Search Vacation Homes in Winchester

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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Winchester vacation homes

Dining
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake

2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake

2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
2.0 star property
Bastrop
10.0 out of 10, Exceptional, (2)
"Amazing host ! Did a great job making the stay feel like home . Beautiful place and very clean ! Host was outstanding great communication awesome amenities. 10/10 recommend will definitely continue booking here for future stays ! "
United States
Alex
$162 nightly
The price is $170
Dec 16 - Dec 17
Total with taxes and fees
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
Property grounds
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

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

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (215)
"Great stay at the Cactus House. Highly recommend if you need a little oasis in Paige Texas! "
United States
Georgia Y.
$206 nightly
The price is $230
Dec 11 - Dec 12
Total with taxes and fees
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Private kitchen
Modern Retreat in the Pine Forest of Bastrop

Modern Retreat in the Pine Forest of Bastrop

Modern Retreat in the Pine Forest of Bastrop
2.0 star property
Bastrop
10.0 out of 10, Exceptional, (4)
"We had a great stay, house was immaculate, quiet neighborhood, loved it"
United States
Faye B.
$153 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Modern Retreat in the Pine Forest of Bastrop
Terrace/patio
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

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (387)
"We enjoyed our stay."
Germany
Eva C.
$183 nightly
The price is $204
Dec 14 - Dec 15
Total with taxes and fees
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Exterior
Round Top Refuge Guest House

Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (5)
"Great place to stay! "
United States
Natalie S.
$291 nightly
The price is $306
Dec 11 - Dec 12
Total with taxes and fees
Round Top Refuge Guest House
Exterior
Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (102)
"Such a beauty of a house! Highly recommend staying here if you are ever in Bastrop for the night! "
United States
Jim C.
$222 nightly
The price is $233
Dec 14 - Dec 15
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
1 bedroom, iron/ironing board, WiFi, bed sheets
PineyWoods House Forest Retreat

PineyWoods House Forest Retreat

PineyWoods House Forest Retreat
Bastrop County
10.0 out of 10, Exceptional, (12)
"Had the best time deer are.present and the cabin is gorgeous! Host was amazing"
United States
Stephanie M.
$186 nightly
The price is $207
Jan 6 - Jan 7, 2026
Total with taxes and fees
PineyWoods House Forest Retreat
1 bedroom, free WiFi
Terrys bungalow on the rivers edge with AC/Heat in a private campground!

Terrys bungalow on the rivers edge with AC/Heat in a private campground!

Terrys bungalow on the rivers edge with AC/Heat in a private campground!
2.0 star property
Smithville
Terrys bungalow on the rivers edge with AC/Heat in a private campground!
Smart TV
The Top @ Round Top + Escape to the country!

The Top @ Round Top + Escape to the country!

The Top @ Round Top + Escape to the country!
Round Top
10.0 out of 10, Exceptional, (28)
"We had a great time at this property! It is so close to town, very spacious and the check in process was so easy! We will definitely be back."
United States
Madison M.
$469 nightly
The price is $494
Dec 11 - Dec 12
Total with taxes and fees
The Top @ Round Top + Escape to the country!
Interior
Spacious country retreat with modern amenities KING SIZE BED & family friendly

Spacious country retreat with modern amenities KING SIZE BED & family friendly

Spacious country retreat with modern amenities KING SIZE BED & family friendly
Bastrop
8.4 out of 10, Very Good, (5)
"It was clean and spacious."
United States
Sadia E.
$291 nightly
The price is $307
Dec 14 - Dec 15
Total with taxes and fees
Spacious country retreat with modern amenities KING SIZE BED & family friendly
Terrace/patio
The Addi - Farmstead

The Addi - Farmstead

The Addi - Farmstead
Round Top
10.0 out of 10, Exceptional, (1)
"VRBO accidentally has this listed as a 2 bedroom rental. It is actually a 1 bedroom. The property manager was wonderful to work with and we worked out a solution. The rental was very clean and organized, modern finishes, amazing shower, towels and robes. We absolutely loved our stay here. "
United States
Debbie S.
$354 nightly
The price is $372
Dec 11 - Dec 12
Total with taxes and fees
The Addi - Farmstead
Smart TV
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake

Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake

Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
2.0 star property
Bastrop
$155 nightly
The price is $163
Dec 22 - Dec 23
Total with taxes and fees
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
TV
The Ramona House w/ Cowboy Pool! Walk to Downtown!

The Ramona House w/ Cowboy Pool! Walk to Downtown!

