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Vacation Homes in Winchester

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

10.0 out of 10, Exceptional, (192)
"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

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

9.8 out of 10, Exceptional, (9)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

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

9.8 out of 10, Exceptional, (188)
"Plenty of room for our 25 that stayed. The pool is wonderful. Very clean and communication is excellent. This was our second stay and will do it again. Thank you Ted"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.6 out of 10, Exceptional, (7)
"It was a great place out away from town but close enough you can make it into Richmond with a 15-20 min easy drive "
Quaint Economy Retreat w/ Patio & Spacious Yard!

Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

7.8 out of 10, Good, (7)
"Good"
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

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

10.0 out of 10, Exceptional, (36)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (65)
"Nice house close to Ball State and other activities. Great communication by the host and easy access into the house. Highly recommend. "
5 min walk to BSU Campus - Quiet Neighborhood

Summer Specials-Guest favorite! Near IU Hospital & Ball State University

10.0 out of 10, Exceptional, (19)
"The house is very clean and comfortably furnished. Hosts were attentive and responsive. I hope to stay there again."
Summer Specials-Guest favorite! Near IU Hospital & Ball State University

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (8)
"We are from Richmond originally and come back to visit family often. Definitely will be back. Great stay, great host, very accommodating, and clean. Highly recommend if you are in the area. "
The price is SAR 591
SAR 1,237 total
includes taxes & fees
28 Jul - 29 Jul
Charming Home! Prime Location! Dog-Friendly!

Cardinal Cottage - 2 bedroom cozy home

9.8 out of 10, Exceptional, (16)
"The property is furnished to a high standard."
The price is SAR 338
SAR 630 total
includes taxes & fees
16 Jul - 17 Jul
Cardinal Cottage - 2 bedroom cozy home

Charming 3-bedroom house with AC, WiFi in Greenville

The price is SAR 589
SAR 930 total
includes taxes & fees
22 Jul - 23 Jul
Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

2.0 star property
6.0 out of 10, (2)
"Didn’t get in the house"
The price is SAR 581
SAR 922 total
includes taxes & fees
22 Jul - 23 Jul
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Retro Home Close to Campus

9.6 out of 10, Exceptional, (5)
The price is SAR 506
SAR 1,113 total
includes taxes & fees
26 Jul - 27 Jul
Retro Home Close to Campus

Boho Bungalow off Main-one block from Lovely Park

9.4 out of 10, Exceptional, (8)
"We liked the cleanliness of the property. There is also plenty of things to do and great places to eat with in a short distance of the property"
The price is SAR 521
SAR 857 total
includes taxes & fees
29 Jul - 30 Jul
Boho Bungalow off Main-one block from Lovely Park

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 SAR 1,313
SAR 1,500 total
includes taxes & fees
22 Jul - 23 Jul
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10

Godstow House, Come and stay awhile!

10.0 out of 10, Exceptional, (2)
"Enjoyed the family time and plenty space to do it all in. Will definitly recommend to others."
Godstow House, Come and stay awhile!

Exquisite Hagerstown Home with Deck & Gazebo!

10.0 out of 10, Exceptional, (5)
"This property was fantastic and had all the amenities we were looking for in a long weekend away. "
Exquisite Hagerstown Home with Deck & Gazebo!

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (31)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is SAR 619
SAR 1,248 total
includes taxes & fees
20 Jul - 21 Jul
Westcott Mansion with Pickleball Court & Huge Gazebo

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (20)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard

3-bedroom vacation home 9 minutes from Ball State University in the country.

9.0 out of 10, Wonderful, (36)
"Great charm and comfortable place to stay. Would definitely stay again."
3-bedroom vacation home 9 minutes from Ball State University in the 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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