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Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

1. The Cabins at Healing Springs

The Cabins at Healing Springs
2.0 star property
Crumpler
9.0 out of 10, Wonderful, (169 reviews)
"Would have liked to have talked to someone at some at some point. I always ask about places to see, points of interest, local hikes, etc. Also, an ice machine in the office would be a great addition. We enjoyed our stay. Very quiet and relaxing."
United States
David
The price is CA $122
CA $189 total
includes taxes & fees
Nov 9 - Nov 10
The Cabins at Healing Springs

2. Downtown Mountain City

Downtown Mountain City
Mountain City
9.6 out of 10, Exceptional, (209 reviews)
"Great place, this was our fourth stay there and highly recommend it. Very affordable and pet friendly. "
United States
Scott V.
The price is CA $109
CA $230 total
includes taxes & fees
Dec 2 - Dec 3
Downtown Mountain City

3. New 3br Home 20 mins to Boone | Loft + Fireplace

New 3br Home 20 mins to Boone | Loft + Fireplace
Trade
The price is CA $161
CA $477 total
includes taxes & fees
Nov 9 - Nov 10
New 3br Home 20 mins to Boone | Loft + Fireplace

4. Cozy , comfortable, and warm with unique features and plenty of amenities!

Cozy , comfortable, and warm with unique features and plenty of amenities!
Mountain City
9.8 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay"
United States
Luella K.
The price is CA $143
CA $279 total
includes taxes & fees
Dec 1 - Dec 2
Cozy , comfortable, and warm with unique features and plenty of amenities!

5. Newly renovated cottage, 5 min walk to town, dogs OK, fire pit, hot tub, wi-fi

Newly renovated cottage, 5 min walk to town, dogs OK, fire pit, hot tub, wi-fi
West Jefferson
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful stay and great location! "
United States
Jazmin S.
The price is CA $132
CA $352 total
includes taxes & fees
Nov 8 - Nov 9
Newly renovated cottage, 5 min walk to town, dogs OK, fire pit, hot tub, wi-fi

6. Laurel Hill Haven: Glamping in SW Virginia

Laurel Hill Haven: Glamping in SW Virginia
Mouth of Wilson
9.4 out of 10, Exceptional, (11 reviews)
"Had a wonderful stay. Was pleasantly surprised to find the property was very private with no houses or other people around. The pictures of the property don't quite do this spot justice. Loved that you could also hear the nearby creek as well. I'll be back for sure."
United States
Jeremiah
The price is CA $111
CA $185 total
includes taxes & fees
Nov 8 - Nov 9
Laurel Hill Haven: Glamping in SW Virginia

7. Modern Log Cabin TH Retreat | Peaceful | Mountain Views | Steps to Downtown WJ

Modern Log Cabin TH Retreat | Peaceful | Mountain Views | Steps to Downtown WJ
Downtown West Jefferson
10.0 out of 10, Exceptional, (25 reviews)
"Great location for our 2 day getaway."
United States
Carrie C.
The price is CA $155
CA $558 total
includes taxes & fees
Nov 8 - Nov 9
Modern Log Cabin TH Retreat | Peaceful | Mountain Views | Steps to Downtown WJ

8. OMG!!! Cozy Log GUEST CABIN on Horse Ranch w Mountain Views. Pet Friendly!

OMG!!! Cozy Log GUEST CABIN on Horse Ranch w Mountain Views. Pet Friendly!
Boone
9.4 out of 10, Exceptional, (50 reviews)
"Had a great stay!"
United States
Christopher P.
The price is CA $156
CA $380 total
includes taxes & fees
Nov 8 - Nov 9
OMG!!! Cozy Log GUEST CABIN on Horse Ranch w Mountain Views. Pet Friendly!

9. 2 King Suites | Mtn Views | Walk Downtown

2 King Suites | Mtn Views | Walk Downtown
West Jefferson
9.6 out of 10, Exceptional, (8 reviews)
"Good communication, the place was just right for us. Location was great."
United States
Karen G.
The price is CA $155
CA $558 total
includes taxes & fees
Nov 8 - Nov 9
2 King Suites | Mtn Views | Walk Downtown

10. A View for Two: Tiny House with BIG VIEWS

A View for Two: Tiny House with BIG VIEWS
Fleetwood
9.8 out of 10, Exceptional, (156 reviews)
"Place was great for what was needed! David was an amazing host and answered every question/concern we had. The views were to die for! Will definitely be back another time!"
United States
Kayce S.
The price is CA $82
CA $178 total
includes taxes & fees
Nov 8 - Nov 9
A View for Two: Tiny House with BIG VIEWS

