Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

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
9.6 out of 10, Exceptional, (5 reviews)
"We had a nice stay in the area, and we were looking for a reasonably priced lodging for the whole family. There are a couple inflatable mattresses included in case additional beds are required. The full kitchen was appreciated, as was the comfortable couch. Solid proximity to other businesses and towns. The property is a little tricky to spot from afar off the side of the road, but it's easy to see once you're near it (Google maps is helpful). Overall, a good stay & I would stay here again!"
United States
Zach L.
The price is ￥8,607
￥14,997 total
includes taxes & fees
Mar 30 - Mar 31
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Dining

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

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.4 out of 10, Exceptional, (14 reviews)
"A great apartment in a great area, close to Tower Grove park and lots of St. Louis activities! I live in the St. Louis area and had an extended stay here through my house renovations. Highly recommended for both short and longer stays!"
United States
Leah S.
The price is ￥8,129
￥27,418 total
includes taxes & fees
Mar 30 - Mar 31
Charming Tower Grove Flat-Steps to T.G Park+Grand
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 ￥11,656
￥31,573 total
includes taxes & fees
Mar 30 - Mar 31
Magnolia at TG Park | Free PK+WD+Pet Friendly
Interior

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (30 reviews)
"The apartment was very clean and comfortable with a great location."
United States
Paul C.
The price is ￥7,810
￥27,044 total
includes taxes & fees
Apr 14 - Apr 15
Starry Night | Steps to Tower Grove Park
1 bedroom, free WiFi

Garden style studio @ Forest Park & City!

Garden style studio @ Forest Park & City!
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 ￥11,157
￥22,314 total
includes taxes & fees
Mar 29 - Mar 30
Garden style studio @ Forest Park & City!
1 bedroom, free WiFi

Forest Park Style Studio in STL!

Forest Park Style Studio in STL!
Dogtown
8.0 out of 10, Very Good, (14 reviews)
"Loved staying here. The room was clean and cozy. Loved the old world charm of the property. "
United States
Sarah
The price is ￥11,157
￥22,633 total
includes taxes & fees
Apr 12 - Apr 13
Forest Park Style Studio in STL!
Interior

Pet-Friendly 1BR Apartment

Pet-Friendly 1BR Apartment
Mount Pleasant
9.0 out of 10, Wonderful, (14 reviews)
"The kitchen was well stocked, great bathroom towels and pillows. Close to a park for dog walks. "
United States
Dedra
The price is ￥14,441
￥30,221 total
includes taxes & fees
Apr 7 - Apr 8
Pet-Friendly 1BR Apartment
Interior

Stunning Townhome 920 in The Grove

Stunning Townhome 920 in The Grove
The Grove
9.4 out of 10, Exceptional, (22 reviews)
"We arrived at the townhouse and the bed sheets on every bed were stained and had hair on them. The floors had garbage on the floor. The bathroom curtains had mold and the toilets were dirty. We didn’t take towels since it was listed on there but the ones they had were dirty we had to go buy some. One of the bed was broken and the freezer didn’t work either I communicated all of this to the host and received to no respond. "
United States
Jennifer
The price is ￥9,404
￥37,616 total
includes taxes & fees
Apr 1 - Apr 2
Stunning Townhome 920 in The Grove
Interior

Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.8 out of 10, Exceptional, (11 reviews)
"Clean, very comfortable apartment in a great location: easy walk to restaurants, coffee shops, Francis Park. Attractive, quiet, tree-lined neighborhood. Would definitely stay here again!"
United States
Jack S.
The price is ￥10,998
￥30,772 total
includes taxes & fees
Apr 1 - Apr 2
Chic Minimalist Gem w/ Fenced Backyard + W/D
Fridge, microwave, oven, stovetop

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥8,766
￥44,943 total
includes taxes & fees
Mar 31 - Apr 1
Settle into Soulard! 6 beds 2 full baths!
1 bedroom, iron/ironing board, free WiFi

Quaint Studio in STL Central!

Quaint Studio in STL Central!
Dogtown
8.2 out of 10, Very Good, (24 reviews)
"Quaint apartment with all the amenities you would need for a weekend trip."
United States
Tirzah W.
The price is ￥11,157
￥22,314 total
includes taxes & fees
Mar 29 - Mar 30
Quaint Studio in STL Central!
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, (146 reviews)
"We enjoyed our stay! Very nice!!"
United States
Pam L.
The price is ￥10,759
￥24,428 total
includes taxes & fees
Apr 1 - Apr 2
Centrally located in the Tower Grove East neighborhood!
TV, offices

Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)

Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
Mount Pleasant
7.8 out of 10, Good, (13 reviews)
"Nice, quiet apartment in a South City four-family. Everything we needed was there and it was very tidy and clean. We enjoyed our stay! "
United States
Stefene R.
The price is ￥15,262
￥31,276 total
includes taxes & fees
Apr 2 - Apr 3
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
Smart TV, video games

Spacious & Centrally Located Apt (Sleeps 8)

Spacious & Centrally Located Apt (Sleeps 8)
The Gate
9.8 out of 10, Exceptional, (18 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 ￥13,229
￥32,206 total
includes taxes & fees
Apr 13 - Apr 14
Spacious & Centrally Located Apt (Sleeps 8)
TV

Comfy Walk to Forest Park!

Comfy Walk to Forest Park!
Dogtown
8.4 out of 10, Very Good, (5 reviews)
"Good experience overall.. would recommend "
United States
orlando c.
The price is ￥12,751
￥25,502 total
includes taxes & fees
Mar 29 - Mar 30
Comfy Walk to Forest Park!
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (46 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 ￥15,780
￥36,883 total
includes taxes & fees
Apr 7 - Apr 8
Top of Geyer apartment
Dining

Serenity Log Inn -Log out and Log Inn to Serenity

Serenity Log Inn -Log out and Log Inn to Serenity
Imperial
10.0 out of 10, Exceptional, (38 reviews)
"Everything exceeded our expectations, host was very accommodating, would definitely stay again."
United States
dennis m.
The price is ￥14,345
￥29,712 total
includes taxes & fees
Mar 31 - Apr 1
Serenity Log Inn -Log out and Log Inn to Serenity
TV

Central Jewel of Saint Louis!

Central Jewel of Saint Louis!
Dogtown
8.0 out of 10, Very Good, (24 reviews)
"It was clean and one of the best vrbo stays I went to."
United States
Sabria S.
Central Jewel of Saint Louis!
Smart TV, fireplace

Cozy Soulard Getaway

Cozy Soulard Getaway
Soulard
9.2 out of 10, Wonderful, (42 reviews)
"The host was accommodating and the amenities is expected. The location was centrally located for us and the area is quiet. Would love to stay on my next visit "
United States
CLARISSA W.
The price is ￥15,461
￥40,804 total
includes taxes & fees
Mar 30 - Mar 31
Cozy Soulard Getaway
TV

Elegance in the STL Arch!

Elegance in the STL Arch!
Dogtown
7.6 out of 10, Good, (21 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is ￥12,751
￥23,908 total
includes taxes & fees
Mar 29 - Mar 30
Elegance in the STL Arch!
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

The Wildwood Hotel

The Wildwood Hotel

10/10 Excellent
"Very friendly staff, clean spacious room, comfortable bed, and quiet. The only thing that could have been better was the breakfast."
Susan K. 2-night trip
Posted 1 hour ago
The Wildwood Hotel

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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This vacation home rental outside of Winchester is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 The Factory and Magic House - St. Louis Children's Museum.

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.