Winchester Holiday Rentals

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Adorable Guest Cabin In The Woods

9.8 out of 10, Exceptional, (55)
"Great stay in a nice, relaxing cabin"
The price is AU$210
includes taxes & fees
9 Sept - 10 Sept
Adorable Guest Cabin In The Woods

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (45)
"My girlfriend and I really enjoyed the property and the location. Everything about the stay was phenomenal and accommodating! Highly recommend!"
The price is AU$328
includes taxes & fees
8 Sept - 9 Sept
Pinehaven Luxury Glamping

Waterfront Smithville River House

9.8 out of 10, Exceptional, (60)
"We had a great time staying here as we explored the area. Property was as advertised, well kept, and very clean"
Waterfront Smithville River House

Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

10.0 out of 10, Exceptional, (104)
"Always have an awesome experience here! "
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

Charming & Cozy Victorian in Quiet Residential Setting

10.0 out of 10, Exceptional, (93)
"My mom and I enjoyed our stay; the house was clean, well stocked and in a good neighborhood. The owner was quick to respond to messages and had an easy check in and out process. "
The price is AU$351
includes taxes & fees
11 Sept - 12 Sept
Charming & Cozy Victorian in Quiet Residential Setting

Escape to Giddings - Charming 2-Bedroom Vacation Home

10.0 out of 10, Exceptional, (139)
"Relaxing and beautiful property "
Escape to Giddings - Charming 2-Bedroom Vacation Home

Fun, eclectic Round Top home w/POOL! 5 min to town

9.8 out of 10, Exceptional, (87)
"We had a wonderful stay at this charming, rustic antique home! The location was perfect—just minutes from town but tucked away in a peaceful country setting. The pool was absolutely lovely and made for relaxing afternoons. The whole place was quiet, cozy, and felt like a true home away from home. The beds were super comfortable too! Highly recommend for anyone looking for a restful and scenic getaway."
The price is AU$908
includes taxes & fees
8 Sept - 9 Sept
Fun, eclectic Round Top home w/POOL! 5 min to town

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (205)
"I love this little cottage. Smithville is such a beautiful place to visit. Cottage with pool makes you seem that you are at your own private resort.i always feel that i have had a relaxing vacation. "
Cottage with pool in historic downtown

Rustic Charm in our Quaint Round Top Farmhouse!

10.0 out of 10, Exceptional, (2)
"We loved out stay in the cooper house!"
The price is AU$485
includes taxes & fees
8 Sept - 9 Sept
Rustic Charm in our Quaint Round Top Farmhouse!

The White Magnolia Cottage

9.8 out of 10, Exceptional, (42)
"A wonderful place to stay with a perfect location"
The price is AU$325
includes taxes & fees
8 Sept - 9 Sept
The White Magnolia Cottage

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

10.0 out of 10, Exceptional, (211)
"Great place. Very comfortable. Only 10min to the lake. House had everything we needed. "
The price is AU$352
includes taxes & fees
9 Sept - 10 Sept
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

Charming Cottage, 5 Minutes to Round Top!

9.0 out of 10, Wonderful, (2)
"My daughter and I had a great time in Round Top . We did lots of shopping and eating in fine restaurants. The charming cottage we stayed at was clean and cozy. It was small , but efficient for our needs. Location was perfect. Cant wsit to come back in October when its cooler!"
The price is AU$297
includes taxes & fees
8 Sept - 9 Sept
Charming Cottage, 5 Minutes to Round Top!

Round Top entertainer's oasis w/POOL, Pond & more!

8.8 out of 10, Excellent, (6)
"This place was amazing! The two of us needed a weekend away and happy to have found this one. I was inspired to redecorate my house when we got back :) If you’re going when it’s cold-just make sure that the heat issue in the master room is resolved or that they have a heater in there, as we had some issues with that but the rest of the house was super cozy and warm. Would definitely recommend!"
The price is AU$1,041
includes taxes & fees
8 Sept - 9 Sept
Round Top entertainer's oasis w/POOL, Pond & more!

Swiss Alp Texas Cabin

9.8 out of 10, Exceptional, (7)
"Perfect place for a couple. Wish we could have stayed longer. Very thoughtful details and great decor. "
The price is AU$256
includes taxes & fees
8 Sept - 9 Sept
Swiss Alp Texas Cabin

Round Top Refuge Guest House

10.0 out of 10, Exceptional, (4)
"Great place to stay! "
The price is AU$288
includes taxes & fees
8 Sept - 9 Sept
Round Top Refuge Guest House

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

10.0 out of 10, Exceptional, (382)
"We loved everything about this property, from the comfort and extra touches in the home to the wonderful trails and accommodations for our dog."
The price is AU$327
includes taxes & fees
9 Sept - 10 Sept
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

9.8 out of 10, Exceptional, (93)
"Adventured from Florida to check-out Round Top TX and the antique extravaganza … this quaint country cottage , was centrally located to all the surrounding cities. It was very quiet and offered what we needed for the stay. "
The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

Steps away from the sweet LaGrange downtown square

8.6 out of 10, Excellent, (4)
"We loved our stay at this house! The location was easily walkable to downtown and in a great neighborhood. "
The price is AU$718
includes taxes & fees
1 Oct - 2 Oct
Steps away from the sweet LaGrange downtown square

Round Top Gem | Casa Tres Hermanas | Pool + Hot Tub + Fire Pit + Grill

9.6 out of 10, Exceptional, (20)
"Very nice place that is well maintained. Will certainly stay again when visiting the area."
Round Top Gem | Casa Tres Hermanas | Pool + Hot Tub + Fire Pit + Grill
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

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$210 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?

Charming & Cozy Victorian in Quiet Residential Setting: This holiday home rental outside of Winchester offers a garden, a selection of books and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Boat Lake. In the wider area, you’ll find Zula B Wylie Library and Bluff Creek Ranch.

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.