Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Browse Select Winchester Vacation Homes

Our top choices for Winchester vacation homes

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Terrace/patio

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (78)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Fridge, microwave, oven, stovetop

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

9.8 out of 10, Exceptional, (53)
"House was clean with lots of stuff to do! Very quiet get away"
The price is CA $137
CA $174 total
includes taxes & fees
Sep 1 - Sep 2
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Home with great location
Exterior

Home with great location

10.0 out of 10, Exceptional, (20)
"Great stay for our family - thank you!"
Home with great location
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Dining

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (55)
"We enjoyed our stay at this beautiful country home. "
The price is CA $248
CA $299 total
includes taxes & fees
Aug 27 - Aug 28
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Spacious 6-bedroom house in rural Versailles with many amenities included.
Exterior

Spacious 6-bedroom house in rural Versailles with many amenities included.

10.0 out of 10, Exceptional, (1)
"We stayed for our Mendota FFA Chapter Officer Retreat. It was very accommodating for our group of nine high school students and two adult chaperones. The house itself is a bit chopped up, but has a lot of charm and many unique decor elements. The bar/kitchen was very unique. We utilized both outdoor grill and firepit area to prepare evening meals. The pool table in the basement was a big hit with the boys. Air fresheners were a little overpowering. "
Spacious 6-bedroom house in rural Versailles with many amenities included.
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, bed sheets

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"Wonder!! House and lake amazing! Kitchen well stocked with everything one would need! So many outside adventures! We had a wonderful time. Thank you. "
Idyllic Mt Sterling Retreat w/ Private Lake!
Country Retreat in the heart of Pike County Illinois
Interior

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois
Cozy 3 bedroom family friendly home in pike county IL
Exterior

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (3)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"There is a strong odor of humidity in the hallway and the rooms."
Jacqueline 1-night trip
Posted 2 days ago
Best Western Jacksonville Inn

Find out more about Winchester

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
209
Accommodation
8 Vacation Homes
Lowest Price
CA $137
Highest Price
CA $248

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