Winchester Holiday Rentals

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Holiday Rentals in Winchester

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

2.0 star property
7.8 out of 10, Good, (18)
"The property was quiet and as expected. They were incredibly responsive and helpful with everything. "
The price is NZ$229
includes taxes & fees
17 July - 18 July
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (113)
"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. "
White House at Grand Central

Ballpark Apartments by Barsala

4.0 star property
7.4 out of 10, Good, (9)
"It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot."
Ballpark Apartments by Barsala

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (114)
"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 NZ$273
includes taxes & fees
14 July - 15 July
Centrally located in the Tower Grove East neighborhood!

Funky mini loft in fox park! Pet friendly!!

7.6 out of 10, Good, (74)
"Funky and fun place."
The price is NZ$249
includes taxes & fees
20 July - 21 July
Funky mini loft in fox park! Pet friendly!!

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (18)
"Lovely home. Perfect location and very clean. They left water and fruit for us. That was very thoughtful. Definitely recommend this house. "
The price is NZ$426
includes taxes & fees
20 July - 21 July
Convenience 2 Bedroom House to Explore All of St Louis

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (66)
"Beautiful house and location."
The price is NZ$669
includes taxes & fees
17 July - 18 July
Stunning 1890's Home - Sleeps 8!

StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

10.0 out of 10, Exceptional, (272)
"This was a great location. Cozy, quiet & clean. "
The price is NZ$265
includes taxes & fees
16 July - 17 July
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

NEW Modern & Luxurious 4BDR House. Sleep 12. Minutes to Top Golf and downtown

9.8 out of 10, Exceptional, (30)
"Great stay for our family!!!"
NEW Modern & Luxurious 4BDR House. Sleep 12. Minutes to Top Golf and downtown

Beautiful, Rehabbed Unit in Shaw Community 4228a

7.2 out of 10, Good, (13)
"Very clean Spacious Beds were comfy "
The price is NZ$434
includes taxes & fees
14 July - 15 July
Beautiful, Rehabbed Unit in Shaw Community 4228a

Stylish City Reno Retreat!

8.0 out of 10, Very good, (4)
"The location was great for the zoo and the activities we had planned. The property was very spacious and well cleaned. Would definitely stay again!"
Stylish City Reno Retreat!

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

9.4 out of 10, Exceptional, (6)
The price is NZ$543
includes taxes & fees
14 July - 15 July
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

Cozy 2BR | Near Downtown | St. Louis

8.0 out of 10, Very good, (3)
"This was the absolute perfect little historic place! The beds were ultra comfortable. It was short ride to everything we wanted to do. My kids and I enjoyed our entire stay. "
The price is NZ$381
includes taxes & fees
16 July - 17 July
Cozy 2BR | Near Downtown | St. Louis

Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly

9.6 out of 10, Exceptional, (69)
"We had a great stay "
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly

Amazing Soulard STL Unit, 713a

2.0 star property
8.2 out of 10, Very good, (22)
"Property was clean and had everything we needed for our stay. Close to dining options and farmers market!"
The price is NZ$498
includes taxes & fees
17 July - 18 July
Amazing Soulard STL Unit, 713a

ADayInParis! "FREE" GatedParking&Breakfast!

7.4 out of 10, Good, (13)
"The building was horrible but the apartment itself was amazing parking was a joke the bar across the street was fabulous and the owners of the bar was super helpful and extremely nice (Wave Taco) not a good neighborhood though "
The price is NZ$438
includes taxes & fees
14 July - 15 July
ADayInParis! "FREE" GatedParking&Breakfast!

Modern Soulard 4BR-2BR Group Haven Patio & Fun

7.8 out of 10, Good, (8)
"Our group had a great time on Mardi Gras weekend! We were the perfect walking distance from everywhere we needed to go."
The price is NZ$579
includes taxes & fees
6 Aug - 7 Aug
Modern Soulard 4BR-2BR Group Haven Patio & Fun

Spacious 2 BR Balcony Hideaway

8.4 out of 10, Very good, (5)
"Great overall stay highly recommended and the owner will stay in contact please book here "
Spacious 2 BR Balcony Hideaway

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (15)
"Walking distance to several bars and restaurants, the market, and we got front row parking. "
The price is NZ$285
includes taxes & fees
14 July - 15 July
Cozy Soulard Getaway

PREMIER LOCATION: HEART OF THE ITALIAN NBRHD, THE HILL, Dining&Shops Steps Away

10.0 out of 10, Exceptional, (234)
"Very nice place "
PREMIER LOCATION: HEART OF THE ITALIAN NBRHD, THE HILL, Dining&Shops Steps Away
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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Frequently asked questions

Can I find holiday rentals in Winchester?

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

What are some of the best holiday rentals that Winchester has to offer?

Centrally located in the Tower Grove East neighborhood!: This holiday home rental outside of Winchester is equipped with a selection of books, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, an oven and a microwave.

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 Lone Elk Park. In the wider area, you’ll find Museum of Transportation and The Factory.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.