Winchester Vacation Rentals

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Nov 2 - Nov 3
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Nov 3 - Nov 4
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Nov 14 - Nov 16

Vacation Rentals in Winchester

Comfort Apartment | 1 bedroom, individually decorated, individually furnished, desk
White House at Grand Central
White House at Grand Central
4.0 star property
8.4 out of 10, Very Good, (122)
"It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay. "
United States
Sharon
The price is ￥11,950
￥23,876 total
includes taxes & fees
Nov 4 - Nov 5
White House at Grand Central
Outdoor dining
Cafe Terrace at TG Park | Fenced Backyard+W/D
Cafe Terrace at TG Park | Fenced Backyard+W/D
2.0 star property
9.4 out of 10, Exceptional, (6)
"We rented this property because it was convenient to our son's home, which is directly across Tower Grove Park. The one bedroom layout was perfect, and the lodging was exceptionally clean. I highly recommend this VRBO."
United States
Bob K.
The price is ￥7,546
￥26,128 total
includes taxes & fees
Nov 4 - Nov 5
Cafe Terrace at TG Park | Fenced Backyard+W/D
Fridge, microwave, oven, stovetop
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (152)
"Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing "
United States
Lindsay
The price is ￥11,780
￥20,662 total
includes taxes & fees
Nov 5 - Nov 6
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Fridge, microwave, oven, coffee/tea maker
Stylish South City King 1BR Apt
Stylish South City King 1BR Apt
2.0 star property
10.0 out of 10, Exceptional, (8)
"Comfy, cozy, and cute"
United States
Healing with N.
The price is ￥12,011
￥27,288 total
includes taxes & fees
Nov 11 - Nov 12
Stylish South City King 1BR Apt
Interior
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park
2.0 star property
10.0 out of 10, Exceptional, (8)
"My friends and I really enjoyed how close it was to the loop and how clean the place is."
United States
David M.
The price is ￥22,175
￥54,735 total
includes taxes & fees
Nov 4 - Nov 5
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park
Fridge, microwave, oven, stovetop
Classy Midtown 3BR, King Master
Classy Midtown 3BR, King Master
10.0 out of 10, Exceptional, (58)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
The price is ￥12,935
￥31,910 total
includes taxes & fees
Nov 11 - Nov 12
Classy Midtown 3BR, King Master
House (2 Bedrooms) | Interior
14 Mi to St Louis: Dog-friendly Columbia Home
14 Mi to St Louis: Dog-friendly Columbia Home
3.0 star property
14 Mi to St Louis: Dog-friendly Columbia Home
Fridge, microwave, oven, stovetop
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
10.0 out of 10, Exceptional, (97)
"We had a wonderful time! Great comfortable house in easy access of St. Louis activities. "
United States
Rebekah S.
The price is ￥18,479
￥35,110 total
includes taxes & fees
Nov 9 - Nov 10
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Fridge, microwave, oven, stovetop
Elegant Minimalist Gem w/ Private backyard, W/D
Elegant Minimalist Gem w/ Private backyard, W/D
9.2 out of 10, Wonderful, (16)
"This was our second stay and everything was great! The place has everything you would have back at home.We walked to local restaurants and enjoyed looking at the decorations on the neighborhood homes. "
United States
- P.
The price is ￥10,625
￥29,729 total
includes taxes & fees
Nov 5 - Nov 6
Elegant Minimalist Gem w/ Private backyard, W/D
Interior
Top of Geyer apartment
Top of Geyer apartment
9.8 out of 10, Exceptional, (40)
"This place was great! I loved the location and Bonnie recommended a bunch of awesome places to eat within walking distance. We will definitely be booking another stay in the future!"
United States
Alena G.
The price is ￥11,780
￥29,027 total
includes taxes & fees
Nov 5 - Nov 6
Top of Geyer apartment
2 bedrooms, iron/ironing board, travel crib, free WiFi
Spacious & Centrally Located Apt (Sleeps 8)
Spacious & Centrally Located Apt (Sleeps 8)
9.8 out of 10, Exceptional, (18)
"It was very clean. Owner was very pleasant and polite. Kids enjoyed their stay. Wonderful experience! Definitely will stay again."
United States
Angela B.
The price is ￥12,319
￥31,189 total
includes taxes & fees
Nov 11 - Nov 12
Spacious & Centrally Located Apt (Sleeps 8)
Fridge, microwave, oven, stovetop
Historic 4‑BR Farmhouse • Steps to Main Street
Historic 4‑BR Farmhouse • Steps to Main Street
10.0 out of 10, Exceptional, (16)
"Our son was married this past weekend. We chose this house based on proximity to the church, rehearsal dinner, other out of town guests and the wedding venue. Over nights were just right to accommodate our multigenerational family, a bedroom on first floor alleviated my parents from using the stairs. We did need to send guests through the down stairs bedroom to access the only first floor bathroom. Kitchen was well appointed, I cooked breakfast, lunch and dinner for our family, amd had some...
