Winchester Holiday Rentals

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Holiday Rentals in Winchester

Kasa Forest Park St. Louis

4.0 star property
9.0 out of 10, Wonderful, (112)
"Super clean and convenient for the price. Would put it against rooms costing a lot more"
Kasa Forest Park St. Louis

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (94)
"Nice place only thing I wish the housekeepers start mopping the floors "
The price is AU$288
includes taxes & fees
1 Dec - 2 Dec
White House at Grand Central

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (192)
"Host and house were both great. "
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

The St. Charles Guest House, lovely historic home, fun for families and groups

10.0 out of 10, Exceptional, (119)
"We loved this place and the location! We plan on returning one day!"
The St. Charles Guest House, lovely historic home, fun for families and groups

Funky mini loft in fox park! Pet friendly!!

7.4 out of 10, Good, (34)
"I really like how the loft is decorated and we slept great. The owner was very quick to respond to any questions I had. "
The price is AU$243
includes taxes & fees
29 Nov - 30 Nov
Funky mini loft in fox park! Pet friendly!!

Craigshire Suites

3.0 star property
7.0 out of 10, Good, (1110)
"Great customer service "
The price is AU$269
includes taxes & fees
24 Nov - 25 Nov
Craigshire Suites

The Lofts of North Main Street

9.6 out of 10, Exceptional, (112)
"Loved the vibe, location couldn’t have been better. The unit was clean and had everything we needed. "
The price is AU$411
includes taxes & fees
4 Dec - 5 Dec
The Lofts of North Main Street

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

9.8 out of 10, Exceptional, (58)
"We were extremely impressed with this property and its central location. We were within 10 minutes of the places we visited: the Botanical Gardens, the Arch, and the Budweiser plant tour. We had one question during our stay and the homeowner answered our message to him within minutes. We highly recommend this property and homeowner!"
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly

Entire Dogtown House near Zoo, Forest Park and Wash U

10.0 out of 10, Exceptional, (194)
"Was in STL for a college soccer game. Great location, safe neighborhood, house is very clean, we enjoyed our stay and hope to visit STL for a longer stay. "
The price is AU$320
includes taxes & fees
1 Dec - 2 Dec
Entire Dogtown House near Zoo, Forest Park and Wash U

Boho Bungalow with Great Location!

9.8 out of 10, Exceptional, (39)
"Cute bungalow in a quiet neighborhood. Had the basics. Liked the outdoor area with pretty sunset. "
Boho Bungalow with Great Location!

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

9.8 out of 10, Exceptional, (120)
"This is a great location to enjoy all the amenities on The Hill, without having to drive. Parking can be a little issue, but doable. Host was easy to communicate with and provided information as needed."
The price is AU$229
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

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

10.0 out of 10, Exceptional, (242)
"We had a nice night in the comfortable property."
The price is AU$239
includes taxes & fees
4 Dec - 5 Dec
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

St Louis Townhome-Perfect for Groups!

8.0 out of 10, Very good, (33)
"This unit was 1.5 miles away from my granddaughters wedding venue. What a time saver for me and family with the rehearsals and wedding activities. Parking was not an issue as my group had three cars. Easy peasy! Host Dan was very helpful with my check in questions and responded promptly. Sheets were clean, water hot, and truly a wonderful experience for my family. Thanks Dan!"
The price is AU$350
includes taxes & fees
24 Nov - 25 Nov
St Louis Townhome-Perfect for Groups!

Kasa Central West End St. Louis

4.0 star property
8.8 out of 10, Excellent, (47)
"Great property, enjoyed our stay. "
Kasa Central West End St. Louis

Cozy Soulard 2BR w/ Free Parking

9.6 out of 10, Exceptional, (34)
"Thank you Joe for such a wonder stay!!!"
The price is AU$266
includes taxes & fees
8 Dec - 9 Dec
Cozy Soulard 2BR w/ Free Parking

South City Historic Home w/ private carport

9.6 out of 10, Exceptional, (33)
"very clean, really big, "
The price is AU$531
includes taxes & fees
4 Dec - 5 Dec
South City Historic Home w/ private carport

Stylish FoxPark 3BR, King Master

10.0 out of 10, Exceptional, (42)
"Week long stay, no complaints. Comfy beds, well stocked, clean, responsive host. Agree on rough stairs access but the city in general is not well maintained so watch for the potholes outside. "
The price is AU$285
includes taxes & fees
8 Dec - 9 Dec
Stylish FoxPark 3BR, King Master

Remodeled Kirkwood Guest house

10.0 out of 10, Exceptional, (67)
"Nice family neighborhood, very quiet, rental is immaculate clean and looks new. We will be back. "
Remodeled Kirkwood Guest house

Blue Door Bungalow | JZ Vacation Rentals

9.6 out of 10, Exceptional, (28)
"We picked this place to meet up with my 20-something son from DC and their 80-something grandparents (my parents) from the Springfield area. The layout was exceptional-only 4 steps to get in, and my parents could go to their bedroom, kitchen and living area on the same level, while the boys could hang out downstairs watching TV or playing Air Hockey. It worked perfectly for us for the weekend."
Blue Door Bungalow | JZ Vacation Rentals

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

10.0 out of 10, Exceptional, (205)
"The apartment was so clean and cozy. It made us feel so comfortable. Great location on The Hill. "
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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Other types of properties in Winchester you may be interested in

Hollywood Casino & Hotel St. Louis

3.5 star property
8.4 out of 10, Very good, (1694)
"It would help if you could have scooters for those have walkers. The parking lot to the room was still far. I opt out having to go to the Casino with my husband because of the distance for me to walk from my room to the gambling area."
The price is AU$195
includes taxes & fees
1 Dec - 2 Dec
Hollywood Casino & Hotel St. Louis

Hyatt Regency St. Louis at The Arch

4.0 star property
8.4 out of 10, Very good, (3507)
"Paying 42 dollars for parking is outrageous "
The price is AU$150
includes taxes & fees
1 Dec - 2 Dec
Hyatt Regency St. Louis at The Arch

Clayton Plaza Hotel & Extended Stay

3.5 star property
9.0 out of 10, Wonderful, (2928)
"Safe area. Great breakfast buffet "
The price is AU$187
includes taxes & fees
8 Dec - 9 Dec
Clayton Plaza Hotel & Extended Stay
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Funky mini loft in fox park! Pet friendly!!: This holiday home rental outside of Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Route 66 State Park. In the wider area, you’ll find The Factory and Chesterfield Sports Fusion.

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.