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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
8.0 out of 10, Very good, (25 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
$130 nightly
The price is $139
Nov 9 - Nov 10
Total with taxes and fees
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Property grounds

2. 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.
$104 nightly
The price is $110
Nov 7 - Nov 8
Total with taxes and fees
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
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.

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

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (21 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
$161 nightly
The price is $191
Nov 9 - Nov 10
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.

4. 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
8.8 out of 10, Excellent, (74 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
$238 nightly
The price is $258
Nov 16 - Nov 17
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 fireplace, a dining table, and a sofa.

5. Historic STL Home near Clayton/Massive Backyard

Historic STL Home near Clayton/Massive Backyard
University City
$271 nightly
The price is $314
Nov 8 - Nov 9
Total with taxes and fees
Historic STL Home near Clayton/Massive Backyard
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

6. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.4 out of 10, Exceptional, (43 reviews)
"Great spot!"
United States
Anonymous traveler
$55 nightly
The price is $64
Nov 11 - Nov 12
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A spacious foyer with a grand staircase, a piano, and a large rug.

7. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.2 out of 10, Very good, (168 reviews)
"Very spacious clean old house apartments"
United States
Priscilla
$134 nightly
The price is $151
Nov 8 - Nov 9
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.

8. 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, (55 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
$234 nightly
The price is $254
Nov 29 - Nov 30
Total with taxes and fees
Convenience 2 Bedroom House to Explore All of St Louis
A residential building with a patio area featuring outdoor furniture and string lights.

9. 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, (21 reviews)
"What a great place to stay! Clean, well stocked, and very spacious. Would definitely book again."
United States
Lynn D.
$248 nightly
The price is $278
Nov 16 - Nov 17
Total with taxes and fees
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
Living area

10. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (34 reviews)
"I loved the security aspect of this rental. Felt very safe and it is very close to Forest park which is amazing"
United States
heather d.
$142 nightly
The price is $142
Nov 9 - Nov 10
Total with taxes and fees
6655 1N | Elegance Near the St. Louis Arch
A bathroom with a floral shower curtain, a white sink, a mirror, and a bicycle-themed picture on the wall.

11. 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.
$142 nightly
The price is $142
Nov 9 - Nov 10
Total with taxes and fees
6653 2S | Jewel of Central St. Louis
A living room with a sofa, armchair, coffee table, and a TV.

12. 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
$152 nightly
The price is $152
Nov 9 - Nov 10
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.

13. 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.
$272 nightly
The price is $297
Nov 17 - Nov 18
Total with taxes and fees
Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.
A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

14. Casa de Saint Charles

Casa de Saint Charles
Saint Charles
9.2 out of 10, Wonderful, (22 reviews)
"Everything was very nice and beautiful and perfectly set up for us will book again"
United States
Xavier H.
$298 nightly
The price is $314
Nov 9 - Nov 10
Total with taxes and fees
Casa de Saint Charles
A modern living room with a dark wood floor, a leather sofa, and a fluffy rug.

15. 3BR Dogtown Bungalow |Office + Bar

3BR Dogtown Bungalow |Office + Bar
Dogtown
9.4 out of 10, Exceptional, (41 reviews)
"We loved our stay! The location was fantastic and perfect for our family of five."
United States
Laura F.
$301 nightly
The price is $344
Nov 23 - Nov 24
Total with taxes and fees
3BR Dogtown Bungalow |Office + Bar
A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

16. Home Near Main with Pet-Friendly Yard and Office

Home Near Main with Pet-Friendly Yard and Office
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
$236 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
Home Near Main with Pet-Friendly Yard and Office
An outdoor hot tub area with seating and a covered patio.

17. Private Basement - Two King Beds and Hot Tub

Private Basement - Two King Beds and Hot Tub
Saint Charles
9.6 out of 10, Exceptional, (5 reviews)
"Clean. The patio was very comfortable and nice to sit and relax. The beds were also very comfortable."
United States
Beth S.
$291 nightly
The price is $327
Nov 8 - Nov 9
Total with taxes and fees
Private Basement - Two King Beds and Hot Tub
A two-story house with a covered porch, stone exterior, and a large tree in the foreground.

18. Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (50 reviews)
"Unit was very clean and comfortable. Lots of space inside and outside for yard and parking. Host was responsive to our questions. Local restaurants with good food and service were nearby."
United States
John D.
$156 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
Pet and kid friendly duplex with 2 bedrooms
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.

19. 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, (181 reviews)
"Great place!"
United States
Arthur S.
$134 nightly
The price is $145
Nov 9 - Nov 10
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!
Free breakfast available on-site.

20. Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Westport
9.8 out of 10, Exceptional, (6 reviews)
"Everything from the staff to the amenities to the rooms were amazing! Definitely recommend staying here! "
Canada
Lashon C.
$242 nightly
The price is $280
Nov 29 - Nov 30
Total with taxes and fees
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
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

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

10/10 Excellent
"Use the pool at dinner time when children are not around... otherwise, do not use the pool. Breakfast was very good. Staff was friendly and helpful!!!"
Amy 1-night trip
Posted 13 hours ago
Hampton Inn St. Louis-Downtown (At the Gateway Arch)

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 $64 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.