Winchester Vacation Rentals

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Check prices for these dates

Tonight
Aug 9 - Aug 10
Tomorrow
Aug 10 - Aug 11
Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24

Vacation Rentals in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Enjoy a meal under the stars at this serene outdoor dining area, complete with a picnic table and twinkling string lights.

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

9.8 out of 10, Exceptional, (191)
"We had a great stay! Ted was very communicative and thoughtful of our needs. The house fit our group perfectly and was so much fun. We enjoyed the games onsite and the indoor pool. We were able to visit and relax. A perfect weekend getaway! "
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Enjoy a game of basketball in our indoor court with two hoops and a high ceiling featuring a geometric pattern.

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (194)
"This was so relaxing! Way better than the old bar hopping. Very nice and clean."
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Cardinal Cottage - 2 bedroom cozy home
Welcome to this charming single-story home with a cozy front porch and inviting garden.

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (20)
"Great stay "
The price is ￥14,694
￥26,332 total
includes taxes & fees
Aug 25 - Aug 26
Cardinal Cottage - 2 bedroom cozy home
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Relax in this spacious living area with a large window offering a view of the outdoors, a comfortable sofa, and a kitchen with a bar area.

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.0 out of 10, Wonderful, (10)
"Nice, quiet, peaceful."
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Retro Home Close to Campus
Enjoy meals in style with a table set for four, featuring a geometric pattern and comfortable black chairs.

Retro Home Close to Campus

9.8 out of 10, Exceptional, (6)
The price is ￥19,837
￥43,612 total
includes taxes & fees
Aug 18 - Aug 19
Retro Home Close to Campus
Recently remodeled Colonial-style home with room for the whole family!
Traditional home with a charming front porch and well-manicured yard.

Recently remodeled Colonial-style home with room for the whole family!

10.0 out of 10, Exceptional, (37)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!
Charming 3-bedroom house with AC, WiFi in Greenville
Stroll through the beautifully manicured lawn to a charming shed surrounded by lush trees.

Charming 3-bedroom house with AC, WiFi in Greenville

10.0 out of 10, Exceptional, (2)
"Nice place good location. Would highly recommend to anyone."
The price is ￥23,070
￥36,442 total
includes taxes & fees
Aug 14 - Aug 15
Charming 3-bedroom house with AC, WiFi in Greenville
3 br country home close to town with hot tub
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave.

3 br country home close to town with hot tub

9.4 out of 10, Exceptional, (29)
"Very nice home and I appreciated the small fence yard for my dog."
3 br country home close to town with hot tub
Pet-Friendly Greenville Home w/ Private Yard
Modern kitchen with white cabinetry, stainless steel appliances, and a window.

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (21)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard
THE STARR LOFT- Earlham, IUEast, Historic District
Relax in a charming room with a comfortable seating area, sofa, and round table, featuring a large chandelier and large windows.

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (30)
"I wasn't expecting that a visit to my small hometown would end up being the nicest vacation stay I've had but it was. Walking distance to some fun restaurants and a great record store. Property itself was beautiful and well maintained in a renovated loft space. Lots of charm and attention to detail. This place makes me want to find reasons to visit Richmond more often!"
THE STARR LOFT- Earlham, IUEast, Historic District
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Enjoy cooking in the fully equipped kitchen with stainless steel appliances and white cabinetry.

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The price is ￥14,547
￥26,990 total
includes taxes & fees
Aug 10 - Aug 11
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Cozy RV close to the Reservoir
Cozy seating area with leather couch and small table, perfect for relaxing.

Cozy RV close to the Reservoir

2.0 star property
6.0 out of 10, (1)
"This was a really neat idea, and the kids were very excited to stay in an RV. I will start by saying it was very clean. It was not advertised that this was on private property right next to the house until check in time. The location was also not optimal because it was right next to the main road where you could hear every car, and the entrance was across from what looked like a lot of junk. . we had to deal with a dog barking all night, long, but we made the best of all this. The only thing...
The price is ￥15,208
￥23,617 total
includes taxes & fees
Aug 10 - Aug 11
Cozy RV close to the Reservoir
The Red House
Guests can relax in a serene outdoor setting surrounded by lush greenery, enjoying the warmth of a central fire pit.

The Red House

9.6 out of 10, Exceptional, (18)
"This was our 2nd stay at the red house while in town to visit family. Perfect location and space for our family of four. Friendly communication with the owner. Would happily stay again. Recommend!"
The Red House
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Traditional home with a central entrance, flanked by windows, set amidst a well-manicured lawn and lush greenery.

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.8 out of 10, Exceptional, (24)
"Very unique quaint cottage hidden from the city. Loved the forested area around it with the patio to the side. We saw"
The price is ￥16,898
￥32,092 total
includes taxes & fees
Aug 25 - Aug 26
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Relax in the lounge area with a leather sofa, wooden bench, and dining table.

Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10

10.0 out of 10, Exceptional, (1)
"We had an AMAZING time at Elm & Ivy!! What a beautiful venue for a chill bachelorette party!! There were so many perfect little touches that added to our stay. Highly recommend- we already talked about coming back again!!"
The price is ￥51,429
￥58,776 total
includes taxes & fees
Aug 12 - Aug 13
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Cozy living space with a kitchen and living area, featuring a sofa, armchair, and oven.

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

9.8 out of 10, Exceptional, (8)
"Very clean and great amenities. Will be booking there again in the future."
The price is ￥10,447
￥24,045 total
includes taxes & fees
Aug 13 - Aug 14
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Enjoy a bright and airy living space with a kitchen and living area, featuring a sofa, coffee table, and rug.

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.8 out of 10, Exceptional, (16)
"Always a pleasure and the location is perfect for seeing family!"
The price is ￥8,596
￥20,326 total
includes taxes & fees
Aug 11 - Aug 12
New Hagerstown Apartment - Self Check-in. Sleeps 4+
5 min walk to BSU Campus - Quiet Neighborhood
Enjoy meals in this dining area with a round table and six chairs.

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (67)
"We're in town for a sporting event and stayed in this property. Excellent on all accounts and would definitely stay here again. "
5 min walk to BSU Campus - Quiet Neighborhood
Cozy Cabin with fireplace, hot tub & hiking trails
Relax by the serene pool surrounded by lush greenery and a charming gazebo.

Cozy Cabin with fireplace, hot tub & hiking trails

7.4 out of 10, Good, (3)
"It’s secluded and peaceful. We had a very nice time. The pool and the hot tub were perfect. The cabin was fun!"
Cozy Cabin with fireplace, hot tub & hiking trails
Newly renovated studio in Hagerstown--Self Check-in
Enjoy a compact apartment with a kitchenette, dining area, and cozy seating space.

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Loved the property close to whatever you need for seeing local attractions or family/friends."
The price is ￥6,781
￥18,351 total
includes taxes & fees
Aug 18 - Aug 19
Newly renovated studio in Hagerstown--Self Check-in
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

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

10/10 Excellent
"Lady that checked us in was awesome "
Lynwood 1-night trip
Posted 21 hours ago
Baymont by Wyndham Richmond I-70

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, we give you a choice of vacation rentals close to popular points of interest in Winchester, or you can choose a more secluded option if you're looking for relaxation. Winchester is known for its golf courses.

What's the top vacation rental that Winchester has to offer?

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!: Visitors like this Winchester vacation home rental. It is located in a rural location and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Winchester?

Expedia has 3 vacation rentals for your stay in Winchester.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and Burlington Lake are a couple of picturesque spots to get outside and enjoy nature. Winchester Golf Club and Winchester Speedway are other places to visit while you're in town.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Winchester. Vacation rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.