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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winchester vacation rentals

Exterior

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (77 reviews)
"Wonderful location, property was clean, very cozy"
United States
Billie P.
The price is SAR 334
SAR 509 total
includes taxes & fees
27 Jun - 28 Jun
Adorable Guest Cabin In The Woods
Property grounds

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 SAR 402
SAR 621 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Cottage With a View in La Grange
Interior

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay. Very Peaceful. Everything was great. "
United States
Anonymous traveler
The price is SAR 559
SAR 799 total
includes taxes & fees
28 Jun - 29 Jun
Pinehaven Luxury Glamping
1 bedroom, WiFi, bed sheets

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (9 reviews)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
The price is SAR 422
SAR 622 total
includes taxes & fees
26 Jun - 27 Jun
Swiss Alp Texas Cabin
Spa

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, (5 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
The price is SAR 412
SAR 715 total
includes taxes & fees
7 Jul - 8 Jul
Dodo's Place on 22 acres outside of Smithville, TX
Exterior

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 SAR 591
SAR 1,164 total
includes taxes & fees
26 Jun - 27 Jun
Round Top Refuge Guest House
Living area

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
The price is SAR 284
SAR 571 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
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
Paige
10.0 out of 10, Exceptional, (22 reviews)
"This was the perfect getaway for our family to truly disconnect and unwind. The location was ideal for visiting the Sherwood Forest Faire, making our trip even more special. We loved getting to see the sheep, lambs, and chickens, which was such a fun experience for our 2-year-old. It was peaceful, family-friendly, and exactly what we were looking for. We would absolutely stay here again!"
United States
Jordyn D.
The price is SAR 563
SAR 1,192 total
includes taxes & fees
27 Jun - 28 Jun
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Living area

Round Top Refuge Main House

Round Top Refuge Main House
La Grange
10.0 out of 10, Exceptional, (4 reviews)
"Very Clean, Amazing Host, Wonderful location! Would definitely stay again!!"
United States
Colby W.
The price is SAR 676
SAR 1,264 total
includes taxes & fees
8 Jul - 9 Jul
Round Top Refuge Main House
Interior

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 reviews)
"This is our 3rd time staying with this host for the fall antique show and have had a pleasant stay each time. "
United States
Shawna M.
The price is SAR 507
SAR 799 total
includes taxes & fees
26 Jun - 27 Jun
Elm Grove Camper- Less than 3 miles from Round Top proper
Dining

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
8.4 out of 10, Very Good, (5 reviews)
"Amenities were plentiful."
United States
Karen G.
The price is SAR 375
SAR 942 total
includes taxes & fees
26 Jun - 27 Jun
Charming Cottage, 5 Minutes to Round Top!
Dining

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (60 reviews)
"Beautiful cottage, it was perfect for us!"
United States
Amy
The price is SAR 676
SAR 803 total
includes taxes & fees
28 Jun - 29 Jun
The White Magnolia Cottage
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..
Smithville
9.2 out of 10, Wonderful, (38 reviews)
"Had a great stay during the Christmas holidays to visit the Observatory. Good location."
United States
Albert C.
The price is SAR 402
SAR 882 total
includes taxes & fees
6 Jul - 7 Jul
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Spa

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
9.6 out of 10, Exceptional, (4 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 SAR 287
SAR 578 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
1 bedroom, desk, WiFi, bed sheets

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.4 out of 10, Exceptional, (76 reviews)
"Very cute! Easy access to town and an easy stay"
United States
Blah S.
The price is SAR 413
SAR 988 total
includes taxes & fees
29 Jun - 30 Jun
Enchanting Casita, 5 minutes to Round Top!
Property grounds

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, (235 reviews)
"It was more Magical than described, prepare to be amazed."
United States
Renee
The price is SAR 686
SAR 850 total
includes taxes & fees
28 Jun - 29 Jun
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Interior

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (66 reviews)
"Great riverside spot. Very clean and comfortable."
United States
Wini H.
The price is SAR 342
SAR 716 total
includes taxes & fees
19 Jul - 20 Jul
Riverside Romance/Luxury RV/Starry Skies & S'mores
Exterior

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (110 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
The price is SAR 557
SAR 875 total
includes taxes & fees
29 Jun - 30 Jun
Charming & Cozy Victorian in Quiet Residential Setting
Property grounds

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 SAR 435
SAR 834 total
includes taxes & fees
7 Jul - 8 Jul
Romance Glamping | Pup Paradise | Near River | ADA
Outdoor dining

Premium Lakefront Cabin #1: The Armadillo (Austin)

Premium Lakefront Cabin #1: The Armadillo (Austin)
Bastrop
The price is SAR 921
SAR 1,716 total
includes taxes & fees
8 Jul - 9 Jul
Premium Lakefront Cabin #1: The Armadillo (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

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping

10/10 Excellent
"Enjoyed the stay just what I needed to destress in some peace and quite"
Jennifer R. 3-night trip
Posted 12 hours ago
Pinehaven Luxury Glamping

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?

Waterfront Smithville River House: You might want to consider this vacation home rental near Winchester, which is located on the waterfront and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Boat Lake. 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.