Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Exterior

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10.0 out of 10, Exceptional, (270)
"Lovely home fully stocked to cover all your needs. "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Cozy private getaway built for couples to reconnect !!
Interior

Cozy private getaway built for couples to reconnect !!

10.0 out of 10, Exceptional, (46)
"My only concern about the property would be that there is another rental property prerty close. The property is very new, clean and well kept. Been to many properties and this is one of the very best. We will definitely be back for this property and would love to rent the other property as well."
Cozy private getaway built for couples to reconnect !!
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
Outdoor dining

Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (332)
"Peaceful and beautiful. The cabin feels like home so comfortable And clean. If you want a quiet place away from the city this is a great place. "
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
The Angler
Microwave, oven, stovetop

The Angler

9.8 out of 10, Exceptional, (6)
The Angler
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Fridge, microwave, oven, stovetop

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

10.0 out of 10, Exceptional, (142)
"Completely set up for all your conveniences very comfortable furniture! Ease of check in and check out!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
Exterior

Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (106)
"Great place to get away. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Oven, stovetop, dishwasher

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

9.8 out of 10, Exceptional, (39)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Cowboy Saloon Cabin
Terrace/patio

Cowboy Saloon Cabin

9.4 out of 10, Exceptional, (15)
"The utensils were dirty, a lot of bugs, spider webs. I think the porch's should of been swept off and just cleaned a little better. Windows were dirty. Inside cabin was very nice and clean, except for the utensils. We will definately visit again. Thank you. Lianne"
The price is CA $186
CA $269 total
includes taxes & fees
Sep 2 - Sep 3
Cowboy Saloon Cabin
Unique stay, hot tub, secluded
Interior

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (12)
"We really enjoyed our stay! "
The price is CA $175
CA $359 total
includes taxes & fees
Sep 15 - Sep 16
Unique stay, hot tub, secluded
Glamping Cabin | Huge Window | Over a Creek
Property grounds

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (5)
"Beautiful location ."
The price is CA $109
CA $170 total
includes taxes & fees
Sep 2 - Sep 3
Glamping Cabin | Huge Window | Over a Creek
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
Dining

Amish-built cabin, serene and peaceful with pond and private dock for fishing.

10.0 out of 10, Exceptional, (21)
"The property was beautiful. The cabin was clean and well maintained. "
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
Griffis Game Hunting and/or Getaway
Exterior

Griffis Game Hunting and/or Getaway

9.8 out of 10, Exceptional, (26)
"Very nice place. We will be back again in the future thank you for everything "
The price is CA $186
CA $302 total
includes taxes & fees
Sep 4 - Sep 5
Griffis Game Hunting and/or Getaway
Secluded cabin located in Amish country
Property grounds

Secluded cabin located in Amish country

10.0 out of 10, Exceptional, (88)
"Thank you for our stay. Your place is beautiful and such a great location. Booking for October "
Secluded cabin located in Amish country
Private cabin on 80 acre farm in Adams County Ohio
1 bedroom, WiFi, bed sheets

Private cabin on 80 acre farm in Adams County Ohio

10.0 out of 10, Exceptional, (18)
"Beautiful area and very quiet and restful. The hosts were exceptional and very responsive. Loved our stay and would definitely look for a return visit. "
Private cabin on 80 acre farm in Adams County Ohio
Home away from Home! - 1BR apartment in Maysville
1 bedroom

Home away from Home! - 1BR apartment in Maysville

10.0 out of 10, Exceptional, (7)
"Property manager is the sweetest and super helpful and available. The apartment was clean and comfortable. I highly recommend the eatery downstairs for lunch ir supper!!"
The price is CA $117
CA $147 total
includes taxes & fees
Sep 2 - Sep 3
Home away from Home! - 1BR apartment in Maysville
Bear Necessities Cabin - What Else Do You Need?
Fridge, microwave, stovetop, coffee/tea maker

Bear Necessities Cabin - What Else Do You Need?

10.0 out of 10, Exceptional, (1)
"Great little spot! Cabin is super nice inside and out."
The price is CA $142
CA $248 total
includes taxes & fees
Sep 7 - Sep 8
Bear Necessities Cabin - What Else Do You Need?
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Exterior

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

10.0 out of 10, Exceptional, (35)
"I had a great time while I was there. Nice and peaceful. Ken and Cindy and the dogs are awesome hosts. I'd definitely go again. "
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Fridge, microwave, oven, stovetop

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

9.4 out of 10, Exceptional, (3)
"This was a great stay. Very easy to find and in a good area. Very clean and nice. "
The price is CA $278
CA $377 total
includes taxes & fees
Sep 2 - Sep 3
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)
Outdoor dining

Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)

10.0 out of 10, Exceptional, (4)
"Had everything we needed with easy access. Perfect environment for a weekend getaway. Having our own private dock made it even better, an overall fantastic experience"
Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)
Country Cabin in Amish Country
Fridge, microwave, oven

Country Cabin in Amish Country

9.6 out of 10, Exceptional, (8)
"The cabin was absolutely gorgeous. I would recommend it to all of my friends "
The price is CA $144
CA $259 total
includes taxes & fees
Sep 3 - Sep 4
Country Cabin in Amish Country
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

Find out more about Winchester

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 $109 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Unique stay, hot tub, secluded: Visitors like this Winchester vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

What’s there to see and do in Winchester?

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

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.