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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday rentals

A covered outdoor area with a gravel floor, surrounded by trees and a body of water.

1. Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse

Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
Smithville
The price is AU$102
includes taxes & fees
28 Sept - 29 Sept
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
A hot tub with a wooden deck, a metal roof, and a view of a natural landscape.

2. 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, (6 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$222
includes taxes & fees
28 Sept - 29 Sept
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
A hot tub with a wooden deck, a metal roof, and a view of a natural landscape.

3. 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, (7 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
The price is AU$263
includes taxes & fees
28 Sept - 29 Sept
Dodo's Place on 22 acres outside of Smithville, TX
A view of a lake with surrounding greenery and a clear sky.

4. Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (17 reviews)
"Megan is a wonderful host, we enjoyed our stay!"
United States
Leeann
The price is AU$226
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage With a View in La Grange
A compact RV interior with a kitchenette, a seating area, and a small dining table.

5. Riverside Romance/Luxury RV/Starry Skies & S'mores

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (72 reviews)
"Very peaceful and clean"
United States
Lauren S.
The price is AU$240
includes taxes & fees
30 Sept - 1 Oct
Riverside Romance/Luxury RV/Starry Skies & S'mores
A historic building with a symmetrical facade, arched windows, and a central entrance with a balcony.

6. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (115 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
The price is AU$283
includes taxes & fees
4 Oct - 5 Oct
Charming & Cozy Victorian in Quiet Residential Setting
A living room with a sofa, a bed, a dining area, and a kitchen.

7. 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, (40 reviews)
"It was quiet and secluded. We were able to sit back and relax after hiking all day. I would rent this house again."
United States
Theresa
The price is AU$335
includes taxes & fees
5 Oct - 6 Oct
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
A campfire with a picnic table nearby, surrounded by trees and a body of water.

8. Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4 reviews)
"The property is beautiful and the RV is very clean. There are tons of amenities. We enjoyed watching the cardinals and humming birds!"
United States
Kimberly
The price is AU$273
includes taxes & fees
6 Oct - 7 Oct
Romance Glamping | Pup Paradise | Near River | ADA
A living room with a sofa, a round coffee table, and a lamp.

9. The Lucy | Sweet Retreat for 2-4 Near Ice Plant

The Lucy | Sweet Retreat for 2-4 Near Ice Plant
La Grange
10.0 out of 10, Exceptional, (1 review)
"Lovely home close to round top! House was well equipped with everything we needed. Bed and sofa sleeper were very comfortable. "
United States
Erin M.
The price is AU$521
includes taxes & fees
5 Oct - 6 Oct
The Lucy | Sweet Retreat for 2-4 Near Ice Plant
A modern kitchen with a black sink, a coffee machine, and a dining area with wicker chairs and a round table.

10. 2nd Floor Loft Across from Ice Plant | The Otis

2nd Floor Loft Across from Ice Plant | The Otis
La Grange
10.0 out of 10, Exceptional, (6 reviews)
"stayed here with my mom, aunt and sister-in-law for a girls trip for round top! slept 4 comfortably, honestly had plenty of room. location was perfect for us, just a little over 20 min drive to the trade shows and conveniently there was a HEB practically across the street for any necessities ! would def stay here again. "
United States
Hunter L.
The price is AU$521
includes taxes & fees
5 Oct - 6 Oct
2nd Floor Loft Across from Ice Plant | The Otis
A bedroom with a sloped ceiling, a chandelier, a bed with a wooden headboard, a patterned rug, and a window with a view.

11. Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (10 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
28 Sept - 29 Sept
Swiss Alp Texas Cabin
A wooden playground with a slide, climbing area, and swings.

12. 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
10.0 out of 10, Exceptional, (22 reviews)
"A wonderful place to stay while we attended the AKC hunt trials. Dry clean & had everything we needed. We also spent a relaxing, rainy evening watching a movie."
United States
Jacque H.
The price is AU$435
includes taxes & fees
29 Sept - 30 Sept
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
A wooden cabin with a blue roof, surrounded by a wooden deck and metal railings, set in a forested area.

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

The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time and everything we needed was available. "
United States
Jenna H.
The price is AU$289
includes taxes & fees
28 Sept - 29 Sept
The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
A living room with a white sofa, a grey armchair, a dining table with wicker chairs, and a small side table with a lamp.

14. Porch Swing Vibes for 4 | Francis @ Grace Inn

Porch Swing Vibes for 4 | Francis @ Grace Inn
La Grange
10.0 out of 10, Exceptional, (4 reviews)
"Awesome stay, very convenient and cute "
United States
Christie B.
The price is AU$671
includes taxes & fees
5 Oct - 6 Oct
Porch Swing Vibes for 4 | Francis @ Grace Inn
A wooden staircase leading to a cabin with a wooden exterior and a wooden deck.

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

The Hobbit's Nest Treehouse, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (238 reviews)
"Incredibly charming one of a kind experience, kids loved the woodland details and felt like stepping on to a movie set. Excellent host communication, we felt like guests in the true sense of the word."
United States
Gavin
The price is AU$289
includes taxes & fees
29 Sept - 30 Sept
The Hobbit's Nest Treehouse, A Magical Dog-friendly Treehouse in the Lost Pines Shire
A dining table set with a cake, teapot, cups, and a vase of flowers.

16. The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (66 reviews)
"Beautiful cottage, it was perfect for us!"
United States
Amy
The price is AU$309
includes taxes & fees
28 Sept - 29 Sept
The White Magnolia Cottage
A reception desk with a colorful striped wall, a large number '6' sign, and a blue informational sign.

17. 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds|Nsmk,Kitchen
Giddings TX
10.0 out of 10, Exceptional, (359 reviews)
"Awesome value for what we got, it was perfect for a weekend getaway!"
United States
Anonymous traveller
The price is AU$228
includes taxes & fees
28 Sept - 29 Sept
2 Queen Beds|Nsmk,Kitchen
A dining area with a wooden table, four wicker chairs, a chandelier, and a blue and white vase with flowers.

18. Bridal Ready + Southern Charm | The Moli

Bridal Ready + Southern Charm | The Moli
La Grange
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful place to stay. Loved the decor. Can't wait to stay again."
United States
Trisha T.
The price is AU$748
includes taxes & fees
5 Oct - 6 Oct
Bridal Ready + Southern Charm | The Moli
A two-story house with a covered patio area, outdoor seating, and a dog.

19. Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
9.8 out of 10, Exceptional, (10 reviews)
"Fabulous stay, can’t wait to come back!"
United States
Karin C.
The price is AU$557
includes taxes & fees
29 Sept - 30 Sept
Round Top Refuge Guest House
A wooden deck with a railing, a bench, and a table with chairs.

20. 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, (403 reviews)
"Amazing location and just a great cabin. "
United States
Sean H.
The price is AU$306
includes taxes & fees
28 Sept - 29 Sept
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
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

Walk to Lake + Stock Tank Pool + Fire Pit

Walk to Lake + Stock Tank Pool + Fire Pit

10/10 Excellent
"This was our second stay and it was just as good as the first. The house is tucked back in the pines and feels completely secluded. Everything was spotless and thoughtfully put together, and it's even prettier in person than in the photos. The hosts were so communicative and gracious, which made everything easy. We're planning to make this an annual trip!"
Brooke P. 2-night trip
Posted 3 hours ago
Walk to Lake + Stock Tank Pool + Fire Pit

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$240 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?

Walk to Lake + Stock Tank Pool + Fire Pit: This holiday home rental outside of Winchester is located on a lake, and has an outdoor pool, a fireplace 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. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.