A blue bridge over a river, a park with a paved walkway, and a lamppost.

Holiday Homes in Ashland

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ashland holiday homes

A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

1. Charming 2-bedroom house located in beautiful wooded setting!

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is NZ$348
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom house located in beautiful wooded setting!
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

2. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
9.0 out of 10, Wonderful, (9 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is NZ$403
includes taxes & fees
27 Oct - 28 Oct
Charming 3BR Home - Near KDMC & Downtown
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

3. Cozy Fonzie Flat

Cozy Fonzie Flat
Ashland
10.0 out of 10, Exceptional, (1 review)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is NZ$563
includes taxes & fees
27 Oct - 28 Oct
Cozy Fonzie Flat
A living room with a ceiling fan, a sofa, a coffee table, and a window with curtains.

4. Corner Cottage 2 bedroom pets welcome and close to downtown

Corner Cottage 2 bedroom pets welcome and close to downtown
Ashland
9.0 out of 10, Wonderful, (4 reviews)
"The host communicated promptly about pet friendly place. Home was great for my stay and needs."
United States
Jennifer A.
The price is NZ$567
includes taxes & fees
7 Nov - 8 Nov
Corner Cottage 2 bedroom pets welcome and close to downtown
A covered outdoor area with a set of stairs leading up to a seating area with two chairs and a small table.

5. Fall is here, autumnal colors are beginning to show in the hills of Eastern KY!

Fall is here, autumnal colors are beginning to show in the hills of Eastern KY!
Grayson
8.8 out of 10, Excellent, (3 reviews)
"The home was as described.. clean .. location as great … bed was comfy!! Will definitely look to stay again!!"
United States
Ronald S.
The price is NZ$208
includes taxes & fees
27 Oct - 28 Oct
Fall is here, autumnal colors are beginning to show in the hills of Eastern KY!
A cozy living room with a fireplace, a high ceiling with exposed beams, and a comfortable seating area.

6. Spacious Family Home w/ Fireplace & Fire Pit

Spacious Family Home w/ Fireplace & Fire Pit
Grayson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home, had a great stay. Will stay again."
United States
Kelly F.
The price is NZ$977
includes taxes & fees
26 Oct - 27 Oct
Spacious Family Home w/ Fireplace & Fire Pit
A hot tub with a control panel and a wooden cabinet.

7. Charming Home with private Hot Tub and Fire Pit

Charming Home with private Hot Tub and Fire Pit
South Point
10.0 out of 10, Exceptional, (18 reviews)
"The cleanliness and the small special items example the bottle of wine and snacks if we wanted them. Will definitely stay here again if we travel that way. "
United States
Elizabeth C.
The price is NZ$315
includes taxes & fees
13 Nov - 14 Nov
Charming Home with private Hot Tub and Fire Pit
A modern living room with a dark wall, two wall-mounted lights, a patterned rug, a brown sofa with blue cushions, a black chair, and a window with curtains.

8. The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out

The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
Huntington
10.0 out of 10, Exceptional, (23 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is NZ$431
includes taxes & fees
2 Nov - 3 Nov
The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
A spacious living room with a wooden dining table, leather sofas, and mounted deer heads.

9. 2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Kenova
10.0 out of 10, Exceptional, (63 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is NZ$408
includes taxes & fees
1 Nov - 2 Nov
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a wooden countertop.

10. The Cedar House -Cute, inviting, Charming and memorable.

The Cedar House -Cute, inviting, Charming and memorable.
Barboursville
The price is NZ$517
includes taxes & fees
22 Nov - 23 Nov
The Cedar House -Cute, inviting, Charming and memorable.
A single-story house with a covered porch, a small garden, and a large tree in the background.

11. Visit The Sage Door House

Visit The Sage Door House
Wheelersburg
10.0 out of 10, Exceptional, (2 reviews)
"Great place with more than adequate accommodations. "
United States
kandace F.
The price is NZ$696
includes taxes & fees
15 Nov - 16 Nov
Visit The Sage Door House
An outdoor patio area with wicker furniture, a brick wall, and string lights.

12. The Kitchie Kottage/ House

The Kitchie Kottage/ House
Portsmouth
10.0 out of 10, Exceptional, (26 reviews)
"Clean Place, Great Host!"
United States
Taylor O.
The price is NZ$404
includes taxes & fees
4 Nov - 5 Nov
The Kitchie Kottage/ House
A cozy living room with a fireplace, a dog lying on the floor, and a door leading outside.

13. Spacious Historic 5-bedroom house in charming Barboursville with AC

Spacious Historic 5-bedroom house in charming Barboursville with AC
Barboursville
10.0 out of 10, Exceptional, (2 reviews)
"Very cozy and nice place!"
United States
Joseph S.
The price is NZ$1,099
includes taxes & fees
27 Oct - 28 Oct
Spacious Historic 5-bedroom house in charming Barboursville with AC
A living room with a sofa, coffee table, and a chandelier.

14. Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Huntington
The price is NZ$2,545
includes taxes & fees
25 Oct - 26 Oct
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
A modern kitchen with white cabinets, stainless steel appliances, and a ceiling fan.

15. Charming 2-bedroom house in wonderful Portsmouth with AC, WiFi

Charming 2-bedroom house in wonderful Portsmouth with AC, WiFi
Portsmouth
10.0 out of 10, Exceptional, (17 reviews)
"Place was very clean and well kept will definitely stay here again"
United States
eric
The price is NZ$469
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom house in wonderful Portsmouth with AC, WiFi
A house with a porch and a gazebo by a pond.

16. Green Acres

Green Acres
Minford
10.0 out of 10, Exceptional, (29 reviews)
"The property was immaculate, gorgeous, and my kids had a lot of fun kayaking and fishing in the pond. We saw blue herons, deer and fish during our brief stay."
United States
Jessica J.
The price is NZ$561
includes taxes & fees
25 Oct - 26 Oct
Green Acres
A two-story house with a front porch, steps leading to the entrance, and a small garden area.

17. Charming 3-bedroom house in terrific Portsmouth hilltop neighbourhood.

Charming 3-bedroom house in terrific Portsmouth hilltop neighbourhood.
Portsmouth
8.6 out of 10, Excellent, (18 reviews)
"Nice place well informed easy check in...lots of room...well done..thanks"
United States
earl l.
The price is NZ$567
includes taxes & fees
6 Nov - 7 Nov
Charming 3-bedroom house in terrific Portsmouth hilltop neighbourhood.
Exterior detail

18. Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More

Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
Portsmouth
The price is NZ$916
includes taxes & fees
26 Oct - 27 Oct
Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
A bedroom with a bed, a bedside table, a mirror, a window, and a hanging chair.

19. Pet-friendly cottage bordering Shawnee State Forest. Minutes from Shawnee State Park, Roosevelt Lake, Turkey Creek Lake, nature center, and hiking trails.

Pet-friendly cottage bordering Shawnee State Forest. Minutes from Shawnee State Park, Roosevelt Lake, Turkey Creek Lake, nature center, and hiking trails.
West Portsmouth
9.4 out of 10, Exceptional, (10 reviews)
"Great stay. This home is huge and spacious and was very clean and well kept. Communication with the owner was quick and easy. Would highly recommend! "
United States
Amanda L.
The price is NZ$296
includes taxes & fees
23 Nov - 24 Nov
Pet-friendly cottage bordering Shawnee State Forest. Minutes from Shawnee State Park, Roosevelt Lake, Turkey Creek Lake, nature center, and hiking trails.
A modern living room with a sofa, a lamp, and a round table.

20. Escape the hustle and reconnect with nature at Outpost, your stay tucked along the borders of Shawnee State Forest. Whether you're seeking a solo retreat, a romantic getaway, or a weekend with friends, this spot offers a blend of woods & comfort.

Escape the hustle and reconnect with nature at Outpost, your stay tucked along the borders of Shawnee State Forest. Whether you're seeking a solo retreat, a romantic getaway, or a weekend with friends, this spot offers a blend of woods & comfort.
West Portstmouth
8.0 out of 10, Very good, (2 reviews)
"All was good .....6ppnëhhc"
United States
anthony b.
The price is NZ$284
includes taxes & fees
23 Nov - 24 Nov
Escape the hustle and reconnect with nature at Outpost, your stay tucked along the borders of Shawnee State Forest. Whether you're seeking a solo retreat, a romantic getaway, or a weekend with friends, this spot offers a blend of woods & comfort.
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

Holiday Inn Portsmouth Downtown by IHG

Holiday Inn Portsmouth Downtown by IHG

10/10 Excellent
"This was our first time staying at Holiday Inn Portsmouth Downtown by IHG, as we were traveling through the area to attend a wedding. From the moment we pulled up, everything was smooth and hassle-free. Parking was super easy, and check-in was a breeze thanks to the front desk staff, who were all extremely polite, welcoming, and helpful. Our room was very clean and looked to be freshly renovated. The shower pressure was great, the hot water was hot, and there was plenty of space for two people to unpack and feel completely comfortable. As a huge bonus for coffee drinkers, they had cream and sugar readily available right at the front desk, which is a huge deal since there is never enough in the room. The location itself is fantastic as well, right downtown with plenty of local spots and attractions within easy walking distance. It made our trip completely stress-free. If we happen to be traveling through or visiting the area again in the future, we will definitely stay here."
Jason 2-night trip
Posted 19 hours ago
Holiday Inn Portsmouth Downtown by IHG

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
224
Accommodation
64 Holiday Homes
Lowest Price
NZ$208
Highest Price
NZ$2,545