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Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
St. Louis
9.2 out of 10, Wonderful, (7 reviews)
"This was absolutely perfect and reasonable pricing I surely will be back "
United States
David G.
The price is AU$140
includes taxes & fees
15 July - 16 July
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

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
9.8 out of 10, Exceptional, (8 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is AU$129
includes taxes & fees
15 July - 16 July
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

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
The price is AU$204
includes taxes & fees
18 June - 19 June
6649 2E | Boutique Hotel Studio in Forest Park

6649 1W | Beautiful Getaway in Central St. Louis

6649 1W | Beautiful Getaway in Central St. Louis
Dogtown
7.4 out of 10, Good, (11 reviews)
"Conveniently located "
United States
Nicole S.
The price is AU$229
includes taxes & fees
29 June - 30 June
6649 1W | Beautiful Getaway in Central St. Louis

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (50 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
The price is AU$339
includes taxes & fees
22 June - 23 June
Top of Geyer apartment

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
9.4 out of 10, Exceptional, (11 reviews)
"Clean, convenient and satisfied our needs for this stay. "
United States
Michael L.
The price is AU$398
includes taxes & fees
29 June - 30 June
Settle into Soulard! 6 beds 2 full baths!

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, (49 reviews)
"Everything was great about this property. Very clean, nice neighborhood, attentive host. Will stay again."
United States
Marvista W.
The price is AU$377
includes taxes & fees
16 July - 17 July
Convenience 2 Bedroom House to Explore All of St Louis

6653 1N | European Style Unit Near Forest Park

6653 1N | European Style Unit Near Forest Park
Dogtown
8.4 out of 10, Very good, (5 reviews)
"Good experience overall.. would recommend "
United States
orlando c.
The price is AU$229
includes taxes & fees
29 June - 30 June
6653 1N | European Style Unit Near Forest Park

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Bevo Mill
8.8 out of 10, Excellent, (28 reviews)
"Well supplied, responsive host, great location! "
United States
Christine C.
The price is AU$334
includes taxes & fees
23 June - 24 June
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (25 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 AU$215
includes taxes & fees
22 June - 23 June
6655 1N | Elegance Near the St. Louis Arch

Soulard King Loft near Anheuser-Busch Brewery

Soulard King Loft near Anheuser-Busch Brewery
Soulard
10.0 out of 10, Exceptional, (3 reviews)
"Great location and comfortable stay!"
United States
Leigh S.
The price is AU$289
includes taxes & fees
21 June - 22 June
Soulard King Loft near Anheuser-Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Soulard
10.0 out of 10, Exceptional, (109 reviews)
"The house just has a good vibe and I love how close it is to the city."
United States
Sammie K.
The price is AU$332
includes taxes & fees
21 June - 22 June
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony
The Gate
8.4 out of 10, Very good, (11 reviews)
"We absolutely ADORE this property! The location can’t be beat, parking is a breeze (you do have to figure out getting to it the first time), amenities are close and everything was clean and well-stocked. It IS on the 3rd floor up narrow stairs, but cute, Cute, CUTE!"
United States
April
The price is AU$268
includes taxes & fees
15 July - 16 July
Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (139 reviews)
"The space was very clean, cozy and quiet. There was plenty of room to be comfortable to both rest and have time to get work done or relax in the living room area. The location was very convenient for everything we were visiting St Louis for! (We could walk to both the Fabulous Fox Theatre and Foundry - about 15 min each, and it was a very short trip to the Enterprise Center)"
United States
Jordan
The price is AU$196
includes taxes & fees
24 June - 25 June
White House at Grand Central

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Beatiful home close to venues and shops. "
United States
Kelly H.
The price is AU$282
includes taxes & fees
13 July - 14 July
Stylish South City King 1BR Apt

Luxury stay with all you need within and around

Luxury stay with all you need within and around
Fox Park
9.2 out of 10, Wonderful, (15 reviews)
"Convenient street parking, convenient location, clean, good communication throughout stay"
United States
Kala K.
The price is AU$286
includes taxes & fees
18 June - 19 June
Luxury stay with all you need within and around

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic place. "
United States
Andrew W.
The price is AU$297
includes taxes & fees
18 June - 19 June
Soulard King 1BR - Personal Gym and Sauna Oasis

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, (158 reviews)
"Place was incredibly clean and setup was very conducive to a nice stay. We appreciated the opportunity to stay at such a nice place. "
United States
Jerry D.
The price is AU$236
includes taxes & fees
24 June - 25 June
Centrally located in the Tower Grove East neighborhood!

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (36 reviews)
"Great location and communication from host!!"
United States
rachel l.
The price is AU$333
includes taxes & fees
23 June - 24 June
Starry Night | Steps to Tower Grove Park

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck
Soulard
10.0 out of 10, Exceptional, (4 reviews)
"Great location to all Soulard has to offer."
United States
Lori H.
The price is AU$328
includes taxes & fees
18 June - 19 June
Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, we have holiday rentals where you'll be just 9.5 mi (15.3 km) from Six Flags St. Louis, providing a more secluded option if you want peace and quiet.

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

Centrally located in the Tower Grove East neighborhood!: This holiday home rental outside of Winchester is equipped with a selection of books, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, an oven and a microwave.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Six Flags St. Louis, or get outside and enjoy nature at Lou Fusz Soccer Complex. In the wider area, you’ll find St. Louis Zoo and Museum of Transportation.

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.