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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester holiday rentals

Exterior

1. Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (81 reviews)
"Wonderful location, property was clean, very cozy"
United States
Billie P.
The price is HK$699
HK$1,064 total
includes taxes & fees
19 Aug - 20 Aug
Adorable Guest Cabin In The Woods
Interior

2. Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful property and the host was fast to respond to a minor A/C issue that came up."
United States
Micah P.
The price is HK$1,169
HK$1,693 total
includes taxes & fees
23 Aug - 24 Aug
Pinehaven Luxury Glamping
Property grounds

3. 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
16 Aug - 17 Aug
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
Property grounds

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, (15 reviews)
"We enjoyed our stay! This cottage is perfect for a getaway or planned layover between San Antonio and Austin. The vibe was great."
Canada
Paul
The price is HK$706
HK$1,155 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Cottage With a View in La Grange
Spa

5. 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
8.8 out of 10, Excellent, (5 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$667
HK$1,280 total
includes taxes & fees
12 Sept - 13 Sept
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Spa

6. 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, (6 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
The price is HK$968
HK$1,630 total
includes taxes & fees
17 Aug - 18 Aug
Dodo's Place on 22 acres outside of Smithville, TX
Interior

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (69 reviews)
"Great riverside spot. Very clean and comfortable."
United States
Wini H.
The price is HK$494
HK$1,246 total
includes taxes & fees
17 Aug - 18 Aug
Riverside Romance/Luxury RV/Starry Skies & S'mores
Exterior

8. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (113 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
The price is HK$953
HK$1,573 total
includes taxes & fees
27 Aug - 28 Aug
Charming & Cozy Victorian in Quiet Residential Setting
Property grounds

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

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4 reviews)
"We had an amazing time! We had everything we needed and more! It was nice and peaceful. A nice getaway from the city life. Being able to watch birds come up to the window was just awesome. Would love to stay again!"
United States
Cassie R.
The price is HK$526
HK$1,282 total
includes taxes & fees
16 Aug - 17 Aug
Romance Glamping | Pup Paradise | Near River | ADA
1 bedroom, WiFi, bed sheets

10. 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$883
HK$1,301 total
includes taxes & fees
16 Aug - 17 Aug
Swiss Alp Texas Cabin
Smart TV, DVD player, books, stereo

11. 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$1,859 total
includes taxes & fees
20 Aug - 21 Aug
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Children’s area

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$1,177
HK$2,499 total
includes taxes & fees
26 Aug - 27 Aug
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Exterior

13. 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$1,569
HK$2,833 total
includes taxes & fees
15 Aug - 16 Aug
Round Top Refuge Guest House
Terrace/patio

14. Steps away from the sweet LaGrange downtown square

Steps away from the sweet LaGrange downtown square
La Grange
9.4 out of 10, Exceptional, (11 reviews)
"A great place to stay. Very hospitable and enjoyed our stay!"
United States
William A.
The price is HK$1,499
HK$5,165 total
includes taxes & fees
15 Aug - 16 Aug
Steps away from the sweet LaGrange downtown square
Lobby

15. 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds|Nsmk,Kitchen
Giddings TX
10.0 out of 10, Exceptional, (51 reviews)
The price is HK$1,123
HK$1,269 total
includes taxes & fees
12 Sept - 13 Sept
2 Queen Beds|Nsmk,Kitchen
1 bedroom, desk, WiFi, bed sheets

16. Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.4 out of 10, Exceptional, (76 reviews)
"location is great and clean"
United States
Jeff H.
The price is HK$612
HK$1,775 total
includes taxes & fees
27 Aug - 28 Aug
Enchanting Casita, 5 minutes to Round Top!
Property grounds

17. 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, (237 reviews)
"Beautiful and peaceful little treehouse with all of the LOTR decor you would want. The owners thought of everything you could need and it was very comfortable."
United States
Amy P.
The price is HK$1,302
HK$1,652 total
includes taxes & fees
19 Aug - 20 Aug
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Living area

18. Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer

Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
Bastrop
10.0 out of 10, Exceptional, (2 reviews)
"really liked the area. the space was nice and cozy, very clean."
United States
sara
The price is HK$706
HK$1,280 total
includes taxes & fees
13 Sept - 14 Sept
Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
Terrace/patio

19. 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
9.8 out of 10, Exceptional, (10 reviews)
"We had a great time and everything we needed was available. "
United States
Jenna H.
The price is HK$1,236
HK$1,569 total
includes taxes & fees
18 Aug - 19 Aug
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Dining

20. Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
8.4 out of 10, Very good, (6 reviews)
"Amenities were plentiful."
United States
Karen G.
The price is HK$706
HK$1,897 total
includes taxes & fees
27 Aug - 28 Aug
Charming Cottage, 5 Minutes to Round Top!
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

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

10/10 Excellent
"I love hobbit holes and this place hit the spot! We had been staying in SPI and were heading back early to split the drive home into 2 days. The tree house was available for the one night we needed! Check in was easy, the space was clean, bed was comfortable, and we enjoyed the night playing cards. Lately when we've been trying to find places that are unique - very happy we found this place!"
Valerie Sean S. 1-night trip
Posted 3 days ago
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

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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Look no further and take a look at our great range of rental properties in Winchester!

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 The Old Fayette County Jail.

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.