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

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winchester holiday rentals

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
The price is HK$3,651
HK$5,467 total
includes taxes & fees
10 Nov - 11 Nov
Quiet Farm Escape | Fishing, Nature & Views
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.

2. 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.
The price is HK$1,019
HK$1,629 total
includes taxes & fees
13 Nov - 14 Nov
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.

3. 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.
The price is HK$1,176
HK$1,670 total
includes taxes & fees
15 Nov - 16 Nov
Deer Lodge (Secluded in Amish Country and peaceful)
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

4. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (39 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.
The price is HK$1,058
HK$1,582 total
includes taxes & fees
16 Nov - 17 Nov
Griffis Game Hunting and/or Getaway
A small, single-story cabin with a porch, a front door, and a wreath decoration.

5. “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, (3 reviews)
"Clean, peaceful and relaxing!"
United States
April V.
The price is HK$1,066
HK$1,708 total
includes taxes & fees
10 Nov - 11 Nov
“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
A hot tub in a backyard with a wooden fence and a grassy field in the background.

6. 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.
The price is HK$784
HK$1,262 total
includes taxes & fees
15 Nov - 16 Nov
Meadowview Guest House
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

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

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (4 reviews)
"Very family friendly lovely views great host and respectfully so clean very nice stay"
United Kingdom
Brett W.
The price is HK$541
HK$831 total
includes taxes & fees
10 Nov - 11 Nov
Glamping Cabin | Huge Window | Valley and Cliff Views
A kitchen with wooden cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

8. 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.
The price is HK$1,176
HK$1,670 total
includes taxes & fees
15 Nov - 16 Nov
Secluded in Amish Country and peaceful
Living area

9. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (28 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.
The price is HK$953
HK$1,433 total
includes taxes & fees
12 Nov - 13 Nov
Cowboy Saloon Cabin
A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

10. 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.
The price is HK$1,176
HK$1,733 total
includes taxes & fees
17 Nov - 18 Nov
Hunter Lodge (Secluded in Amish Country and peaceful)
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

11. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (11 reviews)
"A great way to be in nature and enjoy peace and quiet."
United States
Kendra D.
The price is HK$541
HK$831 total
includes taxes & fees
12 Nov - 13 Nov
Glamping Cabin | Huge Window | Over a Creek
A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

12. 1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and neat! Very comfortable place to stay. We enjoyed out visit and would definitely book this property again."
United States
Brenda
The price is HK$941
HK$1,333 total
includes taxes & fees
10 Nov - 11 Nov
1 Bed/1 Bath Guest House
A wooden interior with a round dining table, chairs, a welcome sign, and a window with a view.

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

The Bear Den (Secluded in Amish Country and peaceful)
Peebles
9.8 out of 10, Exceptional, (48 reviews)
"Great cabin. Very clean, fully stocked kitchen, owner is very helpful."
United States
Christy A.
The price is HK$1,176
HK$1,733 total
includes taxes & fees
17 Nov - 18 Nov
The Bear Den (Secluded in Amish Country and peaceful)
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

14. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (26 reviews)
"Very nice stay. "
United States
Jennifer J.
The price is HK$2,130
HK$3,158 total
includes taxes & fees
10 Nov - 11 Nov
Grain Bin - Unique Stay
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

15. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.6 out of 10, Excellent, (23 reviews)
"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"
Mexico
Víctor Manuel
The price is HK$541
HK$831 total
includes taxes & fees
15 Nov - 16 Nov
Glamping Cabin | Huge Window | Tree House Feel
Terrace/patio

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

Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Hamersville
9.6 out of 10, Exceptional, (26 reviews)
"This was a great stay. The property owners were fabulous. Definitely coming back ."
United States
Atonenent R.
The price is HK$882
HK$1,350 total
includes taxes & fees
10 Nov - 11 Nov
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
An outdoor patio area with a stone fire pit, a hot tub, and outdoor seating.

17. Sunset Cabin-Adults Only Hot Tub Getaway

Sunset Cabin-Adults Only Hot Tub Getaway
Hillsboro
9.8 out of 10, Exceptional, (7 reviews)
"Great weekend thank you"
United States
Kris S.
The price is HK$1,411
HK$2,172 total
includes taxes & fees
10 Nov - 11 Nov
Sunset Cabin-Adults Only Hot Tub Getaway
A cozy living room with a brown sofa, patterned armchairs, a coffee table, and a television.

18. The Angler

The Angler
Hillsboro
8.6 out of 10, Excellent, (16 reviews)
"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "
United States
Jerry P.
The price is HK$784
HK$935 total
includes taxes & fees
3 Dec - 4 Dec
The Angler
A wooden cabin interior with a four-poster bed, a fireplace, a dining table, and a sofa.

19. Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!

Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
West Union
The price is HK$1,999
HK$2,377 total
includes taxes & fees
2 Dec - 3 Dec
Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
A wooden deck with outdoor furniture, a barbecue grill, and a view of a lake.

20. Tom & Jerri's Rustic Cabin located on the lake

Tom & Jerri's Rustic Cabin located on the lake
Hamersville
9.8 out of 10, Exceptional, (16 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
The price is HK$1,094
HK$1,794 total
includes taxes & fees
10 Nov - 11 Nov
Tom & Jerri's Rustic Cabin located on the lake
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

Countryside Inn & Suites

Countryside Inn & Suites

8/10 Good
"Clean room, good continental breakfast. Staff was exceptional when a senior person in another room had an event. Cleaning staff was very good. It’s an older place, but they run it very well. 4/5."
Edward 3-night trip
Posted 1 day ago
Countryside Inn & Suites

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: This holiday home rental outside of Winchester is located on a lake, and has a patio, a selection of games and a BBQ 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 that 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 wider area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.