Greenup County Vacation Rentals from CA $184: Short-Term Rentals for 2026

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

Our top choices for Greenup County vacation rentals

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!

Raceland

Melinda K.

CA $281 total

includes taxes & fees

Nov 15 - Nov 16

A compact bedroom with a bed, a small bedside table, and a window.

2. Cozy All Season 5th wheel camper in tranquil Greenup, ky.

Greenup

CA $271 total

includes taxes & fees

Oct 18 - Oct 19

A wooden covered bridge with a stone pathway leading to a small stream.

3. Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

Garrison

Phillip

CA $228 total

includes taxes & fees

Oct 21 - Oct 22

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

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

Grayson

Ronald S.

CA $167 total

includes taxes & fees

Oct 20 - Oct 21

A living room with a sofa, armchairs, a rug, and a cabinet.

5. Grab a latte at the coffee shop downstairs, then walk a block to the floodwall where you'll find 2000 feet of murals showcasing the history of Portsmouth. After that, walk back up 2nd Street and check out the antique shops and local restaurants.

Portsmouth

Tammy

CA $207 total

includes taxes & fees

Nov 16 - Nov 17

A red brick building with a white door and a small window.

6. Grab a latte at the coffee shop, then walk a block to the floodwall where you'll find 2000 feet of murals showcasing the history of Portsmouth. After that, walk back up 2nd Street and check out the antique shops and local restaurants.

Portsmouth

Erin B.

CA $218 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor patio area with wicker furniture, a brick wall, and string lights.

7. The Kitchie Kottage/ House

Portsmouth

Taylor O.

CA $335 total

includes taxes & fees

Nov 4 - Nov 5

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

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

Portsmouth

eric

CA $387 total

includes taxes & fees

Oct 26 - Oct 27

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Greenup County Hotel Reviews

Holiday Inn Portsmouth Downtown by IHG

10/10 Excellent

"Everything was good"

DoubleTree by Hilton Huntington

10/10 Excellent

"I thought I was going to write a bad review until I got my bill. This was the most polite and helpful staff I’ve ever dealt with in a hotel, and they made everything right in the end. So, in the end I had a nice clean room, a nice shower (dirty, sweaty work had me showering twice a day), and paid a fair price for it. What I didn’t like was that everything seemed like it was going to be an up charge: I registered online and it showed me breakfast was an option —for $8 per day, but would not let me select it. I informed them and asked for this on check-in, was told I was good to go, and then was given a bill for 2 days of $18 each at each breakfast. I refused to sign but expected I was charged anyway. I was initially upset I spent $8 on breakfast… but I would not pay $18–the breakfast was not very good. Rubbery biscuits, flavorless gravy, hard pancakes, didn’t know I had to ask for coffee so no coffee first breakfast There was no mention that there is no parking lot. Parking… you guessed it, extra $10 a day for a parking garage on the next block that connects via 2nd floor skybridge, and my room was in the 11th floor. So… I had long rough days with a 1,000 yard walk at work for parking, to then have to walk a block when I got back. Good exercise at least. The garage sign that showed hotel parking was illegible at night, and coming back from work at 11pm, I drove around the block for almost an hour before getting good directions from staff, and went to 2 wrong garages first…"

SureStay by Best Western Grayson

10/10 Excellent

"The room was really clean, even the hot tub felt like it was extremely well-maintained! It was very spacious and comfy too. The breakfast was a lovely and delicious- AND HOT - buffet spread, including all the good stuff (biscuits and gravy 😋). My daughter loved it. The orange juice was ice cold and delicious. The property was nice, plenty of parking, helpful staff. The pool was *so nice* and not being chlorine filled made it so much nicer for my kiddo and I. Plenty of vending machines on site for snacks and cold drinks without leaving, and we just had to cross the back parking lot to reach one of the best Mexican restaurants ive eaten at in ages! My family and I would stay here again in a heartbeat - all the good stuff at a rate i felt was really affordable and consistent."

Find out more about Greenup County

Everything you need to know about Greenup County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenup County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenup County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenup County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenup County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenup County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenup County vacation rentals we have selected for you start as low as CA $184 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenup County rentals

At Expedia, we put the best Greenup County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenup County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenup County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenup County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Greenup County vacation rentals

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

2. Cozy All Season 5th wheel camper in tranquil Greenup, ky.

3. Secluded cabin located on 400 acres in the beautiful hills of Kentucky.

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

5. Grab a latte at the coffee shop downstairs, then walk a block to the floodwall where you'll find 2000 feet of murals showcasing the history of Portsmouth. After that, walk back up 2nd Street and check out the antique shops and local restaurants.

6. Grab a latte at the coffee shop, then walk a block to the floodwall where you'll find 2000 feet of murals showcasing the history of Portsmouth. After that, walk back up 2nd Street and check out the antique shops and local restaurants.

7. The Kitchie Kottage/ House

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

9. Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

10. Quaint, spacious, & relaxing; come stay with us, you'll enjoy the details.

11. Kate’s Cottage cozy 1-bedroom cottage nestled in the woods

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

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

14. Visit The Sage Door House

15. Charming Home with private Hot Tub and Fire Pit

16. Cozy Fonzie Flat

17. Private Hot Tub Cabin Bordering Shawnee State Forest | Fire Pt | Starlink

18. Charming 3BR Home - Near KDMC & Downtown

19. Cozy camper in charming Rush with direct trail access rush off road park

20. Newly transformed farm cottage off the beaten path!

Find vacation rentals that suit your style

Top Greenup County Hotel Reviews

Holiday Inn Portsmouth Downtown by IHG

DoubleTree by Hilton Huntington

Days Inn by Wyndham Grayson

Fairfield Inn & Suites By Marriott Ashland

Delta Hotels by Marriott Huntington Downtown

Best Western River Cities

SureStay by Best Western Grayson

Find out more about Greenup County