Default HTG hotel image

Search Holiday Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • 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 £113
includes taxes & fees
24 Sept - 25 Sept
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

2. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (41 reviews)
"Great spot!"
United States
Anonymous traveller
The price is £55
includes taxes & fees
30 Sept - 1 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

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

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (19 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 £137
includes taxes & fees
21 Sept - 22 Sept
Chic Minimalist Gem w/ Fenced Backyard + W/D

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

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.2 out of 10, Good, (14 reviews)
"Great place. Clean and spacious"
United States
Isai
The price is £129
includes taxes & fees
21 Sept - 22 Sept
Safe and private apt-Near Forest Park-Free parking

5. 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 £192
includes taxes & fees
21 Sept - 22 Sept
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

6. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.4 out of 10, Exceptional, (40 reviews)
"Fantastic place!"
United States
Anonymous traveller
The price is £55
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking, Kitchen

7. 6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
The price is £109
includes taxes & fees
30 Sept - 1 Oct
6649 2E | Boutique Hotel Studio in Forest Park

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

Irises at TG Park | Fenced Backyard+W/D+Storage
Tower Grove South
9.2 out of 10, Wonderful, (17 reviews)
"The apartment was just what we needed Perfect for a weekend getaway "
United States
Robert W.
The price is £145
includes taxes & fees
20 Oct - 21 Oct
Irises at TG Park | Fenced Backyard+W/D+Storage

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

6647 1W | Quaint Studio in Central St. Louis
Dogtown
8.2 out of 10, Very good, (28 reviews)
"Great location, secure parking, overall great stay "
United States
Marcus
The price is £108
includes taxes & fees
21 Sept - 22 Sept
6647 1W | Quaint Studio in Central St. Louis

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

Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (16 reviews)
"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"
United States
Chris B.
The price is £206
includes taxes & fees
4 Oct - 5 Oct
Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

11. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
8.0 out of 10, Very good, (31 reviews)
"Great place to stay for the weekend. Cute and clean. Nice area with lot's of places in walking distance. I will definitely stay again."
United States
Brigitte B.
The price is £115
includes taxes & fees
24 Sept - 25 Sept
6655 1N | Elegance Near the St. Louis Arch

12. Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (177 reviews)
"Great place!"
United States
Arthur S.
The price is £117
includes taxes & fees
21 Sept - 22 Sept
Centrally located in the Tower Grove East neighborhood!

13. 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, (22 reviews)
"Great location, responsive host & perfect for our short stay! "
United States
Bekah K.
The price is £126
includes taxes & fees
21 Sept - 22 Sept
Charming Tower Grove Flat-Steps to T.G Park+Grand

14. 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, (52 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is £204
includes taxes & fees
27 Sept - 28 Sept
Convenience 2 Bedroom House to Explore All of St Louis

15. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

2 Queen Beds | Mobil Access Tub Nsmk Kitchen
Westport
9.8 out of 10, Exceptional, (45 reviews)
"Great place to stay!"
United States
Anonymous traveller
The price is £55
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Mobil Access Tub Nsmk Kitchen

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

Almond Blossoms at TG Park | Fenced Backyard+W/D
Tower Grove South
9.8 out of 10, Exceptional, (22 reviews)
"Enjoyed our stay and loved how close to park it was located."
United States
Pam Y.
The price is £141
includes taxes & fees
28 Sept - 29 Sept
Almond Blossoms at TG Park | Fenced Backyard+W/D

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

Charming 1-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 £84
includes taxes & fees
23 Sept - 24 Sept
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

18. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (155 reviews)
"Staff was great and accommodating to my needs."
United States
Triman
The price is £93
includes taxes & fees
28 Sept - 29 Sept
White House at Grand Central

19. 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 £122
includes taxes & fees
21 Sept - 22 Sept
6649 1W | Beautiful Getaway in Central St. Louis

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

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (199 reviews)
"Great cottage, pet friendly, wonderful neighborhood to explore and many great food options within walking distance. Would definitely stay again at this cottage."
United States
Scott J.
The price is £120
includes taxes & fees
30 Sept - 1 Oct
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
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 £55 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.