A historic downtown area with a prominent clock tower and a green-roofed building.

Search and Rent Winchester Condos

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
$679 nightly
The price is $697
Nov 9 - Nov 10
Total with taxes and fees
Quiet Farm Escape | Fishing, Nature & Views
A hotel lobby with a reception desk, a sofa, a chair, a desk with a telephone, and a computer.

2. Quality Inn Seaman

Quality Inn Seaman
2.5 star property
Seaman
7.2 out of 10, Good, (327 reviews)
"Close to everything that we needed clean quiet"
United States
Karen
$96 nightly
The price is $105
Dec 6 - Dec 7
Total with taxes and fees
Quality Inn Seaman
A hotel room with two beds, a desk, a TV, and a painting on the wall.

3. Country Nights Inn

Country Nights Inn
2.5 star property
West Union
7.6 out of 10, Good, (71 reviews)
"First…there was a"
United States
David
$88 nightly
The price is $97
Dec 5 - Dec 6
Total with taxes and fees
Country Nights Inn
A hotel room with a bed, bedside table, lamp, TV, and a desk with a chair.

4. Countryside Inn & Suites

Countryside Inn & Suites
2.5 star property
Mount Orab
7.4 out of 10, Good, (612 reviews)
"Loved the Free breakfast.great location."
United States
Robert
$76 nightly
The price is $86
Dec 6 - Dec 7
Total with taxes and fees
Countryside Inn & Suites
A kitchen with wooden cabinets, a white refrigerator, a stove, and a microwave. There is a dining table with chairs and a small wooden stool.

5. Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (20 reviews)
"Peaceful and Perfect. "
United States
Rodney C.
$192 nightly
The price is $200
Nov 13 - Nov 14
Total with taxes and fees
Country Cabin in Amish Country
A cozy room with wooden walls, a ceiling fan, a window with a view of greenery, a lamp, and a chair with a deer pillow.

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

Deer Lodge (Secluded in Amish Country and peaceful)
Peebles
9.8 out of 10, Exceptional, (14 reviews)
"Nice place"
United States
William B.
$222 nightly
The price is $222
Nov 15 - Nov 16
Total with taxes and fees
Deer Lodge (Secluded in Amish Country and peaceful)
A brick building with a sign reading "French Quarter Inn" and a large dome structure in front.

7. French Quarter Inn

French Quarter Inn
3.0 star property
Maysville
8.8 out of 10, Excellent, (831 reviews)
"It was an amazing stay , especially the huge bathtub ."
United States
Jessie
$109 nightly
The price is $121
Nov 8 - Nov 9
Total with taxes and fees
French Quarter Inn
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and two framed pictures on the wall.

8. Greystone Motel

Greystone Motel
2.5 star property
Hillsboro
6.8 out of 10, (192 reviews)
"Room was nice,quiet,and tidy. The workers were helpful and amazing. I just needed a night away to clear my head and that's exactly what I got."
United States
Gina
$63 nightly
The price is $70
Nov 6 - Nov 7
Total with taxes and fees
Greystone Motel
A small, single-story cabin with a porch, a front door, and a wreath decoration.

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

“Serenity Now” cozy 2BR country cabin 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.
$198 nightly
The price is $210
Nov 9 - Nov 10
Total with taxes and fees
“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
A modern living room with a dark gray sofa, a wooden coffee table, and potted plants.

10. Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro
2.5 star property
Hillsboro
7.2 out of 10, Good, (325 reviews)
"Staff was great and helpful, but room had a lot of stains on the floor, cauch and even the mattress."
United States
Dzana
$106 nightly
The price is $117
Nov 8 - Nov 9
Total with taxes and fees
Days Inn by Wyndham Hillsboro
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

11. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (38 reviews)
"Such a cute place!! We didn’t stay at the house enough to enjoy all of the amenities, but the cabin was very clean and cozy. The beds are really comfortable. The host was great too!"
United States
Daisha M.
$192 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees
Griffis Game Hunting and/or Getaway
A hotel room with two beds, a nightstand, a painting, and a bathroom visible through an open door.

