Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (10 reviews)
"Very nice retreat to stay in the La Grange area. The property couldn’t be more beautiful. The coffee they stock is amazing as well. "
United States
Andrew W.
The price is AU$237
includes taxes & fees
2 Mar - 3 Mar
Cozy Cottage With a View in La Grange

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (8 reviews)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
The price is AU$239
includes taxes & fees
9 Feb - 10 Feb
Swiss Alp Texas Cabin

Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Paige
9.8 out of 10, Exceptional, (19 reviews)
"The property at Blessing Ranch in Paige, Tx was Very relaxing and peaceful. Not too far from dining and shopping, yet off the main road for privacy. The house is immaculate with all modern finishes and appliances. Very comfortable beds. Exceeded my expectations."
United States
Richard
The price is AU$451
includes taxes & fees
11 Feb - 12 Feb
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

Elm Grove Camper- Less than 3 miles from Round Top proper

Elm Grove Camper- Less than 3 miles from Round Top proper
Round Top
9.6 out of 10, Exceptional, (27 reviews)
"This is our 3rd time staying with this host for the fall antique show and have had a pleasant stay each time. "
United States
Shawna M.
The price is AU$311
includes taxes & fees
9 Feb - 10 Feb
Elm Grove Camper- Less than 3 miles from Round Top proper

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (70 reviews)
"We stayed here last year also. It's only 3 miles from relatives we were visiting, so very handy. Nothing fancy, but clean & quite."
United States
Barbara L.
The price is AU$196
includes taxes & fees
9 Feb - 10 Feb
Adorable Guest Cabin In The Woods

Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (6 reviews)
"The guest house was perfect. Nice space and beautiful furnishings. Very comfortable beds location was easy to get to Round Top"
United States
renebene**
The price is AU$444
includes taxes & fees
9 Feb - 10 Feb
Round Top Refuge Guest House

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (390 reviews)
"This was our third visit here and we just loved it!!! Such a relaxing getaway, we will be back for sure!"
United States
Lyn M.
The price is AU$289
includes taxes & fees
9 Feb - 10 Feb
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (52 reviews)
"Great location for the Round Top Antiques Fair. Stayed only for a night but enjoyed our stay, hopefully will be back again! "
United States
Hannah M.
The price is AU$311
includes taxes & fees
9 Feb - 10 Feb
The White Magnolia Cottage

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (18 reviews)
"We had a great time in this treehouse."
United States
Tandy S.
The price is AU$304
includes taxes & fees
9 Feb - 10 Feb
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Smithville
9.0 out of 10, Wonderful, (2 reviews)
"I was out here on a work trip - great location for a quick trip. Just the correct size for one person. And the goats are amazing!!!"
United States
Jim C.
The price is AU$223
includes taxes & fees
9 Feb - 10 Feb
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat

Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top
Fayette County
8.8 out of 10, Excellent, (10 reviews)
"Great property, will stay again. "
United States
Jerry A.
The price is AU$363
includes taxes & fees
9 Feb - 10 Feb
Lakefront Charm: Your Perfect Getaway in Round Top

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (232 reviews)
"Fantastic stay! The treehouse is quite charming with thoughtful Tolkien touches. The property is secluded and makes you feel as though you have the place all to yourself. Would definitely stay again!"
United States
Allen L.
The price is AU$333
includes taxes & fees
9 Feb - 10 Feb
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
9.0 out of 10, Wonderful, (4 reviews)
"Amenities were plentiful."
United States
Karen G.
The price is AU$283
includes taxes & fees
9 Feb - 10 Feb
Charming Cottage, 5 Minutes to Round Top!

Historical country cabin in Round Top!

Historical country cabin in Round Top!
Fayette County
6.6 out of 10, (4 reviews)
"The cabin was cute and clean and in a great location. The problem we had was the portable AC unit did not cool sufficiently. The 2nd bedroom is not a bedroom it is a loft with a ladder that is not safe to climb. "
United States
Christa W.
The price is AU$280
includes taxes & fees
17 Feb - 18 Feb
Historical country cabin in Round Top!

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (106 reviews)
"Such a beauty of a house! Highly recommend staying here if you are ever in Bastrop for the night! "
United States
Jim C.
The price is AU$330
includes taxes & fees
9 Feb - 10 Feb
Charming & Cozy Victorian in Quiet Residential Setting

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (53 reviews)
"It was a very nice place to stay."
United States
Mike M.
The price is AU$311
includes taxes & fees
9 Feb - 10 Feb
Pinehaven Luxury Glamping

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (221 reviews)
"Only stayed one night as a stop over for a road trip to Port Aransas. Clean, quiet and secluded....just how I like it. Would stay again for longer."
United States
Kevin M.
The price is AU$360
includes taxes & fees
16 Feb - 17 Feb
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

Round Top Refuge Main House

Round Top Refuge Main House
La Grange
10.0 out of 10, Exceptional, (3 reviews)
"Very Clean, Amazing Host, Wonderful location! Would definitely stay again!!"
United States
Colby W.
The price is AU$415
includes taxes & fees
10 Feb - 11 Feb
Round Top Refuge Main House

Delightful Cabin with AC in cozy Smithville

Delightful Cabin with AC in cozy Smithville
Smithville
The price is AU$240
includes taxes & fees
9 Feb - 10 Feb
Delightful Cabin with AC in cozy Smithville
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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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 favourite 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 depend 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 AU$196 per night. Entering your travel dates in the search wizard might find you 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 a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Jersey Barnyard, or get out into nature at a spot like Mid Town Lee Smith Park. In the wider area, you’ll find Bluff Creek Ranch and Buescher State Park.

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 offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.