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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester vacation rentals

1. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
$283 nightly
The price is $317
Sep 27 - Sep 28
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard

2. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
$292 nightly
The price is $326
Sep 27 - Sep 28
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A living room with hardwood flooring, a leather sofa, a mounted TV, and a door leading to a kitchen.

3. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (46 reviews)
"Really enjoyed my stay "
United States
Deb H.
$150 nightly
The price is $168
Sep 27 - Sep 28
Total with taxes and fees
Cardinal Cottage - 2 bedroom cozy home
A kitchen with wooden cabinets, a stainless steel stove, and a refrigerator.

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
$129 nightly
The price is $144
Oct 5 - Oct 6
Total with taxes and fees
New Hagerstown Apartment - Self Check-in. Sleeps 4+
A modern kitchen with stainless steel appliances, wooden cabinets, and a white tiled backsplash.

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

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Hagerstown
10.0 out of 10, Exceptional, (18 reviews)
"This is a darling place in a wonderful town. It met all of our needs and we'll definitely stay here again."
United States
Tamera
$146 nightly
The price is $164
Sep 29 - Sep 30
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
A modern living room with a sofa, armchair, and a white spiral staircase.

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.4 out of 10, Exceptional, (36 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
$195 nightly
The price is $218
Sep 27 - Sep 28
Total with taxes and fees
Quaker Hill Cottage on gated estate with fire pit & hiking trails
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

7. 'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (27 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
$292 nightly
The price is $327
Sep 28 - Sep 29
Total with taxes and fees
'Downtown Delight' w/ Patio! 1 Mi to Ball State
A hotel lobby with a reception desk, a dining area with round tables and chairs, a kitchen area, and a window with a view.

8. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (152 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveler
$70 nightly
The price is $77
Sep 27 - Sep 28
Total with taxes and fees
King Bed Non-Smoking
A hotel room with two beds, a small table, a mirror, and a bathroom with a sink and toilet.

9. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (116 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveler
$75 nightly
The price is $83
Sep 27 - Sep 28
Total with taxes and fees
2 Queen Beds Non-Smoking
A dining area with a table set for four, chairs, and a patterned wallpaper.

10. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (18 reviews)
"Nice property no hassel stay!"
United States
Donald D.
$255 nightly
The price is $286
Sep 27 - Sep 28
Total with taxes and fees
Retro Home Close to Campus

11. Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Muncie
10.0 out of 10, Exceptional, (8 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
$200 nightly
The price is $224
Oct 20 - Oct 21
Total with taxes and fees
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

12. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (20 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
$279 nightly
The price is $312
Sep 27 - Sep 28
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

13. 'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
$303 nightly
The price is $321
Sep 28 - Sep 29
Total with taxes and fees
'downtown Delight' w/ Patio! 1 Mi to Ball State
A hotel room with two beds, a nightstand with a lamp, and a wall-mounted telephone.

14. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
$59 nightly
The price is $65
Oct 20 - Oct 21
Total with taxes and fees
2 Queen Beds | Non-Smoking
A hallway with wooden flooring, a staircase, and a door at the end.

15. first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen

first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen
Muncie
first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen
A cozy living room with a sofa, a bench, a coffee table, and a patterned rug.

16. Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (19 reviews)
"The house is very clean and nicely appointed. Owner is quick to respond to messages. We would definitely stay here again."
United States
Joanne K.
$173 nightly
The price is $194
Oct 8 - Oct 9
Total with taxes and fees
Boho Bungalow off Main-one block from Lovely Park
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

17. Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Muncie
$214 nightly
The price is $240
Sep 27 - Sep 28
Total with taxes and fees
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

18. Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Fort Recovery
10.0 out of 10, Exceptional, (14 reviews)
"Our family had a great stay! "
United States
todd b.
$405 nightly
The price is $405
Sep 27 - Sep 28
Total with taxes and fees
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

19. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
$280 nightly
The price is $314
Oct 1 - Oct 2
Total with taxes and fees
Westcott Mansion with Pickleball Court & Huge Gazebo

20. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
10.0 out of 10, Exceptional, (1 review)
"Stay was awesome. House was so clean and host was awesome."
United States
Sharon C.
$188 nightly
The price is $211
Oct 26 - Oct 27
Total with taxes and fees
Cozy 2-bedroom next to Cardinal Greenway Trail
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

Comfort Suites Richmond East

Comfort Suites Richmond East

10/10 Excellent
"everything about this hotel was perfect. everything was clean breakfast was exceptional. would definitely stay here again."
Audrey 1-night trip
Posted 2 days ago
Comfort Suites Richmond East

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $77 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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

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?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: 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.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and Mansfield Park are a couple of picturesque spots to get outside and enjoy nature. Winchester Speedway and Winchester Golf Club 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.