12. Brown's Motel Aberdeen

Brown's Motel Aberdeen
2.0 star property
Aberdeen
7.4 out of 10, Good, (316 reviews)
"Can’t beat it for the price. Would definitely stay again but would rather stay in the office side of the hotel."
United States
Kelly
$55 nightly
The price is $61
Nov 6 - Nov 7
Total with taxes and fees
Brown's Motel Aberdeen
A hotel room with two beds, a TV, a desk, and a mirror.

13. Paragon Inn Hillsboro

Paragon Inn Hillsboro
2.0 star property
Hillsboro
7.8 out of 10, Good, (246 reviews)
"Clean, good value"
United States
charles
$76 nightly
The price is $84
Dec 6 - Dec 7
Total with taxes and fees
Paragon Inn Hillsboro
A hotel room with two beds, a cityscape painting, and a mounted air conditioner.

14. Hillsboro Inn & Suites

Hillsboro Inn & Suites
2.0 star property
Hillsboro
7.4 out of 10, Good, (65 reviews)
"Great place to stay!"
United States
Audrey
$80 nightly
The price is $88
Nov 6 - Nov 7
Total with taxes and fees
Hillsboro Inn & Suites
A bedroom with a bed, a dresser, a vanity with a mirror, and a door leading to another room.

15. Moon River Bed and Breakfast

Moon River Bed and Breakfast
3.0 star property
Maysville
10.0 out of 10, Exceptional, (11 reviews)
"Quaint town. Lovely B&B. Very friendly staff."
United States
Angela
$129 nightly
The price is $144
Nov 12 - Nov 13
Total with taxes and fees
Moon River Bed and Breakfast
A hot tub in a backyard with a wooden fence and a grassy field in the background.

16. Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (30 reviews)
"Great stay. Host was quick to respond to all questions. Every detail was thought through. Highly recommend staying here!"
United States
Kayla E.
$169 nightly
The price is $169
Nov 8 - Nov 9
Total with taxes and fees
Meadowview Guest House
A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

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

Hunter Lodge (Secluded in Amish Country and peaceful)
Peebles
10.0 out of 10, Exceptional, (50 reviews)
"We had a great stay here and would definitely come back!"
United States
kathy b.
$221 nightly
The price is $221
Nov 8 - Nov 9
Total with taxes and fees
Hunter Lodge (Secluded in Amish Country and peaceful)
Living area

18. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (27 reviews)
"Place was great we had a great time relaxing and we loved the fire pit and how they provided the wood"
United States
Anthony R.
$176 nightly
The price is $183
Nov 6 - Nov 7
Total with taxes and fees
Cowboy Saloon Cabin
A rustic cabin interior with a kitchen area, dining table, and seating.

19. Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (32 reviews)
"Nice quite place to stay."
United States
Gregory H.
$222 nightly
The price is $222
Nov 15 - Nov 16
Total with taxes and fees
Secluded in Amish Country and peaceful
A waiting area with a brown sofa, red chairs, a small table with a plant, and a bookshelf with magazines.

20. Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky
2.5 star property
Maysville
7.2 out of 10, Good, (464 reviews)
"Great stay- very clean and staff very friendly."
United States
Susan
$79 nightly
The price is $88
Nov 22 - Nov 23
Total with taxes and fees
Days Inn by Wyndham Maysville Kentucky
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 Winchester Hotel Reviews

Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

10/10 Excellent
"We loved our stay here. We enjoy quiet and privacy. This property provided that. The owners are on site, but the camper is in a secluded area. The hot tub was wonderful. When we had a problem with the toilet, Ken was quick to take care of the problem. Ken and Cindy were great to work with from making the reservations answering our questions and checking out. The whole time we were there was great. The dogs were a great addition. They are all good pups and full of love! Thank you Ken and Cindy. I am sure we will be back!"
Vicky C. 5-night trip
Posted 5 days ago
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
1,587
Accommodation
0 Condo Rentals
Lowest Price
$61
Highest Price
$697

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