Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winchester holiday rentals

A cabin with a deck, outdoor seating, and a view of a forest.

1. Cozy Studio Cottage on 22 Acres

Cozy Studio Cottage on 22 Acres
Smithville
9.2 out of 10, Wonderful, (7 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$214
includes taxes & fees
23 Nov - 24 Nov
Cozy Studio Cottage on 22 Acres
A covered outdoor area with a gravel floor, surrounded by trees and a body of water.

2. 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$128
includes taxes & fees
13 Nov - 14 Nov
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
A compact, rustic cabin interior with a loft bedroom, a dining area with a table set for two, and a TV mounted on the wall.

3. Dodo's Place - Tiny Home on 22 Acres

Dodo's Place - Tiny Home on 22 Acres
Smithville
10.0 out of 10, Exceptional, (10 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
The price is AU$256
includes taxes & fees
17 Nov - 18 Nov
Dodo's Place - Tiny Home on 22 Acres
A compact RV interior with a kitchenette, a seating area, and a small dining table.

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (73 reviews)
"Very cozy cute little get away place. Very much so enjoyed our stay and the host was on top of always responding to any message fast and prompt."
United States
Renee H.
The price is AU$242
includes taxes & fees
16 Nov - 17 Nov
Riverside Romance/Luxury RV/Starry Skies & S'mores
A campfire with a picnic table nearby, surrounded by trees and a body of water.

5. 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$259
includes taxes & fees
1 Dec - 2 Dec
Romance Glamping | Pup Paradise | Near River | ADA
A view of a lake with surrounding greenery and a clear sky.

6. Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (22 reviews)
"Megan is a wonderful host, we enjoyed our stay!"
United States
Leeann
The price is AU$256
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage With a View in La Grange
A covered outdoor seating area with wooden furniture, string lights, and a view of the outdoors.

7. Indoor-Outdoor Escape, Screened Porch, Starlink

Indoor-Outdoor Escape, Screened Porch, Starlink
Paige
The price is AU$348
includes taxes & fees
16 Nov - 17 Nov
Indoor-Outdoor Escape, Screened Porch, Starlink
A wooden cabin with a porch, string lights, and a hanging chair.

8. Romantic Getaway, King Bed, Nature!

Romantic Getaway, King Bed, Nature!
Paige
The price is AU$361
includes taxes & fees
8 Dec - 9 Dec
Romantic Getaway, King Bed, Nature!
A living room with a sofa, a bed, a dining area, and a kitchen.

9. 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, (41 reviews)
"Extremely clean and very nicely furnished with unique artwork."
United States
Richard
The price is AU$331
includes taxes & fees
19 Nov - 20 Nov
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
A historic building with a symmetrical facade, arched windows, and a central entrance with a balcony.

10. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (118 reviews)
"I would definitely stay here again!"
United States
Anne Z.
The price is AU$297
includes taxes & fees
24 Nov - 25 Nov
Charming & Cozy Victorian in Quiet Residential Setting
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
10.0 out of 10, Exceptional, (12 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$247
includes taxes & fees
24 Nov - 25 Nov
Swiss Alp Texas Cabin
A wooden staircase with natural tree branches integrated into the structure, leading to a covered area.

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

The Hobbit's Nest Treehouse, A Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (239 reviews)
"Fun property, enjoyed our stay very much"
United States
Jessica H.
The price is AU$302
includes taxes & fees
8 Dec - 9 Dec
The Hobbit's Nest Treehouse, A Dog-friendly Treehouse in the Lost Pines Shire
A wooden playground with a slide, climbing area, and swings.

13. 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, (23 reviews)
"We enjoyed the quiet and no wi-fri.....the phone worked fine, don't like them either. Will stay there again if I ever get out to that area in Texas again. Thank you."
United States
James
The price is AU$427
includes taxes & fees
13 Dec - 14 Dec
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
A wooden cabin with a metal roof, a porch, and a fenced yard.

14. 10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture

10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture
Bastrop
The price is AU$212
includes taxes & fees
15 Nov - 16 Nov
10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture
A wooden cabin with a blue roof, surrounded by a wooden deck and metal railings, set in a forested area.

15. Elf's Aerie Treehouse - Outdoor Shower + Deck

Elf's Aerie Treehouse - Outdoor Shower + Deck
Paige
10.0 out of 10, Exceptional, (14 reviews)
"This was such an amazing stay! We will be back soon!"
United States
Isabel G.
The price is AU$302
includes taxes & fees
18 Nov - 19 Nov
Elf's Aerie Treehouse - Outdoor Shower + Deck
A spacious living room with a fireplace, a kitchen in the background, and a dining area with a table and chairs.

16. Walk to Lake + Stock Tank Pool + Fire Pit

Walk to Lake + Stock Tank Pool + Fire Pit
Bastrop
10.0 out of 10, Exceptional, (129 reviews)
"Awesome place to stay! Being from south Texas it sure was a change in scenery!"
United States
John P.
The price is AU$515
includes taxes & fees
16 Nov - 17 Nov
Walk to Lake + Stock Tank Pool + Fire Pit
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, (360 reviews)
"Comfy stay and parking made my trip easy!"
United States
Anonymous traveller
The price is AU$184
includes taxes & fees
22 Nov - 23 Nov
2 Queen Beds|Nsmk,Kitchen
A wooden deck with a railing, a bench, and a table with chairs.

18. Lost Pines Cottage - Fenced Yard + Dogs Stay Free

Lost Pines Cottage - Fenced Yard + Dogs Stay Free
Paige
10.0 out of 10, Exceptional, (405 reviews)
"Amazing location and just a great cabin. "
United States
Sean H.
The price is AU$300
includes taxes & fees
16 Nov - 17 Nov
Lost Pines Cottage - Fenced Yard + Dogs Stay Free
A wooden deck with a view of a forested area.

19. The Cactus House - Fenced Yard + Dogs Stay Free

The Cactus House - Fenced Yard + Dogs Stay Free
Paige
10.0 out of 10, Exceptional, (237 reviews)
"Fantastic little get away spot. Nice area to relax and within very close drive by range to either good BBQ or a distillery and brewery. Would definitely stay again."
United States
Josh S.
The Cactus House - Fenced Yard + Dogs Stay Free
A two-story house with a covered patio area, outdoor seating, and a dog.

20. Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (12 reviews)
"Fabulous stay, can’t wait to come back!"
United States
Karin C.
The price is AU$557
includes taxes & fees
9 Dec - 10 Dec
Round Top Refuge Guest 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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

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$127 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 Tejas Lake. In the wider area, you’ll find Bluff Creek Ranch and Texas Wendish Heritage Museum.

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.