Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (71 reviews)
"Quiet and close to nature. "
United States
Andy
Adorable Guest Cabin In The Woods

Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (11 reviews)
"The Garden Cottage was a great little getaway spot!Very clean and had all the essentials!"
United States
Kyle J.
Cozy Cottage With a View in La Grange

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (9 reviews)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
Swiss Alp Texas Cabin

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (55 reviews)
"It was a very nice place to stay."
United States
Mike M.
Pinehaven Luxury Glamping

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, (20 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
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

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

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

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (59 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 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, (19 reviews)
"We had a great time in this treehouse."
United States
Tandy S.
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
8.4 out of 10, Very good, (5 reviews)
"Amenities were plentiful."
United States
Karen G.
Charming Cottage, 5 Minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.8 out of 10, Exceptional, (69 reviews)
"My daughter and I loved staying at Enchanting Casita! Such a cute little cottage and great location! Perfect place to relax after a long day of shopping in Round Top."
United States
Michelle L.
Enchanting Casita, 5 minutes to Round Top!

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (108 reviews)
"Clean, spacious, perfect for our needs. Always enjoy staying here. "
United States
Belinda A.
Charming & Cozy Victorian in Quiet Residential Setting

Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top
Fayette County
8.2 out of 10, Very good, (11 reviews)
"Great property, will stay again. "
United States
Jerry A.
Lakefront Charm: Your Perfect Getaway in Round Top

Premium Lakefront Cabin #1: The Armadillo (Austin)

Premium Lakefront Cabin #1: The Armadillo (Austin)
Bastrop
Premium Lakefront Cabin #1: The Armadillo (Austin)

Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful light and bright place to stay near RoundTop!!"
United States
Jennifer S.
Round Top Refuge Guest House

Spacious MCM home 2 minutes from downtown, Pet-Friendly!

Spacious MCM home 2 minutes from downtown, Pet-Friendly!
Smithville
9.6 out of 10, Exceptional, (15 reviews)
"We will absolutely stay here every time we're in the Austin area."
United States
Catherine K.
Spacious MCM home 2 minutes from downtown, Pet-Friendly!

Dodo's Place on 22 acres outside of Smithville, TX

Dodo's Place on 22 acres outside of Smithville, TX
Smithville
10.0 out of 10, Exceptional, (2 reviews)
"The host was great it cozy and peaceful would definitely stay here again when I am in the area"
United States
Cutter H.
Dodo's Place on 22 acres outside of Smithville, TX

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, (225 reviews)
"Well equipped, supplied and tastefully decorated. "
Singapore
William H.
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

Lost Pines Lake House near Bastrop State Park and Buescher State Park..

Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Smithville
9.2 out of 10, Wonderful, (35 reviews)
"We had very good and clean and comfortable accommodations. "
United States
Peter W.
Lost Pines Lake House near Bastrop State Park and Buescher State Park..

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.
Round Top Refuge Main House
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, 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$198 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?

Escape to Giddings - Charming 2-Bedroom Vacation Home: This holiday home rental outside of Winchester is located in a rural location, 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. Make the most of games in this rental home to help you unwind.

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 Tejas Lake. 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.