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

Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
Exterior

Charming 3-bedroom house with WiFi, AC in the heart of St. Louis

2.0 star property
8.2 out of 10, Very good, (20)
"This was a great location. Perfect for our small group of friends. Very clean, easy check in. Very old house but done well. Would recommend. "
The price is CA $148
CA $430 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Dining

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

9.6 out of 10, Exceptional, (45)
"Lovely stay, very sweet house in a cute neighborhood. Great for traveling with kids! Thank you!"
The price is CA $197
CA $474 total
includes taxes & fees
Sep 1 - Sep 2
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Stunning 1890's Home - Sleeps 8!
Microwave, oven, stovetop, dishwasher

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (75)
"The house is beautiful, in a great location, and has all the amenities of home. Definitely glad we stayed here instead of a nearby hotel."
The price is CA $236
CA $516 total
includes taxes & fees
Sep 2 - Sep 3
Stunning 1890's Home - Sleeps 8!
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Fridge, microwave, oven, stovetop

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

9.8 out of 10, Exceptional, (148)
"This was a gem! So glad I booked this property and would highly recommend to any friends or family."
The price is CA $117
CA $197 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Centrally located in the Tower Grove East neighborhood!
Interior

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (125)
"Thoroughly enjoyed staying here. My sister and I were in town for an event and staying here made it even more fun!"
The price is CA $102
CA $230 total
includes taxes & fees
Sep 2 - Sep 3
Centrally located in the Tower Grove East neighborhood!
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Fridge, microwave, oven, stovetop

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

10.0 out of 10, Exceptional, (90)
"We enjoyed our one night stay here. There's plenty of space and lots of historic character. Everything was as described and our check in and out process was simple."
The price is CA $165
CA $306 total
includes taxes & fees
Sep 2 - Sep 3
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Modern House with Terrace Near Forest Park
Property grounds

Modern House with Terrace Near Forest Park

9.0 out of 10, Wonderful, (11)
"This was perfect for 6. Close to a park with short running loop. Quaint shops with restaurants nearby. Would definitely stay here again!"
Modern House with Terrace Near Forest Park
Entire Dogtown House near Zoo, Forest Park and Wash U
Exterior

Entire Dogtown House near Zoo, Forest Park and Wash U

10.0 out of 10, Exceptional, (211)
"Great place to stay. Quiet area and close to activities. "
Entire Dogtown House near Zoo, Forest Park and Wash U
AK's STL Pearl Grey House - Game Room
Fridge, microwave, oven, stovetop

AK's STL Pearl Grey House - Game Room

9.0 out of 10, Wonderful, (7)
"Quiet neighborhood, comfortable house, well-stocked kitchen. We would stay here again."
The price is CA $283
CA $638 total
includes taxes & fees
Sep 1 - Sep 2
AK's STL Pearl Grey House - Game Room
Convenience 2 Bedroom House to Explore All of St Louis
Fridge, microwave, stovetop, coffee/tea maker

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (27)
"One night stay. Location convenient to downtown Clayton. "
The price is CA $146
CA $291 total
includes taxes & fees
Sep 1 - Sep 2
Convenience 2 Bedroom House to Explore All of St Louis
St. Charles 1860's Gem - Sleeps 6!
Fridge, microwave, oven, stovetop

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (119)
"Everything was great!"
The price is CA $151
CA $328 total
includes taxes & fees
Sep 2 - Sep 3
St. Charles 1860's Gem - Sleeps 6!
Madison House 1 -Walk to Main St
2 bedrooms, desk, iron/ironing board, travel crib

Madison House 1 -Walk to Main St

9.0 out of 10, Wonderful, (11)
"Comfy fun stay!"
The price is CA $122
CA $324 total
includes taxes & fees
Sep 1 - Sep 2
Madison House 1 -Walk to Main St
Tamm Ave 3-BR Retreat
Dining

Tamm Ave 3-BR Retreat

9.6 out of 10, Exceptional, (40)
"Great location for the stuff we did. We did have to finish the towels and some sheets that were left in the washer and dryer wet "
Tamm Ave 3-BR Retreat
Honky Tonk Hideaway
Outdoor dining

Honky Tonk Hideaway

9.2 out of 10, Wonderful, (5)
"Great place to stay"
Honky Tonk Hideaway
Residence on the Roundabout
Interior

Residence on the Roundabout

9.6 out of 10, Exceptional, (135)
"We loved it. Had everything we needed and more. Very clean and comfortable "
Residence on the Roundabout
The Lewis & Clark Hangout
Fridge, microwave, oven, stovetop

The Lewis & Clark Hangout

9.0 out of 10, Wonderful, (17)
"Enjoyed are stay"
The price is CA $302
CA $643 total
includes taxes & fees
Sep 1 - Sep 2
The Lewis & Clark Hangout
Brand New! Soulard Charmer - Pet Friendly.
Terrace/patio

Brand New! Soulard Charmer - Pet Friendly.

9.6 out of 10, Exceptional, (20)
"Jackson was very responsive pre visit as well as check-in and checkout Comfortable for 6 of us and the cooking and parking was easy. Convenient location to downtown St Louis as well as highways and airport"
The price is CA $179
CA $362 total
includes taxes & fees
Sep 2 - Sep 3
Brand New! Soulard Charmer - Pet Friendly.
The White House in St. Louis
Terrace/patio

The White House in St. Louis

9.0 out of 10, Wonderful, (17)
"3 day trip to St. Louis with our family of four. It was a great place to stay and had room for all! Loved the huge backyard too!"
The White House in St. Louis
The Hill | 4 Bed 2 Bath | Beautiful Private Home
Exterior

The Hill | 4 Bed 2 Bath | Beautiful Private Home

9.8 out of 10, Exceptional, (53)
"The home is in a really cool part of town called the Hill. The house is old school brown stone, with original wood and stained glass. It was clean, nicely furnished and very comfortable. I will make an effort to stay again when I’m in town. "
The Hill | 4 Bed 2 Bath | Beautiful Private Home
Unique, Homey, & Spacious City Nest
Interior

Unique, Homey, & Spacious City Nest

9.4 out of 10, Exceptional, (16)
"Enjoyed the property for our short trip to visit family."
Unique, Homey, & Spacious City Nest
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

Find out more about Winchester

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
Accommodation
545 Vacation Homes
Lowest Price
CA $102
Highest Price
CA $302

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