Ashland Vacation 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
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Ashland vacation rentals

1 bedroom, desk, free WiFi, wheelchair access

Spacious Suite in Hotel

Spacious Suite in Hotel
McAlester
10.0 out of 10, Exceptional, (5 reviews)
"Very nice people and room, pet friendly and clean."
United States
Martin B.
The price is ￥9,349
￥15,348 total
includes taxes & fees
Apr 4 - Apr 5
Spacious Suite in Hotel
Outdoor dining

Spacious King Suite in Hotel

Spacious King Suite in Hotel
McAlester
8.0 out of 10, Very Good, (1 review)
"Fairly clean but killed a couple of roaches"
United States
Albert M.
The price is ￥9,349
￥13,574 total
includes taxes & fees
Apr 4 - Apr 5
Spacious King Suite in Hotel
Property grounds

Lovely secluded cabin #1

Lovely secluded cabin #1
Allen
10.0 out of 10, Exceptional, (64 reviews)
"The winery owners were very friendly. The cabin was cozy and very clean. We will definitely be going back. "
United States
Luisa T.
The price is ￥18,698
￥22,923 total
includes taxes & fees
Apr 4 - Apr 5
Lovely secluded cabin #1
Dining

Lovely secluded rustic cabin within waking distance of Rocky Top Winery .

Lovely secluded rustic cabin within waking distance of Rocky Top Winery .
Atwood
10.0 out of 10, Exceptional, (104 reviews)
"Quiet, clean, comfy and relaxing. Owners are friendly and wine is good"
United States
Dawn A.
The price is ￥18,698
￥28,924 total
includes taxes & fees
Apr 4 - Apr 5
Lovely secluded rustic cabin within waking distance of Rocky Top Winery .
Property grounds

Rocky Top Winery Cabin #2

Rocky Top Winery Cabin #2
Allen
9.8 out of 10, Exceptional, (39 reviews)
"The cabin was cozy, and clean. The cabin was beautiful inside and the porch area was a wonderful sitting area with a view. The owners were kind and pleasant to talk with when we went to visit the winery. We had no issues getting into our cabin for our stay."
United States
Leona
The price is ￥20,775
￥25,114 total
includes taxes & fees
Apr 4 - Apr 5
Rocky Top Winery Cabin #2
Outdoor dining

Beautiful cozy rustic cedar cabin located close to Rocky Top Winery.

Beautiful cozy rustic cedar cabin located close to Rocky Top Winery.
Allen
10.0 out of 10, Exceptional, (33 reviews)
"Cabin was clean and spacious. Great views on the porches."
United States
steve
The price is ￥22,293
￥26,717 total
includes taxes & fees
Apr 4 - Apr 5
Beautiful cozy rustic cedar cabin located close to Rocky Top Winery.
Free WiFi, bed sheets

Rocky Top Winery Beautiful Rustic Cedar Cabin

Rocky Top Winery Beautiful Rustic Cedar Cabin
Allen
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean place to stay with a great view of the lake"
United States
Randall P.
The price is ￥18,756
￥22,995 total
includes taxes & fees
Apr 2 - Apr 3
Rocky Top Winery Beautiful Rustic Cedar Cabin
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

Candlelight Inn & Suites Hwy 69 near McAlester

Candlelight Inn & Suites Hwy 69 near McAlester

10/10 Excellent
"Everything was wonderful! "
Judy 1-night trip
Posted 1 day ago
Candlelight Inn & Suites Hwy 69 near McAlester

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 vacation rental in Ashland?

Yes, we have vacation rentals near the most popular attractions in Ashland, or you can go with a secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Ashland has to offer?

Cozy Ranch Home w/Spacious living/ kitchen, screened in porch : You might want to consider this vacation home rental near Ashland, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Ashland?

While you're exploring the area, Drew Park and Kiowa City Park are a couple of picturesque spots to get outside and enjoy nature.

What’s a vacation rental in Ashland like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Ashland. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips or small group gatherings.