Search Vacation Homes in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

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, (181)
"Each year our family gathers together from 3 states to spend 4 days together. We plan meals, play games, and spend this time making memories that will last a lifetime. This was a perfect location to spend those 4 days"
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 SAR 672
SAR 766 total
includes taxes & fees
14 May - 15 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, (4)
"Came to Muncie to play a roller derby double header with my teamates from Chicago-Style Roller Derby. The house was perfect for 7 adults. Could orobably fit more comfortably, but we thought it was the perfect space for 7. Would definitely stay here again."
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, (60)
"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
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, (17)
"Very clean, cute, centrally located"
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, (6)
"My husband, daughter and her 3 boys and dog were traveling home from vacation in New York and stayed here overnight. Everything was so comfortable and easy. I would definitely recommend this beautiful home away from home."
The price is SAR 657
SAR 1,324 total
includes taxes & fees
17 Apr - 18 Apr
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)
"In Muncie for Ball State visit. Definitely recommend!"
The price is SAR 375
SAR 673 total
includes taxes & fees
23 Apr - 24 Apr
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

The price is SAR 563
SAR 1,202 total
includes taxes & fees
16 Apr - 17 Apr
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, (29)
"My family (10 people) stayed here for a night. BEAUTIFUL property! Fun to explore the house and grounds. The bedrooms were uniquely designed and the house is a fascinating historic property!! We had some much fun and would definitely come back! "
The price is SAR 619
SAR 1,249 total
includes taxes & fees
16 Apr - 17 Apr
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (181)
"Each year our family gathers together from 3 states to spend 4 days together. We plan meals, play games, and spend this time making memories that will last a lifetime. This was a perfect location to spend those 4 days"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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
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.
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.