A black clock with gold accents and the word "ASHLAND" on it.

Ashland Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Ashland holiday rentals

A narrow hallway with a wooden bench on the right, a rocking chair in the center, and a bed at the end.

1. The Katy Caboose in Hartsburg

The Katy Caboose in Hartsburg
Hartsburg
10.0 out of 10, Exceptional, (4 reviews)
"We had an amazing time on the trip! The host was amazing with communication and answering any questions that came up. The caboose itself was super comfortable and spacious. We really appreciated the pet friendly aspect and our dog had a wonderful time on the property!"
United States
Veronica R.
The price is HK$768
HK$1,554 total
includes taxes & fees
3 Nov - 4 Nov
The Katy Caboose in Hartsburg
A spacious living room with a brown sofa, wooden chairs, a coffee table, and a ceiling fan.

2. Quaint cottage w/ direct access to Katy Trail!

Quaint cottage w/ direct access to Katy Trail!
Hartsburg
10.0 out of 10, Exceptional, (2 reviews)
"They were so nice! Super clean, great place to stay!"
United States
Taylor R.
The price is HK$854
HK$1,654 total
includes taxes & fees
29 Nov - 30 Nov
Quaint cottage w/ direct access to Katy Trail!
A wooden pathway leading to a small cabin with a glass door and a crescent moon design.

3. Yurt Floating in the Forest

Yurt Floating in the Forest
Holts Summit
9.6 out of 10, Exceptional, (60 reviews)
"Great little getaway location!"
United States
Stephanie H.
The price is HK$981
HK$1,261 total
includes taxes & fees
3 Nov - 4 Nov
Yurt Floating in the Forest
A cozy bedroom with a bed, a wooden table, a chair, and a staircase.

4. Cozy cabin getaway with hot-tub under stars!

Cozy cabin getaway with hot-tub under stars!
Ashland
9.6 out of 10, Exceptional, (31 reviews)
"This is our second time staying here and we love it. Such a peaceful relaxing place."
United States
Ryan L.
The price is HK$1,236
HK$2,586 total
includes taxes & fees
5 Nov - 6 Nov
Cozy cabin getaway with hot-tub under stars!
A spacious living area with a sofa, a patterned ottoman, and a fireplace.

5. Whispering Woods Hideaway ~ Large Home ~ 85 in TV

Whispering Woods Hideaway ~ Large Home ~ 85 in TV
Columbia
9.8 out of 10, Exceptional, (6 reviews)
"Clean house. Very responsive"
United States
Gary B.
The price is HK$1,196
HK$3,620 total
includes taxes & fees
3 Nov - 4 Nov
Whispering Woods Hideaway ~ Large Home ~ 85 in TV
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

6. 3-bedroom Ranch Duplex in charming Columbia with WiFi, 6 miles to Mizzou Arena

3-bedroom Ranch Duplex in charming Columbia with WiFi, 6 miles to Mizzou Arena
Columbia
9.6 out of 10, Exceptional, (16 reviews)
"Great place to stay! "
United States
Stacy B.
The price is HK$1,045
HK$2,592 total
includes taxes & fees
4 Nov - 5 Nov
3-bedroom Ranch Duplex in charming Columbia with WiFi, 6 miles to Mizzou Arena
A covered patio with string lights, wicker furniture, and a ceiling fan.

7. Tranquil 3-bedroom house with AC in Holts Summit

Tranquil 3-bedroom house with AC in Holts Summit
Holts Summit
10.0 out of 10, Exceptional, (6 reviews)
"Great property in a convenient location"
United States
Camren B.
The price is HK$1,193
HK$1,621 total
includes taxes & fees
3 Nov - 4 Nov
Tranquil 3-bedroom house with AC in Holts Summit
A hallway with a blue-lit wall-mounted light fixture, a door leading to another room, and a wooden table in the foreground.

8. Como's Finest- A Home Away From Home- Sleeps 10

Como's Finest- A Home Away From Home- Sleeps 10
Columbia
9.4 out of 10, Exceptional, (8 reviews)
"Great place for a weekend trip"
United States
Brandon W.
The price is HK$753
HK$2,194 total
includes taxes & fees
3 Nov - 4 Nov
Como's Finest- A Home Away From Home- Sleeps 10
A kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

9. ~A Home Away From Home~Sleeps 8~

~A Home Away From Home~Sleeps 8~
Columbia
9.6 out of 10, Exceptional, (8 reviews)
"VRBO was exactly as described. Check in was super easy, and communication with the host was seamless."
United States
Bryon L.
The price is HK$709
HK$2,155 total
includes taxes & fees
3 Nov - 4 Nov
~A Home Away From Home~Sleeps 8~
An old brick building with a sign reading "Lupus General Store."

10. Quiet Riverfront Cottage on Missouri River

Quiet Riverfront Cottage on Missouri River
Jamestown
8.8 out of 10, Excellent, (17 reviews)
"It is a beautiful, quiet country setting and you can walk to the riverbank from the place."
United States
Patti M.
The price is HK$1,098
HK$1,502 total
includes taxes & fees
3 Dec - 4 Dec
Quiet Riverfront Cottage on Missouri River
A stone-walled entrance with a white door, a number '3' sign, and a small outdoor light fixture.

