Holiday Homes in Winchester

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Winchester

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, (195)
"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
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.
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
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, (192)
"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!
5 min walk to BSU Campus - Quiet Neighborhood
Dining

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (69)
"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
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, (2)
"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 AU$624
includes taxes & fees
26 Aug - 27 Aug
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Retro Home Close to Campus
Dining

Retro Home Close to Campus

9.8 out of 10, Exceptional, (6)
"Cute home, a lot of unique features. Great location. Owner was very easy to work with and accommodating to our group. Would totally rent this again ."
The price is AU$432
includes taxes & fees
25 Aug - 26 Aug
Retro Home Close to Campus
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (9)
"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 AU$514
includes taxes & fees
25 Aug - 26 Aug
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, (20)
"Great stay "
The price is AU$262
includes taxes & fees
25 Aug - 26 Aug
Cardinal Cottage - 2 bedroom cozy home
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 AU$395
includes taxes & fees
28 Aug - 29 Aug
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
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 AU$387
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house with AC, WiFi in Greenville
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, (22)
"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
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!
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 AU$279
includes taxes & fees
25 Aug - 26 Aug
Boho Bungalow off Main-one block from Lovely Park
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)
"We had a nice time celebrating my sons graduation from Earlham college. There was plenty of room for everyone to have their own bedroom. Very unique property with very nice furnishings. A historic property. We had everything we needed for our stay. Definitely would recommend."
The price is AU$518
includes taxes & fees
25 Aug - 26 Aug
Westcott Mansion with Pickleball Court & Huge Gazebo
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
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
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

Comfort Suites

Comfort Suites

10/10 Excellent
"Great hotel and staff. Very accommodating. Lovely hotel. Would stay again. Enjoyed the fire tables. "
Mike 4-night trip
Posted 20 hours ago
Comfort Suites