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Compare 51 Vacation Homes in Winchester with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (188)
"An awesome place to stay with a large group. The indoor pickleball was a huge hit!!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

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

9.8 out of 10, Exceptional, (182)
"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!

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

9.8 out of 10, Exceptional, (7)
"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.

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

2.0 star property
6.0 out of 10, (2)
"The house exceeded our expectations. Plenty of room, very clean, comfortable beds, comfortable furniture, and a huge TV to watch the game on. There is also a big game room. The host, Matt, was easy to work with and communicated promptly. If you are in the area, don't hesitate to rent this lovely home."
The price is AED 632
AED 973 total
includes taxes & fees
12 May - 13 May
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

The University House King Beds+Fast WIFI+W/D

10.0 out of 10, Exceptional, (6)
"Loved all the space & the fact that it was child friendly!"
The University House King Beds+Fast WIFI+W/D

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (63)
"The house was perfect for what we needed. We were coming and going all week. "
5 min walk to BSU Campus - Quiet Neighborhood

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

9.0 out of 10, Wonderful, (34)
"Had Thanksgiving with the family, lots of room. Love the quiet surroundings "
3-bedroom vacation home 9 minutes from Ball State University in the country.

May/June Specials-Guest favorite-Near IU Health Hospital & Ball State University

10.0 out of 10, Exceptional, (18)
"The house is very clean and comfortably furnished. Hosts were attentive and responsive. I hope to stay there again."
May/June Specials-Guest favorite-Near IU Health Hospital & Ball State University

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (7)
"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 AED 555
AED 1,181 total
includes taxes & fees
2 Jun - 3 Jun
Charming Home! Prime Location! Dog-Friendly!

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (12)
"My wife and I enjoyed staying at this house. It was just what we needed for the night! It was clean, cozy and comfortable. We’d stay here again."
The price is AED 367
AED 658 total
includes taxes & fees
9 May - 10 May
Cardinal Cottage - 2 bedroom cozy home

3 br country home close to town with hot tub

9.4 out of 10, Exceptional, (27)
"Great place, great location, awesome hosts."
3 br country home close to town with hot tub

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

10.0 out of 10, Exceptional, (33)
"We really enjoyed our stay here, what a lovely home. "
Recently remodeled Colonial-style home with room for the whole family!

Retro Home Close to Campus

10.0 out of 10, Exceptional, (1)
Retro Home Close to Campus

Exquisite Hagerstown Home with Deck & Gazebo!

10.0 out of 10, Exceptional, (4)
"This property was fantastic and had all the amenities we were looking for in a long weekend away. "
Exquisite Hagerstown Home with Deck & Gazebo!

3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table

10.0 out of 10, Exceptional, (1)
"Everything was fine except the check in. An incorrect code was given at first (numbers were transposed). Our guests spent a long time trying to enter the property. Eventually when the correct code was sent the guests gained access to the property."
3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table

2 Bedroom Retreat near Earlham College in Richmond IN

10.0 out of 10, Exceptional, (25)
"Will stay there again"
2 Bedroom Retreat near Earlham College in Richmond IN

Westcott Mansion with Pickleball Court & Huge Gazebo

9.8 out of 10, Exceptional, (30)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is AED 606
AED 1,222 total
includes taxes & fees
11 May - 12 May
Westcott Mansion with Pickleball Court & Huge Gazebo

Godstow House, Come and stay awhile!

10.0 out of 10, Exceptional, (2)
"We had a very good time. It exceeded our expectations."
Godstow House, Come and stay awhile!

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

Boho Bungalow off Main-one block from Lovely Park

9.2 out of 10, Wonderful, (7)
"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 AED 349
AED 658 total
includes taxes & fees
12 May - 13 May
Boho Bungalow off Main-one block from Lovely Park
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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Other property types in Winchester

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

9.8 out of 10, Exceptional, (182)
"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!

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (63)
"The house was perfect for what we needed. We were coming and going all week. "
5 min walk to BSU Campus - Quiet Neighborhood

May/June Specials-Guest favorite-Near IU Health Hospital & Ball State University

10.0 out of 10, Exceptional, (18)
"The house is very clean and comfortably furnished. Hosts were attentive and responsive. I hope to stay there again."
May/June Specials-Guest favorite-Near IU Health Hospital & Ball State University
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.