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Our top choices for Winchester holiday rentals

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 £75
includes taxes & fees
8 Jul - 9 Jul
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

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 £110
includes taxes & fees
30 Jun - 1 Jul
6649 2E | Boutique Hotel Studio in Forest Park

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
9.4 out of 10, Exceptional, (11 reviews)
"Clean, convenient and satisfied our needs for this stay. "
United States
Michael L.
The price is £213
includes taxes & fees
24 Jun - 25 Jun
Settle into Soulard! 6 beds 2 full baths!

Cute town house with fenced backyard

Cute town house with fenced backyard
Barnhart
9.6 out of 10, Exceptional, (18 reviews)
"We stayed here while visiting family nearby. It met our needs. "
United States
Caren L.
The price is £212
includes taxes & fees
8 Jul - 9 Jul
Cute town house with fenced backyard

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, (159 reviews)
"Great location. Quiet neighborhood. Very convenient to downtown and other restaurants and fun locations. Easy parking. Very comfortable stay and host was super great! "
United States
Kelly R.
The price is £118
includes taxes & fees
24 Jun - 25 Jun
Centrally located in the Tower Grove East neighborhood!

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

Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony
The Gate
8.4 out of 10, Very good, (11 reviews)
"We absolutely ADORE this property! The location can’t be beat, parking is a breeze (you do have to figure out getting to it the first time), amenities are close and everything was clean and well-stocked. It IS on the 3rd floor up narrow stairs, but cute, Cute, CUTE!"
United States
April
The price is £139
includes taxes & fees
23 Jun - 24 Jun
Charming 1BR Retreat Opposite SSM SLU Hospital with Private Parking & Balcony

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

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Soulard
8.8 out of 10, Excellent, (18 reviews)
"We had a great experience. The place was clean and had a lot of character. The check in and check out process was easy. Dan had great communication with me. We walked to Miami Cafe around the corner and recommend it to anyone who stays here. The atmosphere and neighborhood had a lot of character. We enjoyed our stay!"
United States
Cheryl
The price is £148
includes taxes & fees
23 Jun - 24 Jun
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (36 reviews)
"Great location and communication from host!!"
United States
rachel l.
The price is £159
includes taxes & fees
23 Jun - 24 Jun
Starry Night | Steps to Tower Grove Park

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Beatiful home close to venues and shops. "
United States
Kelly H.
The price is £146
includes taxes & fees
13 Jul - 14 Jul
Stylish South City King 1BR Apt

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, (18 reviews)
"We had a great stay! The location is perfect- just a few blocks from tower grove park and right next to some great coffee shops. The property decoration is a little spartan, but we had everything we needed in a charming historic building. "
United States
Cole B.
The price is £165
includes taxes & fees
23 Jun - 24 Jun
Almond Blossoms at TG Park | Fenced Backyard+W/D

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (50 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
The price is £182
includes taxes & fees
29 Jun - 30 Jun
Top of Geyer apartment

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
St. Louis
9.4 out of 10, Exceptional, (9 reviews)
"This was absolutely perfect and reasonable pricing I surely will be back "
United States
David G.
The price is £78
includes taxes & fees
28 Jun - 29 Jun
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

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

Steps to TG Park+Grand | Free PK+WD+Pet Friendly
Tower Grove East
9.0 out of 10, Wonderful, (19 reviews)
"Very clean and cozy. Kitchen had everything I needed- really appreciated the coffee supplies!"
United States
Kelsey K.
The price is £142
includes taxes & fees
23 Jun - 24 Jun
Steps to TG Park+Grand | Free PK+WD+Pet Friendly

6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is £109
includes taxes & fees
13 Jul - 14 Jul
6649 1E | Garden Style Studio Near Forest Park

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (25 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is £116
includes taxes & fees
23 Jun - 24 Jun
6655 1N | Elegance Near the St. Louis Arch

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (49 reviews)
"Made us feel like we was at home nice place "
United States
Marshay M.
The price is £204
includes taxes & fees
6 Jul - 7 Jul
Convenience 2 Bedroom House to Explore All of St Louis

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck
Soulard
10.0 out of 10, Exceptional, (4 reviews)
"Great location to all Soulard has to offer."
United States
Lori H.
The price is £173
includes taxes & fees
28 Jun - 29 Jun
Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic place. "
United States
Andrew W.
The price is £154
includes taxes & fees
14 Jul - 15 Jul
Soulard King 1BR - Personal Gym and Sauna Oasis

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (65 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
The price is £155
includes taxes & fees
13 Jul - 14 Jul
Cozy Soulard 2BR w/ Free Parking

6653 1N | European Style Unit Near Forest Park

6653 1N | European Style Unit Near Forest Park
Dogtown
8.4 out of 10, Very good, (5 reviews)
"Good experience overall.. would recommend "
United States
orlando c.
The price is £124
includes taxes & fees
24 Jun - 25 Jun
6653 1N | European Style Unit Near Forest 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.
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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 £75 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?

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck: This holiday home rental outside of Winchester offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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 Sophia M. Sachs Butterfly House. In the wider area, you’ll find Castlewood State Park and Museum of Transportation.

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.