Winchester Vacation Rentals

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Check prices for these dates

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

Our top choices for Winchester vacation 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 CA $657
CA $985 total
includes taxes & fees
Nov 13 - Nov 14
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 CA $184
CA $292 total
includes taxes & fees
Nov 13 - Nov 14
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 CA $212
CA $301 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $192
CA $286 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $201
CA $318 total
includes taxes & fees
Dec 9 - Dec 10
“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 CA $141
CA $236 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $97
CA $150 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $212
CA $301 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $172
CA $255 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $212
CA $315 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $97
CA $150 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $169
CA $230 total
includes taxes & fees
Nov 16 - Nov 17
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, (49 reviews)
"Great cabin. Very clean, fully stocked kitchen, owner is very helpful."
United States
Christy A.
The price is CA $212
CA $315 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $384
CA $557 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $97
CA $150 total
includes taxes & fees
Dec 8 - Dec 9
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 CA $159
CA $242 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $254
CA $373 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $141
CA $157 total
includes taxes & fees
Dec 12 - Dec 13
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 CA $362
CA $430 total
includes taxes & fees
Dec 2 - Dec 3
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 CA $197
CA $323 total
includes taxes & fees
Nov 17 - Nov 18
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

An outdoor seating area with tables and chairs, overlooking a river and a bridge.
French Quarter Inn

French Quarter Inn

French Quarter Inn
Maysville

8/10 Good

Great spot on the water downtown, walking distance to everything. Needs some love but overall decent cleanliness and upkeep.
Canada
Adam
Reviewed March 24, 2021
French Quarter Inn

Find out more about Winchester

Everything you need to know about Winchester 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 Winchester 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. 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 Winchester 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 Winchester vacation rentals we have selected for you start as low as CA $97 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester 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 Winchester 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 Winchester 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 Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.