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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

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

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

10.0 out of 10, Exceptional, (185)
"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
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Outdoor dining

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

9.8 out of 10, Exceptional, (182)
"We had a great stay! Ted was very communicative and thoughtful of our needs. The house fit our group perfectly and was so much fun. We enjoyed the games onsite and the indoor pool. We were able to visit and relax. A perfect weekend getaway! "
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.
Living area

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

9.8 out of 10, Exceptional, (7)
"The house was just as describedThe host was great and quickly responded with when i had questions. We arrived to find a nice note and home baked cookies. The berries was great and it was very spacious for our large group. Definitely recommend"
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.
Exterior

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 966 total
includes taxes & fees
5 May - 6 May
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
The University House King Beds+Fast WIFI+W/D
Exterior

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

10.0 out of 10, Exceptional, (5)
"Well done start to finish. "
The University House King Beds+Fast WIFI+W/D
5 min walk to BSU Campus - Quiet Neighborhood
Property grounds

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (62)
"We're in town for a sporting event and stayed in this property. Excellent on all accounts and would definitely stay here again. "
5 min walk to BSU Campus - Quiet Neighborhood
3-bedroom vacation home 9 minutes from Ball State University in the country.
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (34)
"House met all our expectations. Very clean. Beautiful property. Short drive on county roads to Ball State University. Could have had some better towels. Perfect layout. "
3-bedroom vacation home 9 minutes from Ball State University in the country.
Spring Specials-Guest favorite-Close to IU Health Hospital&Ball State University
Dining

Spring Specials-Guest favorite-Close to IU Health Hospital&Ball State University

10.0 out of 10, Exceptional, (18)
"One of the reasywe book houses vs hotels is to save money by .making some of our meals. Usually I have to be sure to bring all my cooking utensils and such not just condiments and spices We forgot somethings, measuring spoons and cups. Figures wed have to buy.Was pleasantly surprised to find not only those put other kitchen gadgets as well.And the house was neat and clean. Just the perfect size for 2 couples."
Spring Specials-Guest favorite-Close to IU Health Hospital&Ball State University
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (7)
"Loved the old charm of this property. Was a slight inconvenience being woke up 2 times in the middle of the night by water intrusion alarms in the basement but the owner was prompt the next day to get this handled. Second night slept like a baby and was great to have so many amenities to use to stay in and cook opposed to having more cost to eat out. The owner made sure to represent the property well, and set you up for success letting you know with pets there is no fenced area. Will definitely...
The price is AED 496
AED 1,082 total
includes taxes & fees
5 May - 6 May
Charming Home! Prime Location! Dog-Friendly!
Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (11)
"The property is furnished to a high standard."
The price is AED 367
AED 658 total
includes taxes & fees
1 May - 2 May
Cardinal Cottage - 2 bedroom cozy home
3 br country home close to town with hot tub
Fridge, microwave, oven, stovetop

3 br country home close to town with hot tub

9.4 out of 10, Exceptional, (27)
"This property was perfect for our time with family. "
3 br country home close to town with hot tub
Recently remodeled Colonial-style home with room for the whole family!
Exterior

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

10.0 out of 10, Exceptional, (33)
"The house was exactly an exactly stated and accommodated our group of eight perfectly. Communication with the owner and his responses were spot on. They definitely stay there again. House has a nice vibe to it."
Recently remodeled Colonial-style home with room for the whole family!
Retro Home Close to Campus
Smart TV, fireplace, books

Retro Home Close to Campus

10.0 out of 10, Exceptional, (1)
The price is AED 551
AED 1,172 total
includes taxes & fees
5 May - 6 May
Retro Home Close to Campus
Exquisite Hagerstown Home with Deck & Gazebo!
Property grounds

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!
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Cookware/dishes/utensils

Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

10.0 out of 10, Exceptional, (5)
"Nice quiet location more in the country. Just what we were looking for during a family visit "
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table
Outdoor dining

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
Outdoor dining

2 Bedroom Retreat near Earlham College in Richmond IN

10.0 out of 10, Exceptional, (25)
"We loved the home along with all of the amenities. If your contemplating on which house to stay in choose this one! Cindy provided so many extras! From blankets, towels, kitchen dishes to seasonings & even the basic “staples” in the refrigerator along w snacks. Very beautiful home with character . Thankyou opening your home up to us . We will return! "
2 Bedroom Retreat near Earlham College in Richmond IN
Westcott Mansion with Pickleball Court & Huge Gazebo
8 bedrooms, WiFi, bed sheets

Westcott Mansion with Pickleball Court & Huge Gazebo

9.8 out of 10, Exceptional, (30)
"This home was the perfect place for a weekend bowling getaway with the girls! The property is absolutely beautiful and very well maintained. "
The price is AED 606
AED 1,222 total
includes taxes & fees
1 May - 2 May
Westcott Mansion with Pickleball Court & Huge Gazebo
Godstow House, Come and stay awhile!
TV, fireplace

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
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (20)
"The house was as we expected. Very well decorated and very clean. We felt safe and comfortable. "
Pet-Friendly Greenville Home w/ Private Yard
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!
Outdoor dining

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

9.8 out of 10, Exceptional, (182)
"We had a great stay! Ted was very communicative and thoughtful of our needs. The house fit our group perfectly and was so much fun. We enjoyed the games onsite and the indoor pool. We were able to visit and relax. A perfect weekend getaway! "
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
lake front 2 br condo close to bsu
Exterior

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (42)
"Clean condo in a nice neighborhood. Decorated nicely. Enjoyed our stay. Convenient to many stores and resturants"
lake front 2 br condo close to bsu
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Sport court

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

10.0 out of 10, Exceptional, (185)
"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
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.