Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

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, (7 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is €91
includes taxes & fees
6 Jul - 7 Jul
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 €126
includes taxes & fees
8 Jun - 9 Jun
6649 2E | Boutique Hotel Studio in Forest Park

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (24 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 €133
includes taxes & fees
8 Jun - 9 Jun
6655 1N | Elegance Near the St. Louis Arch

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (22 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
The price is €161
includes taxes & fees
8 Jun - 9 Jun
Elegant Minimalist Gem w/ Private backyard, W/D

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, (26 reviews)
"Just was amazing!! I felt completely at home! Comfortable and able to relax and really let my hair down! Will definitely be staying here again!! "
United States
Heather G.
The price is €200
includes taxes & fees
9 Jun - 10 Jun
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Walk to Bars & Dining: Historic Benton Park Gem

Walk to Bars & Dining: Historic Benton Park Gem
3.0 star property
Benton Park
The price is €240
includes taxes & fees
17 Jun - 18 Jun
Walk to Bars & Dining: Historic Benton Park Gem

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)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is €255
includes taxes & fees
8 Jun - 9 Jun
Convenience 2 Bedroom House to Explore All of St Louis

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (64 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
The price is €180
includes taxes & fees
8 Jun - 9 Jun
Cozy Soulard 2BR w/ Free Parking

Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a short get away"
United States
andytrower U.
The price is €169
includes taxes & fees
1 Jul - 2 Jul
Adorable small house - quiet & safe - 2 BR 1 Bath

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 €142
includes taxes & fees
8 Jun - 9 Jun
6649 1W | Beautiful Getaway in Central St. Louis

6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is €125
includes taxes & fees
16 Jun - 17 Jun
6649 1E | Garden Style Studio Near Forest Park

Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (73 reviews)
"Kitchen was fully equipped had a great time"
United States
Kevin M.
The price is €202
includes taxes & fees
8 Jun - 9 Jun
Classy Midtown 2BR, King Master

Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.8 out of 10, Good, (11 reviews)
"We enjoyed our stay"
United States
Dee
The price is €158
includes taxes & fees
9 Jun - 10 Jun
Safe and private apt-Near Forest Park-Free parking

Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
10.0 out of 10, Exceptional, (19 reviews)
"Good host and amenities."
United States
Adam N.
The price is €177
includes taxes & fees
7 Jun - 8 Jun
Stunning Minimalist Gem | Fenced Backyard + W/D

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (48 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
The price is €207
includes taxes & fees
8 Jun - 9 Jun
Top of Geyer apartment

Cute town house with fenced backyard

Cute town house with fenced backyard
Barnhart
9.6 out of 10, Exceptional, (18 reviews)
"We stayed here while visiting family nearby. It met our needs. "
United States
Caren L.
The price is €242
includes taxes & fees
9 Jun - 10 Jun
Cute town house with fenced backyard

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
Skinker DeBaliviere
9.8 out of 10, Exceptional, (15 reviews)
"Nice property and nice location."
United States
Richard B.
The price is €288
includes taxes & fees
8 Jun - 9 Jun
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

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, (157 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 €135
includes taxes & fees
9 Jun - 10 Jun
Centrally located in the Tower Grove East neighborhood!

Romantic Augusta Cottage w/ hot tub

Romantic Augusta Cottage w/ hot tub
Augusta
9.8 out of 10, Exceptional, (41 reviews)
"Great little place. Nice and relaxing!"
United States
Chris R.
The price is €272
includes taxes & fees
11 Jun - 12 Jun
Romantic Augusta Cottage w/ hot tub

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 €142
includes taxes & fees
6 Jul - 7 Jul
6653 1N | European Style Unit Near Forest Park
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, apart-hotels, 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 favorite 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 depends 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 €116 per night. Entering your travel dates in the search wizard you might find 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.