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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

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

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

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
Ballwin
7.8 out of 10, Good, (23 reviews)
"Nice and roomy place! The shower was a little messy when we went but everything else wemt well"
United States
alex h.
$145 nightly
The price is $155
Sep 20 - Sep 21
Total with taxes and fees
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. Charming 3-bedroom house in delightful Ballwin and basement is not included

Charming 3-bedroom house in delightful Ballwin and basement is not included
Ballwin
7.2 out of 10, Good, (7 reviews)
"House is located in quiet neighborhood. As described with 3 bedrooms 1 bath. Had adequate towels and supplies in kitchen. Cleanish, was not sure if sheets had been cleaned. Overall, a decent place to stay."
United States
Stephanie N.
$250 nightly
The price is $267
Aug 31 - Sep 1
Total with taxes and fees
Charming 3-bedroom house in delightful Ballwin and basement is not included
A hotel lobby with a staircase, a reception desk, and a chandelier.

3. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic place!"
United States
Anonymous traveler
$66 nightly
The price is $77
Aug 31 - Sep 1
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
A spacious living area with a dining table, sofa, and a large window with blinds.

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

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
10.0 out of 10, Exceptional, (23 reviews)
"I think the best part was that there were little hidden restaurants well within walking distance. It was an excellent stay, the accommodation were cozy."
United States
christine
$153 nightly
The price is $180
Aug 31 - Sep 1
Total with taxes and fees
Stunning Minimalist Gem | 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.

5. 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
$237 nightly
The price is $256
Sep 1 - Sep 2
Total with taxes and fees
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
A modern kitchen with a dining area, built-in cabinets, and a large window.

6. Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.4 out of 10, Exceptional, (26 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
$153 nightly
The price is $180
Aug 31 - Sep 1
Total with taxes and fees
Elegant Minimalist Gem w/ Private backyard, W/D
A living room with a green sofa, a wooden coffee table, and hanging plants.

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

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.2 out of 10, Good, (14 reviews)
"Great place. Clean and spacious"
United States
Isai
$187 nightly
The price is $187
Sep 3 - Sep 4
Total with taxes and fees
Safe and private apt-Near Forest Park-Free parking
A bedroom with a large bed, a bedside table, a chair, a desk, a mirror, and a door.

8. 6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very Good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
$142 nightly
The price is $142
Aug 31 - Sep 1
Total with taxes and fees
6649 2E | Boutique Hotel Studio in Forest Park
A living room with a sofa, a coffee table, a TV, and a ceiling fan.

9. Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (40 reviews)
"Clean, great location and thanks for quick responses"
United States
Martha E M.
$158 nightly
The price is $185
Aug 31 - Sep 1
Total with taxes and fees
Starry Night | Steps to Tower Grove Park
A spacious living room with hardwood flooring, a ceiling fan, a wooden dining table with benches, a sofa, and a coffee table.

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

Almond Blossoms at TG Park | Fenced Backyard+W/D
Tower Grove South
9.8 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay and loved how close to park it was located."
United States
Pam Y.
$158 nightly
The price is $185
Aug 31 - Sep 1
Total with taxes and fees
Almond Blossoms at TG Park | Fenced Backyard+W/D
A bedroom with a bed, a dresser, and a nightstand. There is a hallway leading to a bathroom and a kitchen.

11. 6647 1W | Quaint Studio in Central St. Louis

6647 1W | Quaint Studio in Central St. Louis
Dogtown
8.2 out of 10, Very Good, (28 reviews)
"Great location, secure parking, overall great stay "
United States
Marcus
$140 nightly
The price is $140
Aug 31 - Sep 1
Total with taxes and fees
6647 1W | Quaint Studio in Central St. Louis
A kitchen with a view to a patio, a refrigerator, and a trash can.

12. Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay! Beautiful property! "
United States
Carrie G.
$248 nightly
The price is $276
Aug 31 - Sep 1
Total with taxes and fees
Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters
A spacious living area with a dining table, chairs, a sofa, and a ceiling fan.

13. Irises at TG Park | Fenced Backyard+W/D+Storage

Irises at TG Park | Fenced Backyard+W/D+Storage
Tower Grove South
9.2 out of 10, Wonderful, (17 reviews)
"The apartment was just what we needed Perfect for a weekend getaway "
United States
Robert W.
$152 nightly
The price is $179
Sep 21 - Sep 22
Total with taxes and fees
Irises at TG Park | Fenced Backyard+W/D+Storage
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

14. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (41 reviews)
"Great spot!"
United States
Anonymous traveler
$66 nightly
The price is $77
Aug 31 - Sep 1
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
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.

15. 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, (170 reviews)
"Great place!"
United States
Arthur S.
$142 nightly
The price is $153
Aug 31 - Sep 1
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a refrigerator. There is a dining table with chairs and a ceiling fan.

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

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (196 reviews)
"Looks exactly like the pictures. Clean, beautiful shower. Friendly staff, had no problems answering questions, had all the things you needed to relax for a few days with a couple of friends. The neighborhood is lovely & peaceful at night. Beautiful yard. So pleased I came across this cottage. Thanks guy, our stay was awesome"
United States
Crystal
$141 nightly
The price is $152
Aug 31 - Sep 1
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

17. 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, (50 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
$246 nightly
The price is $266
Sep 27 - Sep 28
Total with taxes and fees
Convenience 2 Bedroom House to Explore All of St Louis
A room with a dining table and chairs, a white door with glass panels, and hardwood flooring.

18. 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, (21 reviews)
"Great location, responsive host & perfect for our short stay! "
United States
Bekah K.
$149 nightly
The price is $174
Aug 31 - Sep 1
Total with taxes and fees
Charming Tower Grove Flat-Steps to T.G Park+Grand
A bedroom with a bed, bedside table, and a large painting on the wall.

19. 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
Sep 7 - Sep 8
Total with taxes and fees
6649 1E | Garden Style Studio Near Forest Park

20. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (30 reviews)
"Great place to stay for the weekend. Cute and clean. Nice area with lot's of places in walking distance. I will definitely stay again."
United States
Brigitte B.
$150 nightly
The price is $150
Aug 31 - Sep 1
Total with taxes and fees
6655 1N | Elegance Near the St. Louis 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

Live by Loews - St.Louis

Live by Loews - St.Louis

10/10 Excellent
"First time staying at this brand. Loved this stay. In town for couple Cardinals games. Great walkable location, part of Ballpark Village, is right across street from ballpark. Super staff. Awesome indoor/outdoor bar/restaurant/lounge, plus a rooftop bar/lounge. Do have happy hr with reasonable drink prices. Hotel is newer, trendy vibe & decor. Hotel is quiet, heard no one in halls or room doors….don’t get the people who walk out their room and let door slam shut behind em. Doors are slow close which is nice. Bathrooms could use more hooks and maybe couple small shelves. Luggage carts are kept locked, need to ask for one. Def stay here again."
Jessica 1-night trip
Posted less than an hour ago
Live by Loews - St.Louis

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 $77 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?

4BR 2BA Modern Family Home with Private Heated Inground Pool Open March 1-Nov11: This vacation home rental outside of Winchester offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Kirkwood 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.