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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester vacation rentals

Interior

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is AED 397
AED 1,199 total
includes taxes & fees
11 Oct - 12 Oct
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Living area

2. 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.
The price is AED 283
AED 1,234 total
includes taxes & fees
14 Oct - 15 Oct
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A kitchen with wooden cabinets, a stainless steel stove, and a refrigerator.

3. 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.
The price is AED 245
AED 541 total
includes taxes & fees
20 Oct - 21 Oct
New Hagerstown Apartment - Self Check-in. Sleeps 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+

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
The price is AED 290
AED 634 total
includes taxes & fees
26 Oct - 27 Oct
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
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

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (47 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is AED 367
AED 658 total
includes taxes & fees
1 Nov - 2 Nov
Cardinal Cottage - 2 bedroom cozy home
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

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
The price is AED 236
AED 298 total
includes taxes & fees
6 Nov - 7 Nov
King Bed Non-Smoking
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
9.8 out of 10, Exceptional, (28 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is AED 404
AED 1,209 total
includes taxes & fees
8 Oct - 9 Oct
'Downtown Delight' w/ Patio! 1 Mi to Ball State
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

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.
The price is AED 437
AED 884 total
includes taxes & fees
3 Nov - 4 Nov
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
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, (117 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveler
The price is AED 236
AED 301 total
includes taxes & fees
22 Oct - 23 Oct
2 Queen Beds Non-Smoking
A hotel room with two beds, a nightstand with a lamp, and a wall-mounted telephone.

10. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 223
AED 247 total
includes taxes & fees
6 Nov - 7 Nov
2 Queen Beds | Non-Smoking
A dining area with a table set for four, chairs, and a patterned wallpaper.

11. 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.
The price is AED 496
AED 1,090 total
includes taxes & fees
8 Oct - 9 Oct
Retro Home Close to Campus
A modern living room with a sofa, armchair, and a white spiral staircase.

12. 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.
The price is AED 422
AED 810 total
includes taxes & fees
4 Nov - 5 Nov
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.

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

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is AED 580
AED 1,212 total
includes taxes & fees
5 Nov - 6 Nov
'downtown Delight' w/ Patio! 1 Mi to Ball State
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

14. 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.
The price is AED 1,388
AED 1,587 total
includes taxes & fees
11 Oct - 12 Oct
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.

15. 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
The price is AED 606
AED 1,222 total
includes taxes & fees
12 Oct - 13 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

16. 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.
The price is AED 579
AED 1,207 total
includes taxes & fees
8 Oct - 9 Oct
Charming Home! Prime Location! Dog-Friendly!
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
The price is AED 584
AED 901 total
includes taxes & fees
8 Oct - 9 Oct
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A gym with various exercise equipment, large windows, and a view of the outside.

18. 1 QUEEN BED | BUSINESS, NON-SMOKING

1 QUEEN BED | BUSINESS, NON-SMOKING
Richmond IN
10.0 out of 10, Exceptional, (4 reviews)
"Would book again without hesitation if passing through Charlotte. Easy access, comfy bed, quick snack options kept it simple and good."
United States
Anonymous traveler
The price is AED 223
AED 247 total
includes taxes & fees
6 Nov - 7 Nov
1 QUEEN BED | BUSINESS, NON-SMOKING
A hallway with vending machines and a staircase.

19. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (2 reviews)
"Evenings spent by the pool were very relaxing, perfect way to unwind after busy days."
United States
Anonymous traveler
The price is AED 223
AED 247 total
includes taxes & fees
6 Nov - 7 Nov
1 King Bed | Non-Smoking
A kitchen with a dining area, white cabinets, a refrigerator, and a view of the outdoors.

20. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
10.0 out of 10, Exceptional, (2 reviews)
"Stay was awesome. House was so clean and host was awesome."
United States
Sharon C.
The price is AED 419
AED 757 total
includes taxes & fees
2 Nov - 3 Nov
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

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

10/10 Excellent
"My first impression was the lady working the evening shift. I have never had such a warm welcome at a hotel, ever. The hotel isn't fancy but it was well maintained, clean and had a nice breakfast. I like that the morning desk clerk genuinely asked about my stay. I hesitantly mentioned a minor problem with the blackout curtains and it seemed like he really cared and would look into it. They are very conveniently located to the freeway and restaurants, I would stay again."
Catherine 1-night trip
Posted 18 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?

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.