The Ramona House w/ Cowboy Pool! Walk to Downtown!
Downtown Smithville
10.0 out of 10, Exceptional, (10)
"We had a great stay at the house and enjoyed our visit to Smithville. We rented to attend Round Top and loved our stay here! It was beautiful! We would definitely stay here again!"
United States
Jeanine K.
$536 nightly
The price is $536
Dec 15 - Dec 16
Total with taxes and fees
The Ramona House w/ Cowboy Pool! Walk to Downtown!
Smart TV, books
Spacious home 2 minutes from downtown (Pet-Friendly!)

Spacious home 2 minutes from downtown (Pet-Friendly!)

Spacious home 2 minutes from downtown (Pet-Friendly!)
Smithville
9.6 out of 10, Exceptional, (14)
"This home was clean, comfortable and perfectly located in the heart of Smithville. We will be coming back!"
United States
Natalia M.
$302 nightly
The price is $338
Dec 14 - Dec 15
Total with taxes and fees
Spacious home 2 minutes from downtown (Pet-Friendly!)
Terrace/patio
The Hideaway ÖÖD Mirror House (Austin)

The Hideaway ÖÖD Mirror House (Austin)

The Hideaway ÖÖD Mirror House (Austin)
Bastrop
10.0 out of 10, Exceptional, (2)
"This property is so unique. The large glass windows allowed for some great wildlife views. I loved the plunge pool and the park was nice too. Check in and communication was excellent!"
United States
Stacey S.
$396 nightly
The price is $429
Dec 14 - Dec 15
Total with taxes and fees
The Hideaway ÖÖD Mirror House (Austin)
Interior
A Sanctuary of Stories!

A Sanctuary of Stories!

A Sanctuary of Stories!
Round Top
9.0 out of 10, Wonderful, (6)
"Beautiful property! Can’t wait to come back."
United States
Dario B.
$1,112 nightly
The price is $1,171
Dec 13 - Dec 14
Total with taxes and fees
A Sanctuary of Stories!
Fridge, microwave, oven, dishwasher
Designory Round Top home, scenic views & pond!

Designory Round Top home, scenic views & pond!

Designory Round Top home, scenic views & pond!
Round Top
10.0 out of 10, Exceptional, (7)
"We came to Warrenton for a concert at the Round Top Festival Hill. This home is perfect for 2 couples, with each room allowing privacy. The home was clean and well-stocked. The decor is lovely! Would stay here again! "
United States
Stephanie A.
$469 nightly
The price is $481
Jan 6 - Jan 7, 2026
Total with taxes and fees
Designory Round Top home, scenic views & pond!
TV, fireplace
Swim, Grill, Chill, Repeat - Perfect for Families

Swim, Grill, Chill, Repeat - Perfect for Families

Swim, Grill, Chill, Repeat - Perfect for Families
Carmine
10.0 out of 10, Exceptional, (6)
"We absolutely loved our stay at this property and our group is already thinking about how and when we can come back. The house was perfect for our girls weekend—lots of space to hang out together, a fabulous pool, and everyone got their own bed. Hostie also went above and beyond to make sure our stay was enjoyable. I highly recommend staying at a Hostie property for your next getaway!"
United States
Macie H.
$1,184 nightly
The price is $1,243
Dec 11 - Dec 12
Total with taxes and fees
Swim, Grill, Chill, Repeat - Perfect for Families
Dining
Luxurious Stargazer Dome Retreat in Stunning Nature

Luxurious Stargazer Dome Retreat in Stunning Nature

Luxurious Stargazer Dome Retreat in Stunning Nature
Smithville
$565 nightly
The price is $595
Dec 15 - Dec 16
Total with taxes and fees
Luxurious Stargazer Dome Retreat in Stunning Nature
Terrace/patio
The Bloom ÖÖD Mirror House (Austin)

The Bloom ÖÖD Mirror House (Austin)

The Bloom ÖÖD Mirror House (Austin)
Bastrop
$396 nightly
The price is $429
Dec 14 - Dec 15
Total with taxes and fees
The Bloom ÖÖD Mirror House (Austin)
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

Days Inn by Wyndham Bastrop

Days Inn by Wyndham Bastrop

10/10 Excellent
"Usual basic amenities, excellent staff."
Eugene 2-night trip
Posted 6 days ago
Days Inn by Wyndham Bastrop

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
793
Accommodation
125 Vacation Homes
Lowest Price
$161
Highest Price
$1,243

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