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Winchester Holiday Rentals

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Check prices for these dates

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

Our top choices for Winchester holiday 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.
The price is HK$530
HK$1,155 total
includes taxes & fees
19 Oct - 20 Oct
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
The price is HK$424
HK$1,409 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is HK$628
HK$1,177 total
includes taxes & fees
27 Oct - 28 Oct
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 traveller
The price is HK$459
HK$532 total
includes taxes & fees
1 Nov - 2 Nov
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
The price is HK$392
HK$1,334 total
includes taxes & fees
18 Oct - 19 Oct
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
The price is HK$452
HK$1,443 total
includes taxes & fees
21 Oct - 22 Oct
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
The price is HK$981
HK$1,934 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is HK$672
HK$2,199 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$628
HK$1,177 total
includes taxes & fees
27 Oct - 28 Oct
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.
The price is HK$628
HK$1,256 total
includes taxes & fees
29 Oct - 30 Oct
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.
The price is HK$593
HK$920 total
includes taxes & fees
19 Oct - 20 Oct
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
The price is HK$597
HK$973 total
includes taxes & fees
27 Oct - 28 Oct
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.
The price is HK$926
HK$2,064 total
includes taxes & fees
27 Oct - 28 Oct
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.
The price is HK$549
HK$1,099 total
includes taxes & fees
2 Nov - 3 Nov
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.
The price is HK$628
HK$1,177 total
includes taxes & fees
29 Oct - 30 Oct
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
The price is HK$667
HK$1,256 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is HK$1,177
HK$2,438 total
includes taxes & fees
26 Oct - 27 Oct
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.
The price is HK$1,138
HK$3,206 total
includes taxes & fees
4 Nov - 5 Nov
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.
The price is HK$388
HK$1,367 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is HK$628
HK$1,310 total
includes taxes & fees
29 Oct - 30 Oct
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 10 hours ago
Drury Plaza Hotel St. Louis Union Station

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:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, we have holiday rentals where you'll be just 13.2 mi (21.2 km) from St. Louis Zoo, providing a more secluded option if you want peace and quiet.

What are some of the best holiday rentals that Winchester has to offer?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Winchester is located in the city centre, and has a patio, a garden and a BBQ 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 holiday with amenities such as 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 wider area, you’ll find The Factory and Magic House - St. Louis Children's Museum.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.