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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winchester vacation rentals

Property grounds

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (8 reviews)
"Thank you we enjoyed the place but we would like to get some more nights if all possible"
United States
Tommy H.
The price is ￥13,062
￥19,845 total
includes taxes & fees
Jul 4 - Jul 5
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
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!!
The Hill
9.8 out of 10, Exceptional, (189 reviews)
"Great location and a cute little bungalow!"
United States
Alicia O.
The price is ￥13,788
￥24,538 total
includes taxes & fees
Jul 5 - Jul 6
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
TV, fireplace, offices

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck
Soulard
9.8 out of 10, Exceptional, (6 reviews)
The price is ￥17,077
￥38,787 total
includes taxes & fees
Jul 14 - Jul 15
Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (51 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
The price is ￥15,965
￥37,477 total
includes taxes & fees
Jul 6 - Jul 7
Top of Geyer apartment
Dining

Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (162 reviews)
"Great location in the Tower Grove area. We would definitely stay again!"
United States
Jeffrey Z.
The price is ￥10,885
￥24,715 total
includes taxes & fees
Jul 5 - Jul 6
Centrally located in the Tower Grove East neighborhood!
Fridge, microwave, oven, stovetop

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (49 reviews)
"Made us feel like we was at home nice place "
United States
Marshay M.
The price is ￥19,190
￥42,595 total
includes taxes & fees
Jul 7 - Jul 8
Convenience 2 Bedroom House to Explore All of St Louis
Interior

Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.0 out of 10, Wonderful, (14 reviews)
"Great place for a short get away"
United States
andytrower U.
Adorable small house - quiet & safe - 2 BR 1 Bath
Exterior

Kid and pet friendly 2 nd floor duplex

Kid and pet friendly 2 nd floor duplex
Pacific
9.0 out of 10, Wonderful, (28 reviews)
"The house was clean and comfortable. Would stay there again."
United States
Jason T.
The price is ￥23,947
￥30,639 total
includes taxes & fees
Jul 5 - Jul 6
Kid and pet friendly 2 nd floor duplex
TV, offices

Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.8 out of 10, Good, (11 reviews)
"We enjoyed our stay"
United States
Dee
The price is ￥13,546
￥33,381 total
includes taxes & fees
Jul 5 - Jul 6
Safe and private apt-Near Forest Park-Free parking
Fridge, microwave, oven, stovetop

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
8.6 out of 10, Excellent, (13 reviews)
"Clean, convenient and satisfied our needs for this stay. "
United States
Michael L.
The price is ￥8,869
￥45,309 total
includes taxes & fees
Jul 14 - Jul 15
Settle into Soulard! 6 beds 2 full baths!
Fridge, microwave, oven, stovetop

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony
The Gate
8.4 out of 10, Very Good, (12 reviews)
"Best host I have ever stayed with. Would happily stay at another Synergy property. "
United States
Ceili H.
The price is ￥13,884
￥29,784 total
includes taxes & fees
Jul 6 - Jul 7
Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony
Interior

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.4 out of 10, Exceptional, (23 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
Elegant Minimalist Gem w/ Private backyard, W/D
Interior

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (65 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
The price is ￥15,965
￥33,987 total
includes taxes & fees
Jul 6 - Jul 7
Cozy Soulard 2BR w/ Free Parking
Interior

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic place!"
United States
Anonymous traveler
The price is ￥15,520
￥18,002 total
includes taxes & fees
Jul 13 - Jul 14
2 Queen Beds | Non-Smoking, Kitchen
TV, offices

Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.2 out of 10, Wonderful, (20 reviews)
"Great location. Long term stay was excellent!"
United States
Shay W.
The price is ￥7,982
￥27,456 total
includes taxes & fees
Jul 6 - Jul 7
Charming Tower Grove Flat-Steps to T.G Park+Grand
Fridge, microwave, oven, coffee/tea maker

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Beatiful home close to venues and shops. "
United States
Kelly H.
The price is ￥15,320
￥31,943 total
includes taxes & fees
Jul 14 - Jul 15
Stylish South City King 1BR Apt
Smart TV, fireplace, books

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Bevo Mill
9.0 out of 10, Wonderful, (31 reviews)
"Well supplied, responsive host, great location! "
United States
Christine C.
The price is ￥19,190
￥37,299 total
includes taxes & fees
Jul 15 - Jul 16
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Fridge, microwave, oven, stovetop

Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (77 reviews)
"This was a great place to stay. Everything was just as pictured and wonderfully stocked with every amenity. The host responded quickly with answers. Would stay here again."
United States
Amy S.
The price is ￥20,964
￥43,058 total
includes taxes & fees
Jul 14 - Jul 15
Classy Midtown 2BR, King Master
Fridge, microwave, oven, stovetop

Historic 1908 Frenchtown Home

Historic 1908 Frenchtown Home
St. Charles Historic District
8.6 out of 10, Excellent, (23 reviews)
"yes the kitchen was fully equipped."
Canada
David M.
The price is ￥22,293
￥53,855 total
includes taxes & fees
Jul 5 - Jul 6
Historic 1908 Frenchtown Home
Interior

Spacious, cozy home in Saint Louis

Spacious, cozy home in Saint Louis
St. Louis
10.0 out of 10, Exceptional, (37 reviews)
"The house was amazing and comfortable. Our host was very good communicating with all questions we had. "
United States
Misty B.
The price is ￥31,446
￥50,296 total
includes taxes & fees
Jul 6 - Jul 7
Spacious, cozy home in Saint Louis
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

Pear Tree Inn St. Louis Near Union Station

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent
"A/C was not working the first day, but one mention to the staff and it was fixed by the time we returned to the room at the end of the day. Site was clean, staff friendly and helpful, and we loved the drinks and snacks!"
Daniel 3-night trip
Posted 4 hours ago
Pear Tree Inn St. Louis Near Union Station

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals where you'll be just 13.2 mi (21.2 km) from St. Louis Zoo, providing a more remote option if you want peace and quiet.

What's the top vacation rental in Winchester?

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck: This vacation home rental outside of Winchester offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like St. Louis Zoo, or get outside and enjoy nature at Forest Park. In the larger area, you’ll find Castlewood State Park and Bellerive Country Club.

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.