Winchester Holiday Rentals from €63: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

A set of stone steps leading to a garage with a car parked inside.

1. Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

Ballwin

alex h.

includes taxes & fees

13 Sept - 14 Sept

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. Charming 3-bedroom house in delightful Ballwin and basement is not included

Ballwin

Stephanie N.

includes taxes & fees

7 Sept - 8 Sept

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

3. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Westport

Anonymous traveller

includes taxes & fees

14 Sept - 15 Sept

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

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

Princeton Heights

Christopher

includes taxes & fees

9 Sept - 10 Sept

A brown door with a glass panel, a potted plant, and a doormat.

5. Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

Eureka

Tina S.

includes taxes & fees

7 Sept - 8 Sept

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

A kitchen with a view to a patio, a refrigerator, and a trash can.

7. Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

St. Peters

Ruth R.

includes taxes & fees

7 Sept - 8 Sept

A bedroom with a large bed, a bedside table, a chair, a desk, a mirror, and a door.

8. 6649 2E | Boutique Hotel Studio in Forest Park

Dogtown

Marie

includes taxes & fees

29 Sept - 30 Sept

A bedroom with a bed, a dresser, and a nightstand. There is a hallway leading to a bathroom and a kitchen.

9. 6647 1W | Quaint Studio in Central St. Louis

Dogtown

Marcus

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a refrigerator. There is a dining table with chairs and a ceiling fan.

10. Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

The Hill

Crystal

includes taxes & fees

7 Sept - 8 Sept

A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

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

University City

Anna M.

includes taxes & fees

27 Sept - 28 Sept

A bedroom with a bed, bedside table, and a large painting on the wall.

12. 6649 1E | Garden Style Studio Near Forest Park

Dogtown

Dhgirlie H.

A spacious living room with hardwood flooring, a ceiling fan, a wooden dining table with benches, a sofa, and a coffee table.

13. Almond Blossoms at TG Park | Fenced Backyard+W/D

Tower Grove South

Pam Y.

includes taxes & fees

9 Sept - 10 Sept

14. Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Imperial

Tommy H.

includes taxes & fees

9 Sept - 10 Sept

A hotel lobby with a staircase, a reception desk, and a chandelier.

15. 2 Queen Beds | Non-Smoking, Kitchen

Westport

Anonymous traveller

includes taxes & fees

14 Sept - 15 Sept

A spacious foyer with a grand staircase, a piano, and a large rug.

16. White House at Grand Central

Grand Center

Triman

includes taxes & fees

7 Sept - 8 Sept

A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

17. 6653 2S | Jewel of Central St. Louis

Dogtown

"The apartment was conveniently located within walking distance of many attractions in Forest Park, and several bus lines for those who are inclined to explore the city via public transit. The apartment provided a good amount of space for two people. We really appreciated the free passes that were offered. We did, however, experience a number of issues during our stay. One warning to potential renters: if you need a quiet bedroom for sleeping, this may not be the property for you. Both the wood...

Susan

includes taxes & fees

7 Sept - 8 Sept

A living room with a sofa, armchair, coffee table, and a TV.

18. 6649 1W | Beautiful Getaway in Central St. Louis

Dogtown

Pantung

includes taxes & fees

7 Sept - 8 Sept

A spacious living area with a dining table, chairs, a sofa, and a ceiling fan.

19. Irises at TG Park | Fenced Backyard+W/D+Storage

Tower Grove South

Robert W.

20. 6655 1N | Elegance Near the St. Louis Arch

Dogtown

Brigitte B.

includes taxes & fees

14 Sept - 15 Sept

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis at the Arch

8/10 Good

"Nice hotel, the parking cost is outrageous $32.00 to park in hotel parking. I will not stay at this location 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, 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 €63 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester holiday rentals

1. Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

2. Charming 3-bedroom house in delightful Ballwin and basement is not included

3. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

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

5. Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

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

7. Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

8. 6649 2E | Boutique Hotel Studio in Forest Park

9. 6647 1W | Quaint Studio in Central St. Louis

10. Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

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

12. 6649 1E | Garden Style Studio Near Forest Park

13. Almond Blossoms at TG Park | Fenced Backyard+W/D