11. Rustic Log Cabin TH | Spacious King Suite | Views | Fire Pit | Walk Downtown WJ

Rustic Log Cabin TH | Spacious King Suite | Views | Fire Pit | Walk Downtown WJ
West Jefferson
10.0 out of 10, Exceptional, (24 reviews)
"Great place and so close to downtown. I would definitely stay there again! "
United States
David M.
The price is CA $155
CA $558 total
includes taxes & fees
Nov 8 - Nov 9
Rustic Log Cabin TH | Spacious King Suite | Views | Fire Pit | Walk Downtown WJ

12. {Riverbend Retreat} – Cozy Cabin

{Riverbend Retreat} – Cozy Cabin
Fleetwood
8.0 out of 10, Very good, (13 reviews)
"Great place to get away. "
United States
Jason W.
The price is CA $122
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
{Riverbend Retreat} – Cozy Cabin

13. Charming 3-bedroom house in Mountain City beautiful big coy pond in backyard

Charming 3-bedroom house in Mountain City beautiful big coy pond in backyard
Mountain City
10.0 out of 10, Exceptional, (34 reviews)
"This home is an absolute gem! Clean, spacious, and so many special touches that feels like home. There's fans in every bedroom, the beds were very comfortable with warm comforters. And the outdoor oasis in the back yard, magical! We will stay here again!"
United States
Brandi
The price is CA $175
CA $267 total
includes taxes & fees
Nov 9 - Nov 10
Charming 3-bedroom house in Mountain City beautiful big coy pond in backyard

14. The Carolina Place, walking distance to downtown

The Carolina Place, walking distance to downtown
West Jefferson
10.0 out of 10, Exceptional, (150 reviews)
"Perfect little place for a trip to West Jefferson. Walkable to the main street. Home was very clean and well appointed."
United States
Patti L.
The price is CA $196
CA $396 total
includes taxes & fees
Nov 16 - Nov 17
The Carolina Place, walking distance to downtown

15. Rudy Cabin

Rudy Cabin
West Jefferson
9.6 out of 10, Exceptional, (4 reviews)
"Was a nice place "
United States
laura m.
The price is CA $120
CA $182 total
includes taxes & fees
Nov 30 - Dec 1
Rudy Cabin

16. Cozy Cabin Near Grayson Highlands State Park

Cozy Cabin Near Grayson Highlands State Park
Whitetop
10.0 out of 10, Exceptional, (104 reviews)
"Amazing cabin! Very clean, beautiful property and the most comfortable beds! Would stay there again:)"
United States
Ava L.
The price is CA $158
CA $287 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Cabin Near Grayson Highlands State Park

17. Cozy little cottage right in the friendly town of Damascus.

Cozy little cottage right in the friendly town of Damascus.
Damascus
8.0 out of 10, Very good, (33 reviews)
"Perfect little town to get out of the hustle and bustle"
United States
Angi
The price is CA $129
CA $258 total
includes taxes & fees
Nov 8 - Nov 9
Cozy little cottage right in the friendly town of Damascus.

18. Tiny House on Top of a Hill: SPECTACULAR VIEWS!

Tiny House on Top of a Hill: SPECTACULAR VIEWS!
Fleetwood
9.8 out of 10, Exceptional, (163 reviews)
"There is a beautiful view from the cabin."
United States
Richard
The price is CA $100
CA $198 total
includes taxes & fees
Nov 8 - Nov 9
Tiny House on Top of a Hill: SPECTACULAR VIEWS!

19. The Great Escape

The Great Escape
West Jefferson
10.0 out of 10, Exceptional, (72 reviews)
"The house was exactly as on the website. We felt nestled away in the woods. While it felt secluded, we close to the main street, a grocery store, winery, and West Jefferson State Park. We will definitely be back! Highly recommend."
United States
LeAnn S.
The price is CA $192
CA $492 total
includes taxes & fees
Nov 9 - Nov 10
The Great Escape

20. The Laurel - Peaceful 3Bdrm Mountain River Farmhouse Retreat on 4 Acres

The Laurel - Peaceful 3Bdrm Mountain River Farmhouse Retreat on 4 Acres
Creston
The price is CA $421
CA $498 total
includes taxes & fees
Nov 8 - Nov 9
The Laurel - Peaceful 3Bdrm Mountain River Farmhouse Retreat on 4 Acres
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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Top Ashland Hotel Reviews

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals close to top points of interest in Ashland, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Ashland?

Creekside Cottage in Boone • 5 mil. to dtwn • with Fire Pit! : This vacation home rental outside of Ashland is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Ashland?

While you're exploring the area, New River and Whitetop Mountain are a couple of picturesque spots to get outside and enjoy nature. Mountain Aire Golf Club and Jefferson Landing are a couple of places you'll find in the larger area.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can reserve for several days or more in Ashland. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.