Winchester Vacation Rentals from ￥17,984: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Winchester has to offer?

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR! : Visitors like this Winchester vacation home rental. It is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

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Our top choices for Winchester vacation rentals

2 bedrooms, iron/ironing board, WiFi, bed sheets

1. The Cabin at 114 Main Street with Hot Tub

Augusta

￥43,774 total

includes taxes & fees

Aug 11 - Aug 12

2. Bertha's Cabin: Rustic Ohio River Retreat

Augusta

￥44,760 total

includes taxes & fees

Aug 10 - Aug 11

3. Del's Cabin: River Retreat Sleeps 8 w/ Hot Tub

Augusta

￥113,631 total

includes taxes & fees

Aug 10 - Aug 11

4. Country Cabin in Amish Country

Peebles

Rodney C.

￥29,549 total

includes taxes & fees

Aug 10 - Aug 11

5. The Bear Den (Secluded in Amish Country and peaceful)

Peebles

BeechRidgeOutfitters

￥28,555 total

includes taxes & fees

Aug 10 - Aug 11

Coffee/tea maker, fridge, microwave, oven

6. Griffis Game Hunting and/or Getaway

West Union

BRAD T.

￥34,517 total

includes taxes & fees

Aug 10 - Aug 11

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

West Union

￥30,730 total

includes taxes & fees

Aug 14 - Aug 15

8. Meadowview Guest House

Hillsboro

Tiffany

￥28,081 total

includes taxes & fees

Aug 10 - Aug 11

9. Hunter Lodge (Secluded in Amish Country and peaceful)

Peebles

Angela M.

￥30,290 total

includes taxes & fees

Aug 10 - Aug 11

10. Deer Lodge (Secluded in Amish Country and peaceful)

Peebles

William B.

￥29,186 total

includes taxes & fees

Aug 10 - Aug 11

11. Secluded in Amish Country and peaceful

Peebles

Gregory H.

￥28,555 total

includes taxes & fees

Aug 10 - Aug 11

12. Glamping Cabin | Huge Window | Valley and Cliff Views

Green Township

Brett W.

￥17,984 total

includes taxes & fees

Aug 10 - Aug 11

13. Glamping Cabin | Huge Window | Over a Creek

Green Township

Kristen W.

￥17,984 total

includes taxes & fees

Aug 10 - Aug 11

14. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout

Kenneth

￥28,414 total

includes taxes & fees

Aug 10 - Aug 11

15. Glamping Cabin | Huge Window | Tree House Feel

Green Township

"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."

Stuart

￥17,984 total

includes taxes & fees

Aug 10 - Aug 11

16. Cowboy Saloon Cabin

Hamersville

Jared

￥32,830 total

includes taxes & fees

Aug 10 - Aug 11

17. Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

Hamersville

Atonenent R.

￥31,000 total

includes taxes & fees

Aug 10 - Aug 11

18. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Rome

￥28,463 total

includes taxes & fees

Aug 10 - Aug 11

19. Sleeps 4| Private Bathroom | Stunning Views

Green Township

Al G.

￥24,453 total

includes taxes & fees

Aug 10 - Aug 11

20. The White Stag

Hillsboro

Gavin D.

￥25,998 total

includes taxes & fees

Aug 10 - Aug 11

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Top Winchester Hotel Reviews

French Quarter Inn

10/10 Excellent

"My room overlooked the mighty Ohio River. I am from Maysville and I used to go to sleep to the sound of the trains going through. Last night one of the longest trains I've ever seen came through and because the tracks are right beside the hotel the whole building rumbled. Loved it. Really nice room, clean as can be, updated with white comforter and good mattress. When I opened the blinds at dawn, there was a huge riverboat pulled up under my window, called the American Melody. It's not a brand new hotel but nicely refurbished. Hotel staff was patient and pleasant. Breakfast was a bit limited, but good. The Keurig coffee pod choice could have been a bit better - Great Value and Dunkin Donuts brands. The hotel is walking distance for several things, including the murals on the flood wall. Don't miss lunch at the Parc Cafe down the street. Their park around the building has life-sized bronze statues of buffalo. All in all, a really nice experience."

Beverly hills inn

10/10 Excellent

"The motel overall was great. It’s an older place so if you are going to nit pick everything that’s older. It’s not for you. The place is very laid back and the staff is great. Housekeeping came and gave us fresh towels/made the beds. It has a pool, restaurant and bar that make it very convenient. We will definitely be back."

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to top attractions in Winchester, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winchester has to offer?

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: Visitors like this Winchester vacation home rental. It is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.

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Check prices for these dates

Our top choices for Winchester vacation rentals

1. The Cabin at 114 Main Street with Hot Tub

2. Bertha's Cabin: Rustic Ohio River Retreat

3. Del's Cabin: River Retreat Sleeps 8 w/ Hot Tub

4. Country Cabin in Amish Country

5. The Bear Den (Secluded in Amish Country and peaceful)

6. Griffis Game Hunting and/or Getaway

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

8. Meadowview Guest House

9. Hunter Lodge (Secluded in Amish Country and peaceful)

10. Deer Lodge (Secluded in Amish Country and peaceful)

11. Secluded in Amish Country and peaceful

12. Glamping Cabin | Huge Window | Valley and Cliff Views

13. Glamping Cabin | Huge Window | Over a Creek

14. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

15. Glamping Cabin | Huge Window | Tree House Feel

16. Cowboy Saloon Cabin

17. Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

18. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

19. Sleeps 4| Private Bathroom | Stunning Views

20. The White Stag

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

French Quarter Inn

Quality Inn Seaman

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!

Nature's Nook Cabin

Beverly hills inn

Hillsboro Inn & Suites

Peaceful cabin with spectacular river and scenic views.

Super 8 by Wyndham Maysville KY

Brown's Motel Aberdeen

Find out more about Winchester

Frequently asked questions

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