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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester vacation rentals

A set of stone steps leading to a garage with a car parked inside.

1. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Ballwin
7.8 out of 10, Good, (24 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
$138 nightly
The price is $147
Oct 19 - Oct 20
Total with taxes and fees
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A spacious living area with a dining table, sofa, and a large window with blinds.

2. Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
9.8 out of 10, Exceptional, (29 reviews)
"Nice area, very well kept house and easy check-in process. Good parking"
United States
Christopher
$153 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
Stunning Minimalist Gem | Fenced Backyard + W/D
A living room with a sofa, a red armchair, a glass coffee table, and a patterned rug.

3. 6653 1S | Beautiful Unit Near Forest Park

6653 1S | Beautiful Unit Near Forest Park
Dogtown
6.8 out of 10, (10 reviews)
"Fantastic place lots to do, free zoo"
United States
Andrew T.
$150 nightly
The price is $150
Oct 19 - Oct 20
Total with taxes and fees
6653 1S | Beautiful Unit Near Forest Park
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

4. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (42 reviews)
"Great spot!"
United States
Anonymous traveler
$61 nightly
The price is $70
Oct 22 - Oct 23
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A living room with a green sofa, a wooden coffee table, and hanging plants.

5. Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.4 out of 10, Good, (16 reviews)
"I loved that it was in an older building and there is history there. The best were comfortable, and the apartment was spotless."
United States
Machelle
$169 nightly
The price is $169
Oct 19 - Oct 20
Total with taxes and fees
Safe and private apt-Near Forest Park-Free parking
A modern kitchen with a built-in refrigerator, a dining area with a wooden table and benches, a gray sofa, and large windows providing natural light.

6. Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (20 reviews)
"Very nice, clean, modern apartment in a safe, quiet, suburban neighborhood. We were very happy with our stay there for our visit to WashU and St. Louis."
United States
Dave
$157 nightly
The price is $184
Oct 21 - Oct 22
Total with taxes and fees
Chic Minimalist Gem w/ Fenced Backyard + W/D
A living room with a dark hardwood floor, a leather sofa, a ceiling fan, and a flat-screen TV mounted on the wall.

7. Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
Eureka
9.0 out of 10, Wonderful, (72 reviews)
"This was an extraordinary experience with great property and location and the description of the property was exact on. The host was very helpful when it came to anything we was needing very much appreciated and look forward to staying with this property owner again."
United States
Keith
$228 nightly
The price is $246
Oct 20 - Oct 21
Total with taxes and fees
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

8. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (20 reviews)
"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"
United States
Chris B.
$252 nightly
The price is $280
Oct 18 - Oct 19
Total with taxes and fees
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
Living area

9. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (33 reviews)
"Clean and Comfortable."
United States
Toni F.
$150 nightly
The price is $150
Oct 19 - Oct 20
Total with taxes and fees
6655 1N | Elegance Near the St. Louis Arch
A living room with a beige sofa, a dark grey sofa, a glass coffee table, and a red and brown patterned rug.

10. 6653 1N | European Style Unit Near Forest Park

6653 1N | European Style Unit Near Forest Park
Dogtown
8.4 out of 10, Very good, (6 reviews)
"Good experience overall.. would recommend "
United States
orlando c.
$160 nightly
The price is $160
Oct 19 - Oct 20
Total with taxes and fees
6653 1N | European Style Unit Near Forest Park
Property grounds

11. Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 2-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.
$111 nightly
The price is $117
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
A spacious foyer with a grand staircase, a piano, and a large rug.

12. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.2 out of 10, Very good, (165 reviews)
"Nice find in the city"
United States
Mark
$134 nightly
The price is $151
Oct 25 - Oct 26
Total with taxes and fees
White House at Grand Central
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

13. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (53 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
$240 nightly
The price is $260
Oct 21 - Oct 22
Total with taxes and fees
Convenience 2 Bedroom House to Explore All of St Louis
A bedroom with a bed, bedside table, and a large painting on the wall.

14. 6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (25 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
$140 nightly
The price is $140
Nov 2 - Nov 3
Total with taxes and fees
6649 1E | Garden Style Studio Near Forest Park
A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

15. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"Hot water was an issue. Other than that great place to stay"
United States
Ashley C.
$150 nightly
The price is $150
Oct 19 - Oct 20
Total with taxes and fees
6653 2S | Jewel of Central St. Louis
A living room with a sofa, armchair, coffee table, and a TV.

16. 6649 1W | Beautiful Getaway in Central St. Louis

6649 1W | Beautiful Getaway in Central St. Louis
Dogtown
7.2 out of 10, Good, (12 reviews)
"The apt"
United States
Pantung
$160 nightly
The price is $160
Oct 19 - Oct 20
Total with taxes and fees
6649 1W | Beautiful Getaway in Central St. Louis
A modern kitchen with dark cabinets, a central island, stainless steel appliances, and a hanging light fixture.

17. Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
Byrnes Mill
10.0 out of 10, Exceptional, (25 reviews)
"This was a repeat visit for us and we will always try to use this property - if available - when we come back to town! "
United States
Deborah W.
$286 nightly
The price is $311
Oct 21 - Oct 22
Total with taxes and fees
Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
A modern living room with a dark wood floor, a leather sofa, and a fluffy rug.

18. 3BR Dogtown Bungalow |Office + Bar

3BR Dogtown Bungalow |Office + Bar
Dogtown
9.4 out of 10, Exceptional, (41 reviews)
"Tommy's place is in a great location for a St. Louis visit. We walked to Forest park everyday, and hit up some cute coffee shops and restaurants nearby. His place is also very spacious, clean and has great parking."
United States
Patti H.
$361 nightly
The price is $408
Nov 4 - Nov 5
Total with taxes and fees
3BR Dogtown Bungalow |Office + Bar
An open door leading to a dining area with a table and chairs, a painting on the wall, and a wooden floor.

19. Steps to TG Park+Grand | Free PK+WD+Pet Friendly

Steps to TG Park+Grand | Free PK+WD+Pet Friendly
Tower Grove East
9.2 out of 10, Wonderful, (26 reviews)
"Great Stay"
United States
Roger C.
$149 nightly
The price is $174
Oct 20 - Oct 21
Total with taxes and fees
Steps to TG Park+Grand | Free PK+WD+Pet Friendly
A dining area with a wooden table, grey upholstered chairs, a bench, a patterned rug, a brick wall, a framed picture, and a potted plant.

20. 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, (179 reviews)
"Great place!"
United States
Arthur S.
$149 nightly
The price is $161
Oct 20 - Oct 21
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!
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

Drury Plaza Hotel St. Louis Union Station

Drury Plaza Hotel St. Louis Union Station

10/10 Excellent
"Great location! The hotel is within walking distance of many places, making it easy to explore the area. The Ferris wheel is right in front of the hotel, which is such a nice touch! Even if you don’t take a ride, just enjoying the beautiful view is worth it. .😊"
Meijing 2-night trip
Posted 11 hours ago
Drury Plaza Hotel St. Louis Union Station

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $70 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Laumeier Sculpture 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.