A cable-stayed bridge over a river with snow-covered mountains in the background.

Holiday Homes in Portsmouth

  • 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Portsmouth holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a ceiling fan.

1. 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 €237
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom house in wonderful Portsmouth with AC, WiFi
A single-story house with a covered porch, a small garden, and a large tree in the background.

2. 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 €343
includes taxes & fees
26 Oct - 27 Oct
Visit The Sage Door House
A bedroom with a bed, a bedside table, a mirror, a window, and a hanging chair.

3. 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 €152
includes taxes & fees
5 Oct - 6 Oct
Pet-friendly cottage bordering Shawnee State Forest. Minutes from Shawnee State Park, Roosevelt Lake, Turkey Creek Lake, nature center, and hiking trails.
Exterior detail

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

Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
Portsmouth
The price is €465
includes taxes & fees
30 Sept - 1 Oct
Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More
A room with a television on a wooden cabinet, a window with floral curtains, and a power outlet on the wall.

5. 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, (1 review)
"All was good .....6ppnëhhc"
United States
anthony b.
The price is €135
includes taxes & fees
13 Oct - 14 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.
A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

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

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
9.8 out of 10, Exceptional, (20 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is €178
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house located in beautiful wooded setting!
A house with a porch and a gazebo by a pond.

7. Green Acres

Green Acres
Minford
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay, host were 10/10"
United States
Kenneth B.
The price is €261
includes taxes & fees
13 Oct - 14 Oct
Green Acres
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

8. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
8.8 out of 10, Excellent, (6 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is €157
includes taxes & fees
12 Oct - 13 Oct
Charming 3BR Home - Near KDMC & Downtown
A hot tub with a control panel and a wooden cabinet.

9. 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, (15 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 €149
includes taxes & fees
30 Sept - 1 Oct
Charming Home with private Hot Tub and Fire Pit
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

10. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (25 reviews)
"Very nice stay. "
United States
Jennifer J.
The price is €378
includes taxes & fees
30 Sept - 1 Oct
Grain Bin - Unique Stay
A covered outdoor area with a set of stairs leading up to a seating area with two chairs and a small table.

11. 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.
Fall is here, autumnal colors are beginning to show in the hills of Eastern KY!
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

12. 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 €291
includes taxes & fees
12 Oct - 13 Oct
Cozy Fonzie Flat
A small, single-story cabin with a porch, a front door, and a wreath decoration.

13. “Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking

“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
West Union
10.0 out of 10, Exceptional, (2 reviews)
"Clean, peaceful and relaxing!"
United States
April V.
The price is €185
includes taxes & fees
13 Oct - 14 Oct
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
A cozy living room with a fireplace, a dining area, and a kitchen visible through an open doorway.

14. La'Chic Boutique Bungalow 3 Beds/1.5Baths

La'Chic Boutique Bungalow 3 Beds/1.5Baths
Ashland
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed all the comfort of home."
United States
scott j.
The price is €277
includes taxes & fees
12 Oct - 13 Oct
La'Chic Boutique Bungalow 3 Beds/1.5Baths
A balcony with a view of a lake, a grassy lawn, and a building in the background.

15. White Lake Retreat | Lakefront Views | Dock

White Lake Retreat | Lakefront Views | Dock
Waverly
The price is €632
includes taxes & fees
3 Oct - 4 Oct
White Lake Retreat | Lakefront Views | Dock
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 Portsmouth Hotel Reviews

Ramada by Wyndham Catlettsburg/Ashland

Ramada by Wyndham Catlettsburg/Ashland

8/10 Good
"It was a very clean hotel and the staff was super friendly. I didn’t care for no curtains on the windows. They had shades. The breakfast was pretty good but didn’t have any protein on it. The pool area was clean."
Kimberly 2-night trip
Posted 16 hours ago
Ramada by Wyndham Catlettsburg/Ashland

Find out more about Portsmouth

Portsmouth Holiday Homes information

Number of reviews
109
Accommodation
48 Holiday Homes
Lowest Price
€135
Highest Price
€632