Winchester Holiday Rentals

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Holiday Rentals in Winchester

Stylish South City King 1BR Apt
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great location, great accommodations, great host."
United States
Scott W.
The price is AU$250
includes taxes & fees
21 Oct - 22 Oct
Stylish South City King 1BR Apt
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
2.0 star property
8.4 out of 10, Very good, (22)
"Excellent location very clean place "
United States
kimberly b.
The price is AU$483
includes taxes & fees
21 Oct - 22 Oct
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
Sunny SparkingClean King bed Apt- CreveCoeurPark
9.8 out of 10, Exceptional, (12)
"Good Stay"
United States
Lanai
The price is AU$359
includes taxes & fees
28 Oct - 29 Oct
Sunny SparkingClean King bed Apt- CreveCoeurPark
Charming 3-bedroom house with WiFi, and fenced-in backyard in serene Byrnes Mill
2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place to stay. Huge fenced in backyard for dogs to run around. Host was real helpful with any questions we had"
United States
Michael A.
The price is AU$464
includes taxes & fees
23 Oct - 24 Oct
Charming 3-bedroom house with WiFi, and fenced-in backyard in serene Byrnes Mill
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
10.0 out of 10, Exceptional, (282)
"Great place, great location"
United States
Dennis R.
The price is AU$248
includes taxes & fees
22 Oct - 23 Oct
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Adorable small house - quiet & safe - 2 BR 1 Bath
9.4 out of 10, Exceptional, (13)
"Great place for a short get away"
United States
andytrower U.
The price is AU$289
includes taxes & fees
26 Oct - 27 Oct
Adorable small house - quiet & safe - 2 BR 1 Bath
White House at Grand Central
4.0 star property
8.4 out of 10, Very good, (121)
"The property is in a Safe neighborhood. "
United States
Alexandria
White House at Grand Central
Smoke Free!!The Rock House Bnb, StL. Centrally Located + Park. 8 person Max!
9.4 out of 10, Exceptional, (10)
"This place was the right fit for a quick trip! Every amenity need!"
United States
Simcha B.
The price is AU$432
includes taxes & fees
21 Oct - 22 Oct
Smoke Free!!The Rock House Bnb, StL. Centrally Located + Park. 8 person Max!
Convenience 2 Bedroom House to Explore All of St Louis
9.8 out of 10, Exceptional, (34)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is AU$409
includes taxes & fees
21 Oct - 22 Oct
Convenience 2 Bedroom House to Explore All of St Louis
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (149)
"Very walkable to everything in The Hill area! "
United States
Anonymous traveller
The price is AU$224
includes taxes & fees
21 Oct - 22 Oct
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Cute ranch house -quiet & safe -3 BR 1 Bath
9.6 out of 10, Exceptional, (20)
"Check in was interesting but owner communicated very well. Overall, it was what we needed for our trip. "
United States
Patrick W.
The price is AU$323
includes taxes & fees
26 Oct - 27 Oct
Cute ranch house -quiet & safe -3 BR 1 Bath
Stylish South City 2BR w/ Garage & Blazing Wi-fi
9.6 out of 10, Exceptional, (48)
"Very clean and comfortable. "
United States
Michael M.
The price is AU$287
includes taxes & fees
21 Oct - 22 Oct
Stylish South City 2BR w/ Garage & Blazing Wi-fi
Cute town house with fenced backyard
9.6 out of 10, Exceptional, (17)
"It was a great place to stay for our needs we had our little dog with us as was there for weekend, it had a nice fenced back yard we could let her just go out didn't have to have her on leash. Was very nice inside clean well kept, beds were surprising comfortable. The host stayed in contact and answered a lot questions before we arrived which put me a ease for our trip. High recommand this place if needing to stay in the area. "
United States
Terry
The price is AU$406
includes taxes & fees
26 Oct - 27 Oct
Cute town house with fenced backyard
Classy Midtown 3BR, King Master
10.0 out of 10, Exceptional, (54)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
The price is AU$288
includes taxes & fees
28 Oct - 29 Oct
Classy Midtown 3BR, King Master
Top of Geyer apartment
9.8 out of 10, Exceptional, (40)
"What a great location!! We enjoyed food at the Great Grizzly that is located downstairs. The staff is amazing and the owner made sure to come and greet us while we were there. We had breakfast at Cafe Miami which is only a 5 minute walk. Everything in the VRBO was as described and very comfortable. We would definitely book again."
United States
Jessica P.
The price is AU$293
includes taxes & fees
22 Oct - 23 Oct
Top of Geyer apartment
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park
2.0 star property
10.0 out of 10, Exceptional, (8)
"My friends and I really enjoyed how close it was to the loop and how clean the place is."
United States
David M.
The price is AU$548
includes taxes & fees
21 Oct - 22 Oct
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park
Classy 3BR King Apt in The Grove
9.8 out of 10, Exceptional, (13)
"Perfect for a St Louis getaway!"
United States
Laura M.
The price is AU$301
includes taxes & fees
22 Oct - 23 Oct
Classy 3BR King Apt in The Grove
Renovated 3 Bedroom Home By StayLage!
2.0 star property
9.8 out of 10, Exceptional, (8)
"5 coaches stayed for 4 days and enjoyed our time. The home is comfortable and in a quiet neighborhood!"
United States
Ken S.
The price is AU$584
includes taxes & fees
21 Oct - 22 Oct
Renovated 3 Bedroom Home By StayLage!
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
9.8 out of 10, Exceptional, (45)
"We had a terrific time in St Louis!! The house was in a perfect location for us!! It was great!! Lots of great places to eat close by. Joe was wonderful and the place was excellent!! "
Canada
Shirley M.
The price is AU$304
includes taxes & fees
21 Oct - 22 Oct
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Classic Soulard 2BD King Master & Private Deck
9.8 out of 10, Exceptional, (50)
"This was a perfect place for our family of 4 for a quick few days in St. Louis. Close drive to the Arch. Very nice restaurants in the neighborhood within walking distance. Clean property and a safe neighborhood. "
United States
Kelly T.
The price is AU$299
includes taxes & fees
27 Oct - 28 Oct
Classic Soulard 2BD King Master & Private 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 AU$206 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, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Madison House 1 -Walk to Main St: This holiday home rental outside of Winchester is equipped with a pool table, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Magic House - St. Louis Children's Museum, or get outside and enjoy nature at Lou Fusz Soccer Complex. In the wider area, you’ll find Museum of Transportation and The Factory.

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.