United States
Dean B.
The price is ￥14,937
￥74,604 total
includes taxes & fees
Nov 4 - Nov 5
Historic 4‑BR Farmhouse • Steps to Main Street
Fridge, microwave, oven, stovetop
Casa de Saint Charles
Casa de Saint Charles
9.2 out of 10, Wonderful, (17)
"Every thing it said it was, nice place. Beds was very firm. At least the master bed was and one downstairs was my son-in-law said. Very spacious and comfortable "
United States
Dan K.
The price is ￥17,709
￥45,581 total
includes taxes & fees
Nov 4 - Nov 5
Casa de Saint Charles
TV
1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch
1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch
2.0 star property
6.0 out of 10, (3)
"WILL CHARGE ADDITIONAL SECURITY DEPOSIT NOT LISTED ON VRBO. This is charged by sending tenants to a company portal, where check-in instructions are contingent upon paying ADDITIONAL UNLISTED FEE(or 40 dollar non-refundable damage coverage)Decent space. Pretty. Kind of sparse as far as furniture/decor but not bad. I liked the vibe overall. Could use some fixing up but decent for an historic building. NOT SUFFICIENT FOR LONG TERM STAY. Short term might be ok.Not very stocked as far as kitchen,...
United States
Devin L.
1BR Apartment – Washer/Dryer, Fenced Backyard, Free Parking, Near Arch
Fridge, microwave, oven, stovetop
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
9.8 out of 10, Exceptional, (45)
"We had a terrific time in St Louis!! The house was in a perfect location for us!! It was great!! Lots of great places to eat close by. Joe was wonderful and the place was excellent!! "
Canada
Shirley M.
The price is ￥15,553
￥35,476 total
includes taxes & fees
Nov 12 - Nov 13
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Dining
Charming Tower Grove Flat-Steps to T.G Park+Grand
Charming Tower Grove Flat-Steps to T.G Park+Grand
9.8 out of 10, Exceptional, (11)
"My partner and I had a fantastic stay! The unit was very clean and organized. The location is phenomenal for getting around the area and the parking spot is a total plus! The host did a great job communicated with us and helping with anything that came up. Overall we could not have asked for a better stay and would recommend this unit to everyone!"
United States
Caden S.
The price is ￥7,546
￥26,128 total
includes taxes & fees
Nov 4 - Nov 5
Charming Tower Grove Flat-Steps to T.G Park+Grand
Private kitchen
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1
9.0 out of 10, Wonderful, (10)
"Great property!!"
United States
Nicole S.
The price is ￥18,325
￥43,219 total
includes taxes & fees
Nov 4 - Nov 5
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1
Fridge, microwave, oven, stovetop
Convenience 2 Bedroom House to Explore All of St Louis
Convenience 2 Bedroom House to Explore All of St Louis
9.8 out of 10, Exceptional, (36)
"Great spot! We would stay again."
United States
Heather P.
The price is ￥18,171
￥40,761 total
includes taxes & fees
Nov 4 - Nov 5
Convenience 2 Bedroom House to Explore All of St Louis
Dining
Cute town house with fenced backyard
Cute town house with fenced backyard
9.6 out of 10, Exceptional, (17)
"We had a great stay! Thank you! "
United States
Lenae C.
The price is ￥16,160
￥41,019 total
includes taxes & fees
Nov 8 - Nov 9
Cute town house with fenced backyard
Fridge, microwave, oven, stovetop
Cute ranch house -quiet & safe -3 BR 1 Bath
Cute ranch house -quiet & safe -3 BR 1 Bath
9.8 out of 10, Exceptional, (21)
"Great family get away. Close to activities, but far enough away to have a rural feel."
United States
Marvin H.
The price is ￥16,939
￥34,474 total
includes taxes & fees
Nov 4 - Nov 5
Cute ranch house -quiet & safe -3 BR 1 Bath
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

Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

10/10 Excellent
"The room was amazing. The staff was wonderful. Food was ok."
Hillary 2-night trip
Posted 6 hours ago
Hollywood Casino & Hotel St. Louis

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to the most popular local attractions in Winchester, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Winchester?

Madison House 2 -Walk to Main St: This vacation home rental outside of Winchester is equipped with an arcade game room, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Magic House - St. Louis Children's Museum, or get outside and enjoy nature at Lou Fusz Soccer Complex. In the larger area, you’ll find Museum of Transportation and The Factory.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Winchester. Vacation rentals offer amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.