Winchester Vacation Rentals

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Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winchester vacation rentals

Property grounds
Site 3 Private camp power @ site w/ Hot Showers & Potty In Community Bathhouse

Site 3 Private camp power @ site w/ Hot Showers & Potty In Community Bathhouse

Site 3 Private camp power @ site w/ Hot Showers & Potty In Community Bathhouse
1.0 star property
Smithville
The price is ￥2,108
￥7,839 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Site 3 Private camp power @ site w/ Hot Showers & Potty In Community Bathhouse
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
The price is ￥8,743
￥29,095 total
includes taxes & fees
Dec 31 - Jan 1, 2026
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
Exterior
Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (65)
"This was a great experience. The cabin was charming, clean, and easy to find. I really enjoyed staying in a quite, clean environment, watching the deer in the morning was a welcomed surprise, and it was easy to get to Round Top which was my weekend adventure. Thank you."
United States
Sherry
The price is ￥13,894
￥21,153 total
includes taxes & fees
Dec 29 - Dec 30
Adorable Guest Cabin In The Woods
Property grounds
Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (10)
"Perfecto para relajarte y pasar buen tiempo "
United States
Maria C.
The price is ￥14,051
￥22,981 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Cottage With a View in La Grange
Dining
Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
9.4 out of 10, Exceptional, (3)
"Amenities were plentiful."
United States
Karen G.
The price is ￥15,594
￥30,408 total
includes taxes & fees
Dec 26 - Dec 27
Charming Cottage, 5 Minutes to Round Top!
1 bedroom, WiFi, bed sheets
Swiss Alp Texas Cabin

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (8)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
The price is ￥17,543
￥25,847 total
includes taxes & fees
Dec 28 - Dec 29
Swiss Alp Texas Cabin
Exterior
Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top
Fayette County
8.8 out of 10, Excellent, (10)
"Great property, will stay again. "
United States
Jerry A.
The price is ￥15,594
￥39,141 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Lakefront Charm: Your Perfect Getaway in Round Top
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
The price is ￥7,244
￥19,902 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Terrys bungalow on the rivers edge with AC/Heat in a private campground!
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
The price is ￥9,356
￥25,433 total
includes taxes & fees
Dec 26 - Dec 27
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
Property grounds
Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4)
"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 ￥13,099
￥28,484 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Romance Glamping | Pup Paradise | Near River | ADA
Interior
Riverside Romance/Luxury RV/Starry Skies & S'mores

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (65)
"The area was near the river and i could see the stars at night. The sky both morning and night was beautiful. "
United States
veronica
The price is ￥13,411
￥28,840 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Riverside Romance/Luxury RV/Starry Skies & S'mores
Terrace/patio
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

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Smithville
8.0 out of 10, Very Good, (1)
"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 ￥11,929
￥24,028 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Smart TV, DVD player, books, stereo
Lost Pines Lake House near Bastrop State Park and Buescher State Park..

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, (29)
"We had very good and clean and comfortable accommodations. "
United States
Peter W.
The price is ￥13,894
￥27,600 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Interior
Elm Grove Camper- Less than 3 miles from Round Top proper

Elm Grove Camper- Less than 3 miles from Round Top proper

Elm Grove Camper- Less than 3 miles from Round Top proper
Round Top
9.6 out of 10, Exceptional, (27)
"The camper fit our needs perfectly! Quiet beautiful surroundings and close to all the activities that Round Top has to offer. We will definitely be back. Ashley the host was awesome!"
United States
Karen H.
The price is ￥21,052
￥33,340 total
includes taxes & fees
Dec 26 - Dec 27
Elm Grove Camper- Less than 3 miles from Round Top proper
Dining
The White Magnolia Cottage

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (48)
"It was beautiful! And so clean! Perfect for a girl’s weekend!!"
United States
Tisha K.
The price is ￥28,069
￥33,340 total
includes taxes & fees
Dec 28 - Dec 29
The White Magnolia Cottage
1 bedroom, desk, WiFi, bed sheets
Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.8 out of 10, Exceptional, (67)
"Absolutely love the uniqueness of the property. The chandelier is amazing! Fantastic stay with my hubby for my birthday! Thanks for making everything easy!"
United States
Jennifer W.
The price is ￥17,153
￥32,326 total
includes taxes & fees
Dec 26 - Dec 27
Enchanting Casita, 5 minutes to Round Top!
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.
The price is ￥24,589
￥47,765 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Round Top Refuge Guest House
Children's area
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

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
9.8 out of 10, Exceptional, (19)
"The cabin was beautiful and very clean. The owner even left some muffins. The property is nicely maintained for a hike. Check in is easy and the owner is available if needed. I will stay there again next year. Highly recommend."
United States
Pam M.
The price is ￥23,391
￥49,511 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Interior
Pinehaven Luxury Glamping

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (51)
"Great location, quiet stay. "
United States
Brandon R.
The price is ￥26,354
￥36,325 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Pinehaven Luxury Glamping
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, (5)
The price is ￥27,477
￥32,560 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Modern Retreat in the Pine Forest of Bastrop
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

River Valley Motor Inn

River Valley Motor Inn

10/10 Excellent
"Room very clean! Plenty towels Front desk person so nice! "
Cathy 1-night trip
Posted 2 days ago
River Valley Motor Inn

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 vacation rental in Winchester?

Yes, we give you a choice of vacation rentals near popular sights in Winchester, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Winchester?

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire: You might want to consider this vacation home rental near Winchester, which is located in a rural location and has a fireplace, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

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 larger area, you’ll find Bluff Creek Ranch and Buescher State Park.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties where you can stay for several days or longer in Winchester. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.