Winchester Holiday Rentals from NZ$119: Search Short-Term Rentals

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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

Ballwin

Keith K.

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a dining table, sofa, and a large window with blinds.

2. Stunning Minimalist Gem | Fenced Backyard + W/D

Princeton Heights

Christopher

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

Dogtown

Andrew T.

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

4. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Westport

Anonymous traveller

includes taxes & fees

1 Nov - 2 Nov

A living room with a green sofa, a wooden coffee table, and hanging plants.

5. Safe and private apt-Near Forest Park-Free parking

Dogtown

Machelle

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

Princeton Heights

Dave

includes taxes & fees

15 Oct - 16 Oct

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!

Eureka

Keith

includes taxes & fees

20 Oct - 21 Oct

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

St. Peters

Chris B.

includes taxes & fees

18 Oct - 19 Oct

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Top Winchester Hotel Reviews

21C Museum Hotel St Louis

10/10 Excellent

"Wifi unfortunately didn’t work in our room but the other amenities made up for it. If you don’t want to use valet, plan out your parking prior. Besides that everything was awesome."

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

10/10 Excellent

"This hotel is located in a great location, close to the Gateway Arch and the ballpark where the Cardinals play. There were numerous fun restaurants within walking distance, and we felt safe except down by the Old Spaghetti Factory. I would stay in this hotel again and recommend it to others."

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent

"The property itself was maintained ok. It does need to be updated as the carpets and bathrooms are old. Our ceiling in the bathroom was peeling due to the humidity from the shower over the years. The carpet in the rooms and common areas is older. As for the staff everyone was nice and did what was expected of them. I would use this property again to stay as it’s walking distance from everything downtown."

Clayton Plaza Hotel & Extended Stay

8/10 Good

"Hotel staff were excellent, friendly, professional and by far the best reason to re-book. The hotel itself was very clean, located near professional buildings/courts and some eateries within walking distance. The room was clean as well and nicely proportioned with some of the best mattresses/bedding I've experienced. Only slight downside was the breakfast bar--the food and choices were ample and very good (especially the made to order omelets and waffles) but the setting was less than clean and rather worn--not in keeping with the rest of the hotel. All in all, a great place to stay and would definitely book again."

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$119 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 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.

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Check prices for these dates

Our top choices for Winchester holiday rentals

1. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

2. Stunning Minimalist Gem | Fenced Backyard + W/D

3. 6653 1S | Beautiful Unit Near Forest Park

4. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

5. Safe and private apt-Near Forest Park-Free parking

6. Chic Minimalist Gem w/ Fenced Backyard + W/D

7. Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

8. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

9. 6655 1N | Elegance Near the St. Louis Arch

10. 6653 1N | European Style Unit Near Forest Park

11. Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

12. White House at Grand Central

13. Convenience 2 Bedroom House to Explore All of St Louis

14. 6649 1E | Garden Style Studio Near Forest Park

15. 6653 2S | Jewel of Central St. Louis

16. 6649 1W | Beautiful Getaway in Central St. Louis

17. Charming Byrnes Mill Retreat with WiFi & Fenced Backyard.

18. 3BR Dogtown Bungalow |Office + Bar

19. Steps to TG Park+Grand | Free PK+WD+Pet Friendly

20. Centrally located in the Tower Grove East neighborhood!

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

21C Museum Hotel St Louis

Pear Tree Inn St. Louis Airport

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Courtyard by Marriott St. Louis Downtown/Convention Center

Pear Tree Inn St. Louis Near Union Station

Clayton Plaza Hotel & Extended Stay

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis Union Station

Moonrise Hotel

Find out more about Winchester

Frequently asked questions

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