11. Super Close to Mizzou Condo 2 Bed 1 Bath

Super Close to Mizzou Condo 2 Bed 1 Bath
Columbia
10.0 out of 10, Exceptional, (19 reviews)
"The stay was great. Clean, quiet, comfortable, well equipped. Also very convenient location"
United States
William
The price is HK$392
HK$1,491 total
includes taxes & fees
8 Nov - 9 Nov
Super Close to Mizzou Condo 2 Bed 1 Bath
A two-story brick building with a sign reading "Lupus General Store".

12. Step Back in Time Near The Missouri River

Step Back in Time Near The Missouri River
Jamestown
9.8 out of 10, Exceptional, (24 reviews)
"Perfect spot!"
United States
Nicole
The price is HK$1,569
HK$2,271 total
includes taxes & fees
9 Nov - 10 Nov
Step Back in Time Near The Missouri River
A dining room with a wooden table and chairs, a potted plant, and a window with curtains.

13. Contractor/Family Hub-3 Living Areas - Sleeps Many

Contractor/Family Hub-3 Living Areas - Sleeps Many
Columbia
10.0 out of 10, Exceptional, (2 reviews)
"Host responded and communicated very quickly. Great value for a large group!"
United States
Brittany P.
The price is HK$1,550
HK$3,125 total
includes taxes & fees
4 Nov - 5 Nov
Contractor/Family Hub-3 Living Areas - Sleeps Many
A modern living room with a grey sofa set, a coffee table, and a fireplace. There are large windows providing natural light and a view of greenery outside.

14. Newly Built Home w/ Fresh Design!

Newly Built Home w/ Fresh Design!
Columbia
9.8 out of 10, Exceptional, (28 reviews)
"Great place!! Clean, new, and so nice!!"
United States
Eric
The price is HK$1,412
HK$2,508 total
includes taxes & fees
3 Nov - 4 Nov
Newly Built Home w/ Fresh Design!
Holiday Home Facilities and Services

15. 2 Double Beds Non-Smoking

2 Double Beds Non-Smoking
Fulton, MO
9.8 out of 10, Exceptional, (84 reviews)
"This place is great! They have a free breakfast buffet every morning in the lobby with steak and omelet bar, amazing value for the price!"
United States
Michael
The price is HK$526
HK$646 total
includes taxes & fees
1 Dec - 2 Dec
2 Double Beds Non-Smoking
A deck with a white railing, a metal staircase, and a view of trees and a building in the background.

16. Business or Pleasure - a perfect and cozy get-away!

Business or Pleasure - a perfect and cozy get-away!
Jefferson City
9.6 out of 10, Exceptional, (37 reviews)
"Comfortable overnight stay and convenient location!"
United States
Courtney B.
The price is HK$753
HK$1,494 total
includes taxes & fees
1 Dec - 2 Dec
Business or Pleasure - a perfect and cozy get-away!
An outdoor patio area with wicker furniture, a fire pit, and a covered seating area.

17. Near Mizzou | 1BR Suite w/ 2 Queen Beds & Kitchen

Near Mizzou | 1BR Suite w/ 2 Queen Beds & Kitchen
Columbia
8.0 out of 10, Very good, (2 reviews)
"Nice rooms at a reasonable price"
United States
Butch D.
The price is HK$1,278
HK$1,553 total
includes taxes & fees
8 Nov - 9 Nov
Near Mizzou | 1BR Suite w/ 2 Queen Beds & Kitchen
EXTERIOR

18. PREMIUM STAY NEAR THE CAPITOL AND DOWNTOWN

PREMIUM STAY NEAR THE CAPITOL AND DOWNTOWN
Jefferson City
The price is HK$753
HK$1,184 total
includes taxes & fees
12 Nov - 13 Nov
PREMIUM STAY NEAR THE CAPITOL AND DOWNTOWN
A modern living room with a dining area, a flat-screen TV mounted on the wall, and a door leading to another room.

19. Jefferson City Bungalow: Hot Tub & Patio!

Jefferson City Bungalow: Hot Tub & Patio!
Jefferson City
9.0 out of 10, Wonderful, (9 reviews)
"Clean and perfect location. Hot tub and message chair were great! "
United States
Heather I.
The price is HK$659
HK$2,106 total
includes taxes & fees
5 Nov - 6 Nov
Jefferson City Bungalow: Hot Tub & Patio!
Interior

20. Cozy Capital House - Downtown JC - Perfect for Families & Work Trips

Cozy Capital House - Downtown JC - Perfect for Families & Work Trips
Jefferson City
8.6 out of 10, Excellent, (7 reviews)
"A very clean economical place to stay. a super attentive host, very friendly, very central, which is also useful. We enjoyed our company trip. Charming large folder with complete information about local restaurants and attractions, information about the lake, everything. I would definitely be in contact if we ever visit the area again. Thanks again for hosting us!"
United States
Kirk M.
The price is HK$887
HK$1,865 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Capital House - Downtown JC - Perfect for Families & Work Trips
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Country Inn & Suites by Radisson, Columbia, MO

Country Inn & Suites by Radisson, Columbia, MO

10/10 Excellent
"Clean property, good location."
Carrie 3-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Columbia, MO

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:

  • View our selection of featured holiday rentals in Ashland
  • Use the map to find apartments and other holiday homes in the Ashland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

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?

Quiet 3 min to campus! Back porch/decks & firepit, w/ 5 car parking. YourPlace!: This holiday home rental outside of Ashland offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 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?

Explore the area and family-friendly sights such as Midway Golf and Games, or get out into nature at a spot like Shelter Gardens. In the wider area, you’ll find Rock Bridge Memorial State Park and Mizzou Arena.

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 your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.