Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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, (7 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is ￥10,715
￥17,233 total
includes taxes & fees
May 18 - May 19
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Dining

Cute town house with fenced backyard

Cute town house with fenced backyard
Barnhart
9.6 out of 10, Exceptional, (18 reviews)
"We stayed here while visiting family nearby. It met our needs. "
United States
Caren L.
The price is ￥20,239
￥44,083 total
includes taxes & fees
May 18 - May 19
Cute town house with fenced backyard
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)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is ￥21,403
￥45,627 total
includes taxes & fees
May 18 - May 19
Convenience 2 Bedroom House to Explore All of St Louis
Fridge, microwave, oven, stovetop

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
9.2 out of 10, Wonderful, (9 reviews)
The price is ￥8,731
￥44,284 total
includes taxes & fees
May 20 - May 21
Settle into Soulard! 6 beds 2 full baths!
2 bedrooms, desk, iron/ironing board, travel crib

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
8.8 out of 10, Excellent, (25 reviews)
"We were given extra time to check in and out. There were so many things available such as games and even snacks. The home was so warm and welcoming. I’d definitely recommend the stay! "
United States
Lakisha B.
The price is ￥18,890
￥37,034 total
includes taxes & fees
May 18 - May 19
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (47 reviews)
"Our host Bonnie was very welcoming and accommodating great location, we enjoyed every minute and are so grateful."
United States
Lisa Ann J.
The price is ￥15,715
￥37,843 total
includes taxes & fees
May 18 - May 19
Top of Geyer apartment
Smart TV, video games

Spacious & Centrally Located Apt (Sleeps 8)

Spacious & Centrally Located Apt (Sleeps 8)
The Gate
9.8 out of 10, Exceptional, (19 reviews)
"The property is beautifully decorated with plenty of room for everyone. The outdoor space is nice, a little noisy outside, but we still were able to enjoy our time outside."
United States
Jennifer L.
The price is ￥13,017
￥32,364 total
includes taxes & fees
May 18 - May 19
Spacious & Centrally Located Apt (Sleeps 8)
Interior

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (62 reviews)
"The host was awesome! Very responsive to requests and texted back quickly."
United States
Rebecca L.
The price is ￥13,969
￥31,415 total
includes taxes & fees
May 25 - May 26
Cozy Soulard 2BR w/ Free Parking
1 bedroom, free WiFi

6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very Good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is ￥11,112
￥22,224 total
includes taxes & fees
May 25 - May 26
6649 1E | Garden Style Studio Near Forest Park
Interior

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (22 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
The price is ￥10,318
￥29,903 total
includes taxes & fees
May 21 - May 22
Elegant Minimalist Gem w/ Private backyard, W/D
Interior

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (35 reviews)
"Great location and communication from host!!"
United States
rachel l.
The price is ￥8,731
￥28,048 total
includes taxes & fees
May 19 - May 20
Starry Night | Steps to Tower Grove Park
Smart TV, offices

Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck
Soulard
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful place. Loved the location. Will stay again"
United States
Christina T.
The price is ￥13,493
￥32,447 total
includes taxes & fees
May 19 - May 20
Classic Soulard 2BD King Master & Private Deck
Iron/ironing board, travel crib, free WiFi, bed sheets

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 ￥17,620
￥34,096 total
includes taxes & fees
Jun 16 - Jun 17
Stylish South City King 1BR Apt
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, (157 reviews)
"Place was incredibly clean and setup was very conducive to a nice stay. We appreciated the opportunity to stay at such a nice place. "
United States
Jerry D.
The price is ￥10,572
￥24,173 total
includes taxes & fees
May 18 - May 19
Centrally located in the Tower Grove East neighborhood!
Interior

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

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a short get away"
United States
andytrower U.
The price is ￥18,493
￥32,259 total
includes taxes & fees
Jun 7 - Jun 8
Adorable small house - quiet & safe - 2 BR 1 Bath
Dining

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, (19 reviews)
"Great location. Long term stay was excellent!"
United States
Shay W.
Charming Tower Grove Flat-Steps to T.G Park+Grand
TV, offices

Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi

Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi
Maplewood
7.8 out of 10, Good, (6 reviews)
"One of the nicer places I’ve stayed at. Parking is weird on the driveway, but street parking is abundant. "
United States
Paul
The price is ￥12,699
￥26,533 total
includes taxes & fees
Jun 2 - Jun 3
Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi
Interior

Almond Blossoms at TG Park | Fenced Backyard+W/D

Almond Blossoms at TG Park | Fenced Backyard+W/D
Tower Grove South
10.0 out of 10, Exceptional, (14 reviews)
"Great little apartment and the location was perfect for us. Really appreciated the nice firm mattress in the bedroom and the water filter in the fridge. We enjoyed our stay and would definitely stay here again if we are back in the area!"
United States
Jennifer V.
Almond Blossoms at TG Park | Fenced Backyard+W/D
Dining

Magnolia at TG Park | Free PK+WD+Pet Friendly

Magnolia at TG Park | Free PK+WD+Pet Friendly
Tower Grove East
7.8 out of 10, Good, (8 reviews)
"Great renter, great place. "
United States
Howard B.
The price is ￥7,937
￥27,121 total
includes taxes & fees
May 19 - May 20
Magnolia at TG Park | Free PK+WD+Pet Friendly
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
Skinker DeBaliviere
9.8 out of 10, Exceptional, (14 reviews)
"Nice property and nice location."
United States
Richard B.
The price is ￥22,224
￥62,007 total
includes taxes & fees
May 18 - May 19
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
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

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

10/10 Excellent
"The staff could not have been friendlier or more helpful. Check-in, dealing with the valet and wait staff, and the check-out process were all incredibly easy. The room was clean and neat, and offered an incredible view of the Gateway Arch, the Mississippi, and the park. The food options were great, and the daily breakfast buffet had just about everything you could have asked for. One word of caution for light sleepers, there is an interstate that runs just east of the hotel between it and the park. If you are getting a room with an Arch view be aware that you are going to get road noise from that traffic."
Bruce 3-night trip
Posted 1 hour ago
Hyatt Regency St. Louis at The Arch

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

Centrally located in the Tower Grove East neighborhood!: This vacation 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 Lou Fusz Soccer Complex. In the larger area, you’ll find Bellerive Country Club 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.