Winchester Vacation Rentals from ￥12,947: Search Short-Term Rentals

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Our top choices for Winchester vacation rentals

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

Economy

"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...

Payton L.

￥53,037 total

includes taxes & fees

Oct 6 - Oct 7

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

Economy

￥51,533 total

includes taxes & fees

Oct 6 - Oct 7

A kitchen with wooden cabinets, a stainless steel stove, and a refrigerator.

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

Hagerstown

Emily E.

￥24,397 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with stainless steel appliances, wooden cabinets, and a white tiled backsplash.

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

Hagerstown

Tamera

￥25,830 total

includes taxes & fees

Oct 6 - Oct 7

A living room with hardwood flooring, a leather sofa, a mounted TV, and a door leading to a kitchen.

5. Cardinal Cottage - 2 bedroom cozy home

Muncie

Deb H.

￥26,519 total

includes taxes & fees

Oct 17 - Oct 18

A hotel lobby with a reception desk, a dining area with round tables and chairs, a kitchen area, and a window with a view.

6. King Bed Non-Smoking

Richmond IN

Anonymous traveler

￥12,054 total

includes taxes & fees

Oct 6 - Oct 7

A hotel room with two beds, a small table, a mirror, and a bathroom with a sink and toilet.

7. 2 Queen Beds Non-Smoking

Richmond IN

Anonymous traveler

￥12,947 total

includes taxes & fees

Oct 6 - Oct 7

Start your day at the coffee station — Keurig, drip, or French press featuring local coffee (regular and decaf), tea, creamer, sugar and sweetener. We take coffee very seriously!

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

Muncie

Simonne S.

￥35,889 total

includes taxes & fees

Oct 18 - Oct 19

A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

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

Muncie

Stace Y.

￥54,276 total

includes taxes & fees

Oct 6 - Oct 7

A modern living room with a sofa, armchair, and a white spiral staircase.

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

Richmond

Jon and Keri C.

￥35,005 total

includes taxes & fees

Oct 6 - Oct 7

A hotel room with two beds, a nightstand with a lamp, and a wall-mounted telephone.

11. 2 Queen Beds | Non-Smoking

Richmond IN

￥10,164 total

includes taxes & fees

Oct 6 - Oct 7

A cozy living room with a sofa, a bench, a coffee table, and a patterned rug.

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

Richmond

Joanne K.

A dining area with a table set for four, chairs, and a patterned wallpaper.

13. Retro Home Close to Campus

Muncie

Donald D.

￥46,850 total

includes taxes & fees

Oct 6 - Oct 7

A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

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

Richmond

Jason S.

￥52,066 total

includes taxes & fees

Oct 6 - Oct 7

A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

15. Westcott Mansion with Pickleball Court & Huge Gazebo

Richmond

"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."

Debbie

￥52,153 total

includes taxes & fees

Oct 12 - Oct 13

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

Muncie

￥50,656 total

includes taxes & fees

Oct 6 - Oct 7

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

Muncie

￥38,717 total

includes taxes & fees

Oct 6 - Oct 7

A kitchen with a dining area, white cabinets, a refrigerator, and a view of the outdoors.

18. Cozy 2-bedroom next to Cardinal Greenway Trail

Muncie

Sharon C.

￥32,530 total

includes taxes & fees

Nov 2 - Nov 3

A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

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

Fort Recovery

todd b.

￥68,191 total

includes taxes & fees

Oct 11 - Oct 12

A gym with various exercise equipment, large windows, and a view of the outside.

20. 1 QUEEN BED | BUSINESS, NON-SMOKING

Richmond IN

Anonymous traveler

￥10,164 total

includes taxes & fees

Oct 6 - Oct 7

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Top Winchester Hotel Reviews

Comfort Suites Richmond East

10/10 Excellent

"Breakfast was very good with a wide variety of hot and cold foods - biscuits and gravy, eggs, sausage (sausage was not good), make your own waffles, fresh fruits, yogurt, pastries, fruit juices, coffee. Attendant was very responsive to requests to refill low inventory even in the later part of breakfast. Appeared to be sufficient parking. Fresh water available in lobby. Clean rooms. Expedia had better rate than booking via hotel's site. One of very few that doesn't allow pets."

Baymont by Wyndham Richmond I-70

10/10 Excellent

"Clean and quiet. Property was fully booked, so I was expecting at least a little noise bleed from other rooms, but there was none. The room was spacious and comfortable. Was expecting it to be a little dated based on the exterior, but the inside was beautifully updated. Breakfast, while looking and feeling similar to other continentals, was delicious. Most of the time you get dried out, tasteless food that's been out too long. This hotel did not have that issue. Plenty of options, all tasted great. They also had a waffle maker that made 4 small waffles instead of one big one. Random detail, but was just a whimsical cherry on top of the great overall stay. No need to keep weighing options, this is the one!"

Motel 6 Richmond, IN

10/10 Excellent

"I stay here every time I drive from Iowa to visit family in Virginia. It’s great in every other way, but for the life of me I cannot figure out how it is ADA compliant. A person with greater mobility issues than my minor ones simply could not navigate it. It has zero handicap accessibility features."

Find out more about Winchester

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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 Burlington Lake 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.

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Check prices for these dates

Our top choices for Winchester vacation rentals

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

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

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

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

5. Cardinal Cottage - 2 bedroom cozy home

6. King Bed Non-Smoking

7. 2 Queen Beds Non-Smoking

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

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

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

11. 2 Queen Beds | Non-Smoking

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

13. Retro Home Close to Campus

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

15. Westcott Mansion with Pickleball Court & Huge Gazebo

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

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

18. Cozy 2-bedroom next to Cardinal Greenway Trail

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

20. 1 QUEEN BED | BUSINESS, NON-SMOKING

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Comfort Suites Richmond East

Baymont by Wyndham Richmond I-70

Comfort Inn & Suites Muncie Near University

Motel 6 Richmond, IN

Best Western Plus Richmond Indiana I-70

Fairfield Inn by Marriott Muncie

Super 8 by Wyndham Muncie/Ball St. College Area

Randolph Inn and Suites

Quality Inn and Conference Center

Find out more about Winchester

Frequently asked questions

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