Winchester Holiday Rentals from NZ$226: Search Short-Term Rentals

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Our top choices for Winchester holiday rentals

Serenity Log Inn -Log out and Log Inn to Serenity

Imperial

dennis m.

includes taxes & fees

21 Apr - 22 Apr

Classy Midtown 3BR, King Master

The Gate

Kevin M.

includes taxes & fees

19 Apr - 20 Apr

Cute town house with fenced backyard

Barnhart

"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. "

Terry

includes taxes & fees

26 Apr - 27 Apr

Spacious & Centrally Located Apt (Sleeps 8)

The Gate

Jennifer L.

includes taxes & fees

15 Apr - 16 Apr

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

Bevo Mill

Michelle O.

includes taxes & fees

14 Apr - 15 Apr

scent-free stay - spacious , big yard and safe neighborhood

Imperial

Kim T.

includes taxes & fees

21 Apr - 22 Apr

Fragrance free - spacious Ranch -safe &quiet- 4 br 2 bath

High Ridge

Frank G.

includes taxes & fees

19 Apr - 20 Apr

3BR Dogtown Bungalow |Office + Bar

Dogtown

Greg H.

includes taxes & fees

12 May - 13 May

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Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent

"An older but highly maintained and high quality property. Very clean. Staff was exceptional to a person, friendly and responsive. Front desk attendant, Ollie was a jewel, she was friendly, efficient and very helpful. Beds were very comfortable, shower was great. They have both a complimentary dinner and a complimentary breakfast. Both were really great and exceeded expectations. The dinner even included an open bar for up to 3 alcoholic beverages gratis. There is a 24/7 coffee bar also. The location was just around the corner from the gateway Arch national park and within very close walk to the Cardinals baseball park. We were not out late after dark but did feel very comfortable walking in the downtown neighborhood near the property. The property and the parking garage are very secure with controlled access. The garage is quite tight, even a little Honda CRV has some difficulty with the tight spaces, a big F-150 would have a very difficult time negotiating the garage space. There is a $32 parking fee, with full in and out privileges; this is pretty much baseline for downtown parking. We happened to arrive on a baseball game evening, this caused the one night stay cost to be significantly above the usual cost."

Hyatt Regency St. Louis at The Arch

6/10 Okay

"Three out of 4 elevators were down on one side with no notice. After waiting for awhile, 20 or more minutes we decided to walk 16 flights of stairs with luggage, so we could get the our event on time. When brought up, we were just told yeah we’re working on it, no sorry or anything. Consider putting up signs so people know. "

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

6/10 Okay

"Breakfast was average but only had it one day because kids running all over area knocking into table, staff not too friendly, never got room cleaned for some reason and had to ask for everything- towels were in short supply and had long hair on every one I used - yuck- and really wanted to use pool and hot tub was brown and I think/hope they were about to clean it but we never went back to check - so disappointed. "

21C Museum Hotel St Louis

6/10 Okay

"Staff at the desk was pleasant, but not able to handle issues or concerns independently, stating they would have to wait to notify management on Monday because it was a weekend. My room had a broken door lock with exposed wires showing, the curtains had something on them (vomit maybe?), and there was a poorly patched area on the ceiling above the shower that appeared to be covering mold. One elevator remained out of service and the other two were very small and it took multiple attempts to be able to use an elevator. Food was good at the small cafe, but the service was slow and not very efficient, which required us to wait 45 minutes for an egg sandwich. The valet parking pricing was misleading, when we asked how much it would be to park until Sunday we were told $50. It was actually over $100. Other parking options were unclear. Valet staff was very pleasant. The museum was neat, overall the staff was pleasant and the lobby was unique and inviting. The room was good sized. "

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 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 NZ$226 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 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 Kirkwood 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.

Winchester Holiday Rentals

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Check prices for these dates

Our top choices for Winchester holiday rentals

Serenity Log Inn -Log out and Log Inn to Serenity

Classy Midtown 3BR, King Master

Cute town house with fenced backyard

Spacious & Centrally Located Apt (Sleeps 8)

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

scent-free stay - spacious , big yard and safe neighborhood

Fragrance free - spacious Ranch -safe &quiet- 4 br 2 bath

3BR Dogtown Bungalow |Office + Bar

Top of Geyer apartment

Old North Shanty/ Historic 1888 Brick Home Near Downtown St. Louis

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

Classic Soulard 2BD King Master & Private Deck

Pet-Friendly 1BR Apartment

Smoke Free!!The Rock House Bnb, StL. Centrally Located + Park. 8 person Max!

Lots of Space! Central to St Charles and STL. Newly Remodeled. Large Backyard!

Settle into Soulard! 6 beds 2 full baths!

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

Tiny Cottage - Big Loft

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

Charming open 4bd and screen-in porch! Sleeps 10!

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis at the Arch

Find out more about Winchester

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