A historic building with a tower, surrounded by trees and a clear sky.

Holiday Homes in Grayson

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Grayson holiday homes

A covered outdoor area with a set of stairs leading up to a seating area with two chairs and a small table.

1. 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
10.0 out of 10, Exceptional, (2 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 €110
includes taxes & fees
18 Oct - 19 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.

2. 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 €498
includes taxes & fees
19 Oct - 20 Oct
Spacious Family Home w/ Fireplace & Fire Pit
A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

3. 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, (22 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is €184
includes taxes & fees
16 Oct - 17 Oct
Charming 2-bedroom house located in beautiful wooded setting!
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

4. 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 €287
includes taxes & fees
16 Oct - 17 Oct
Cozy Fonzie Flat
A hot tub with a control panel and a wooden cabinet.

5. 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, (17 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 €167
includes taxes & fees
23 Oct - 24 Oct
Charming Home with private Hot Tub and Fire Pit
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

6. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
9.0 out of 10, Wonderful, (7 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is €171
includes taxes & fees
19 Oct - 20 Oct
Charming 3BR Home - Near KDMC & Downtown
A living room with a ceiling fan, a sofa, a coffee table, and a window with curtains.

7. 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 €302
includes taxes & fees
7 Nov - 8 Nov
Corner Cottage 2 bedroom pets welcome and close to downtown
A kitchen with a granite countertop, a black faucet, and a window with a view of a forest.

8. 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 €210
includes taxes & fees
18 Oct - 19 Oct
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
A modern kitchen with white cabinets, stainless steel appliances, and a ceiling fan.

9. 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 €249
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom house in wonderful Portsmouth with AC, WiFi
Exterior detail

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

Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
Portsmouth
The price is €464
includes taxes & fees
19 Oct - 20 Oct
Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
A two-story house with a front porch, steps leading to the entrance, and a small garden area.

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

Charming 3-bedroom house in terrific Portsmouth hilltop neighbourhood.
Portsmouth
8.4 out of 10, Very good, (17 reviews)
"Nice place well informed easy check in...lots of room...well done..thanks"
United States
earl l.
The price is €289
includes taxes & fees
6 Nov - 7 Nov
Charming 3-bedroom house in terrific Portsmouth hilltop neighbourhood.
A bedroom with a bed, a bedside table, a mirror, a window, and a hanging chair.

12. 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 €185
includes taxes & fees
29 Oct - 30 Oct
Pet-friendly cottage bordering Shawnee State Forest. Minutes from Shawnee State Park, Roosevelt Lake, Turkey Creek Lake, nature center, and hiking trails.
A room with a television on a wooden cabinet, a window with floral curtains, and a power outlet on the wall.

13. 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 €149
includes taxes & fees
27 Oct - 28 Oct
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 Grayson Hotel Reviews

Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

10/10 Excellent
"Front desk and food servi es very friendly."
Mary 1-night trip
Posted 4 hours ago
Fairfield Inn & Suites By Marriott Ashland

Find out more about Grayson

Grayson Holiday Homes information

Number of reviews
157
Accommodation
30 Holiday Homes
Lowest Price
€149
Highest Price
€534