Default HTG hotel image

Holiday Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester holiday rentals

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

Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Ballwin
7.8 out of 10, Good, (24 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
The price is €135
includes taxes & fees
26 Oct - 27 Oct
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

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

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.6 out of 10, Good, (17 reviews)
"I loved that it was in an older building and there is history there. The best were comfortable, and the apartment was spotless."
United States
Machelle
The price is €155
includes taxes & fees
26 Oct - 27 Oct
Safe and private apt-Near Forest Park-Free parking

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

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
9.8 out of 10, Exceptional, (31 reviews)
"Nice area, very well kept house and easy check-in process. Good parking"
United States
Christopher
The price is €164
includes taxes & fees
27 Oct - 28 Oct
Stunning Minimalist Gem | Fenced Backyard + W/D

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

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (21 reviews)
"Very nice, clean, modern apartment in a safe, quiet, suburban neighborhood. We were very happy with our stay there for our visit to WashU and St. Louis."
United States
Dave
The price is €164
includes taxes & fees
27 Oct - 28 Oct
Chic Minimalist Gem w/ Fenced Backyard + W/D

5. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.4 out of 10, Exceptional, (43 reviews)
"Great spot!"
United States
Anonymous traveller
The price is €61
includes taxes & fees
29 Oct - 30 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

6. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (34 reviews)
"I loved the security aspect of this rental. Felt very safe and it is very close to Forest park which is amazing"
United States
heather d.
The price is €138
includes taxes & fees
26 Oct - 27 Oct
6655 1N | Elegance Near the St. Louis Arch

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

Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
Eureka
9.0 out of 10, Wonderful, (72 reviews)
"This was an extraordinary experience with great property and location and the description of the property was exact on. The host was very helpful when it came to anything we was needing very much appreciated and look forward to staying with this property owner again."
United States
Keith
The price is €227
includes taxes & fees
9 Nov - 10 Nov
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

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

Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (8 reviews)
"Thank you we enjoyed the place but we would like to get some more nights if all possible"
United States
Tommy H.
The price is €109
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

9. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (167 reviews)
"Nice find in the city"
United States
Mark
The price is €110
includes taxes & fees
1 Nov - 2 Nov
White House at Grand Central

10. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"Hot water was an issue. Other than that great place to stay"
United States
Ashley C.
The price is €138
includes taxes & fees
29 Oct - 30 Oct
6653 2S | Jewel of Central St. Louis

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

Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (20 reviews)
"What a great place to stay! Clean, well stocked, and very spacious. Would definitely book again."
United States
Lynn D.
The price is €264
includes taxes & fees
26 Oct - 27 Oct
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

12. Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.0 out of 10, Wonderful, (25 reviews)
"Great location, responsive host & perfect for our short stay! "
United States
Bekah K.
The price is €156
includes taxes & fees
26 Oct - 27 Oct
Charming Tower Grove Flat-Steps to T.G Park+Grand

13. 6649 1W | Beautiful Getaway in Central St. Louis

6649 1W | Beautiful Getaway in Central St. Louis
Dogtown
7.2 out of 10, Good, (12 reviews)
"The apt"
United States
Pantung
The price is €147
includes taxes & fees
26 Oct - 27 Oct
6649 1W | Beautiful Getaway in Central St. Louis

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

Steps to TG Park+Grand | Free PK+WD+Pet Friendly
Tower Grove East
9.2 out of 10, Wonderful, (26 reviews)
"It was very clean. The location was near everything to do."
United States
William H.
The price is €159
includes taxes & fees
26 Oct - 27 Oct
Steps to TG Park+Grand | Free PK+WD+Pet Friendly

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

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (54 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is €243
includes taxes & fees
25 Oct - 26 Oct
Convenience 2 Bedroom House to Explore All of St Louis

16. Spotless Cozy Gem: 5 Star Location, Yard, Gym, Family Friendly

Spotless Cozy Gem: 5 Star Location, Yard, Gym, Family Friendly
Clifton Heights
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay! The location was perfect. Very clean and very easy to check- in! Very cozy!"
United States
Emily R.
Spotless Cozy Gem: 5 Star Location, Yard, Gym, Family Friendly

17. Historic Main Street Studio | Dog-Friendly

Historic Main Street Studio | Dog-Friendly
St. Charles Historic District
9.2 out of 10, Wonderful, (40 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
The price is €195
includes taxes & fees
25 Oct - 26 Oct
Historic Main Street Studio | Dog-Friendly

18. Top of Geyer :Modern Condo in Center of Historical Soulard— Walk score 87

Top of Geyer :Modern Condo in Center of Historical Soulard— Walk score 87
Soulard
9.6 out of 10, Exceptional, (58 reviews)
":-)"
United States
THOMAS E
The price is €226
includes taxes & fees
26 Oct - 27 Oct
Top of Geyer :Modern Condo in Center of Historical Soulard— Walk score 87

19. Walk to Main | Pet-Friendly Yard & Workspace

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
The price is €237
includes taxes & fees
25 Oct - 26 Oct
Walk to Main | Pet-Friendly Yard & Workspace

20. 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
9.0 out of 10, Wonderful, (38 reviews)
"We enjoyed our stay, very quaint house and Julie was an amazing host "
United States
Lori O.
The price is €230
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

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 €61 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.