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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 HK$290
HK$548 total
includes taxes & fees
30 Sept - 1 Oct
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
9.2 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 HK$600
HK$1,209 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$826
HK$1,448 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$777
HK$1,229 total
includes taxes & fees
6 Oct - 7 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 HK$526
HK$1,281 total
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 HK$953
HK$1,541 total
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 HK$840
HK$1,796 total
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 HK$714
HK$1,495 total
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 HK$1,158
HK$2,757 total
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 HK$1,158
HK$2,757 total
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 HK$882
HK$1,300 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,098
HK$2,284 total
includes taxes & fees
6 Oct - 7 Oct
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 HK$1,236
HK$1,553 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,426
HK$3,506 total
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 HK$1,318
HK$1,646 total
includes taxes & fees
6 Oct - 7 Oct
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 HK$1,412
HK$1,654 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,109
HK$1,253 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,786
HK$3,893 total
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 HK$1,742
HK$2,882 total
includes taxes & fees
30 Sept - 1 Oct
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, (404 reviews)
"Amazing location and just a great cabin. "
United States
Sean H.
The price is HK$1,310
HK$1,637 total
includes taxes & fees
30 Sept - 1 Oct
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

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

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

10/10 Excellent
"Secluded family vacation for those who enjoy their privacy. Rental was too big to explore in such a short time. Hosts were friendly and eager to make stay as pleasant as possible."
Erik G. 2-night trip
Posted 12 hours ago
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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.