Ashland Holiday Rentals: Short-Term Accommodations for Rent

Q: 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 is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Holiday Rentals in Ashland

Convenient self-service laundry area with industrial-style washing machines and additional amenities.

Kitchen area with a central island, stainless steel appliances, and a light-colored countertop.

"Great location. Close to downtown, restaurants, and the state fair and pet friendly too."

HK$1,904 total

includes taxes & fees

25 Jul - 26 Jul

Enjoy cooking in this kitchen with utensil storage, coffee maker, and toaster.

"Host was easy to work with and property was nice! "

HK$1,994 total

includes taxes & fees

4 Aug - 5 Aug

Modern kitchen with central island, appliances, and dining area for four.

"Adorable, nicely decorated and had everything we needed. We were very comfortable staying in this little country house. Location was perfect. Owner was friendly & responsive. Honestly, the cleanest VRBO we have ever been in."

Stunning two-story home with a charming red front door and lush green surroundings.

"Lots of room for my multi-generational family of 7! Our host was super-responsive and helpful."

Stunning interior with a grand staircase, plush armchairs, and a large mirror.

"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!"

Stroll up to this charming two-story home, featuring a spacious front porch and balcony, perfect for taking in the surroundings.

"Wayne was a great host and his property is in a great location and neighborhood. Would definitely look to stay again if we’re back in the area!"

Stroll up to the charming front porch and enter through the small entryway door.

"Quiet tranquill neighborhood. It was a very relaxing getaway! "

HK$1,928 total

includes taxes & fees

13 Aug - 14 Aug

Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, microwave, stove, and refrigerator.

"We had an overnight here and it was just what we needed!"

Cozy room with a dining table, desk, and large window, perfect for a relaxing stay.

"Beautiful place to stay. Aubrey was an excellent host."

Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and ample countertop space.

"This home was beautiful! Absolutely stunning and completely clean. There was nothing out of place and everhything in the description was true with no exaggeration. The owner was very responsive and compassionate...beyond words! This was probably the best stay I've experienced. "

Enjoy cooking in this kitchen with an oven, stainless steel appliances, and a large window overlooking the backyard.

"Fine location and house"

Relax in a charming outdoor space surrounded by trees and a wooden fence.

Cozy retreat with a large bed, potted plant, and framed artwork.

"Perfect place to stay with little ones. They have a toy box and room to play. Had a good stay."

Relax in this inviting living room with a television, bookshelf, and window with a decorative door.

"This would be a great place for an extended stay! Great people and the place was very comfortable!"

HK$1,104 total

includes taxes & fees

28 Jul - 29 Jul

Relax in style with a sofa, armchairs, and a small table on this outdoor patio, complete with a fire pit and lush greenery.

"Perfect spot for our stay"

Steps lead up to the entrance of this charming building, flanked by double doors and surrounded by lush potted plants.

"Clean and great location"

Cozy cabin interior with a dining table, leather sofa, and decorative cabinet.

"Everything was great. The fishing pond was an unexpected bonus for the kids. The latches on both bathrooms didn’t lock."

Spacious kitchen with exposed brick walls, wooden cabinetry, and a large island with a sink.

"This place was amazing, lots of amenities and the town of Petersburg is very charming. "

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and refrigerator.

"Enjoyed our stay as part of a family road trip."

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Top Ashland Hotel Reviews

Best Western Jacksonville Inn

10/10 Excellent

"Very nice room. Was able to park right outside our room. Very close to lots of food options."

Villa DeWolf

10/10 Excellent

"The owner communicated early and often to make sure we were good upon arrival. The house is beautiful and well appointed. The rooms are upstairs but the butler Kimo will bring up your luggage. The room was spacious and bathroom had everything needed - even 2 robes!! Breakfast was amazing - home cooked and very filling. I'm a vegetarian and he accommodated me easily. Would stay there again. "

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

10/10 Excellent

"Three Pines is an amazing place! We hosted our wedding here in June of 2025 and could not have asked for a more beautiful setting, attentive staff, and quiet grounds. We had guests in every rentable room, and they all raved about the accommodations. It was especially hot outside during our stay and the house was a very comfortable temperature with the ability to adjust certain rooms to be warmer or cooler to your needs, which was especially pleasing given the historic nature of the home. You will not be disappointed renting the entire house for an event or a single room for yourself. We loved everything about Three Pines and will be back to celebrate anniversaries and events for years to come!"

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ashland!

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 is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Ashland?

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

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.

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Ashland Holiday Rentals

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Holiday Rentals in Ashland

Hunters Delight

Modern Bungalow Home with Mid-Century Flair

Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

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

Historic Bungalow: For Groups & Families Sleeps 11

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

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

Newly-renovated 2-bedroom House with a Luxurious Massage Chair

COZY BUNGALO

Holly & Matt Suite @ Three Pines Petersburg

Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village

The Archer Home

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

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

Very Cozy and Secluded. Completely remodeled beautiful back apartment

Pet friendly remodeled bungalow home just two blocks from Washington Park.

Style on the Square 2-bedroom bungalow with WiFi, AC in Petersburg

Charming 4-bedroom house with AC and WiFi in Springfield just outside city limit

The Loft on the Square

Spacious & Cozy ~ Mins to Downtown

Top Ashland Hotel Reviews

Best Western Jacksonville Inn

Sleep Inn Springfield West

Hampton Inn Jacksonville

Villa DeWolf

Spark by Hilton Springfield Southwest

Quality Inn and Suites Springfield Southwest near I-72

Courtyard by Marriott Springfield

Sleep Inn & Suites

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Find out more about Ashland

Frequently asked questions