Winchester Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Winchester Vacation Homes

Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (20)
"Great stay "
The price is CA $138
CA $247 total
includes taxes & fees
Aug 25 - Aug 26
Cardinal Cottage - 2 bedroom cozy home
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, (194)
"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.

9.0 out of 10, Wonderful, (10)
"Nice, quiet, peaceful."
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Retro Home Close to Campus
Dining

Retro Home Close to Campus

9.8 out of 10, Exceptional, (6)
The price is CA $186
CA $407 total
includes taxes & fees
Aug 17 - Aug 18
Retro Home Close to Campus
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, (37)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!
Charming 3-bedroom house with AC, WiFi in Greenville
Property grounds

Charming 3-bedroom house with AC, WiFi in Greenville

10.0 out of 10, Exceptional, (2)
"Nice place good location. Would highly recommend to anyone."
The price is CA $216
CA $341 total
includes taxes & fees
Aug 10 - Aug 11
Charming 3-bedroom house with AC, WiFi in Greenville
Pet-Friendly Greenville Home w/ Private Yard
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (21)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard
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, (29)
"Very nice home and I appreciated the small fence yard for my dog."
3 br country home close to town with hot tub
The Red House
Property grounds

The Red House

9.6 out of 10, Exceptional, (18)
"This was our 2nd stay at the red house while in town to visit family. Perfect location and space for our family of four. Friendly communication with the owner. Would happily stay again. Recommend!"
The Red House
5 min walk to BSU Campus - Quiet Neighborhood
Dining

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (67)
"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
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, (191)
"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!
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Interior

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 CA $482
CA $550 total
includes taxes & fees
Aug 12 - Aug 13
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Godstow House, Come and stay awhile!
TV, fireplace

Godstow House, Come and stay awhile!

10.0 out of 10, Exceptional, (3)
"Enjoyed the family time and plenty space to do it all in. Will definitly recommend to others."
Godstow House, Come and stay awhile!
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

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 CA $217
CA $454 total
includes taxes & fees
Aug 11 - Aug 12
Charming Home! Prime Location! Dog-Friendly!
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, (33)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is CA $227
CA $458 total
includes taxes & fees
Aug 11 - Aug 12
Westcott Mansion with Pickleball Court & Huge Gazebo
Boho Bungalow off Main-one block from Lovely Park
Interior

Boho Bungalow off Main-one block from Lovely Park

9.2 out of 10, Wonderful, (9)
"Neighborhood a little blighted. Little house is a great piece of history. Very well maintained, appointed and loved. We were comfortable."
The price is CA $131
CA $247 total
includes taxes & fees
Aug 11 - Aug 12
Boho Bungalow off Main-one block from Lovely Park
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
7.4 out of 10, Good, (3)
"This is a beautiful home with exceptional amenities. Is just about the closest home to the fairgrounds. Does need a gas grill.Thank you for letting us stay!!"
The price is CA $213
CA $338 total
includes taxes & fees
Aug 18 - Aug 19
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
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.

8.6 out of 10, Excellent, (39)
"Great charm and comfortable place to stay. Would definitely stay again."
3-bedroom vacation home 9 minutes from Ball State University in the country.
3 Bedroom House in Fort Recovery
Fridge, microwave, oven, stovetop

3 Bedroom House in Fort Recovery

10.0 out of 10, Exceptional, (21)
"Great!"
3 Bedroom House in Fort Recovery
Summer Specials-Guest favorite! Near IU Hospital & Ball State University
Dining

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

10.0 out of 10, Exceptional, (20)
"Stayed for 6 nights. Every thing was super clean. Communication with host was wonderful. I will totally be disappointed at my next stay in Muncie if I’m unable to book this listing. A great place to stay*****"
Summer Specials-Guest favorite! Near IU 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.
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Top Winchester Hotel Reviews

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN

10/10 Excellent
"Not a fan of the inst1nt eggs"
Randy 1-night trip
Posted 1 day ago
Hampton Inn & Suites Richmond, IN