most popular sights in Ashland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Modern Bungalow Home with Mid-Century Flair: This holiday home rental outside of Ashland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Ashland?

While exploring the area, visit the sights like Lincoln's New Salem State Historic Site, Woodlawn Farm and Shambolee Golf Course. In the wider area, you’ll find Mt. Bike Trailhead and Panther Creek State Fish and Wildlife Area.

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 amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.