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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday rentals

A modern two-story house with a stone facade, a large garage, and a well-maintained lawn.

1. The best stay in Bastrop Texas

The best stay in Bastrop Texas
3.0 star property
Bastrop
The best stay in Bastrop Texas
A single-story house with a front porch, a red door, and a small staircase leading to the entrance.

2. Boutique Retreat Minutes From Round Top!

Boutique Retreat Minutes From Round Top!
3.0 star property
Fayetteville
The price is 11.824.992 ₫
17.578.525 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Boutique Retreat Minutes From 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 Oak Motel

The Oak Motel

10/10 Excellent
"Cutest little motel within walking steps to downtown square and coffee shops and cafes and antique stores . Room had all essentials like fridge, microwave and coffee maker. Nice outside sitting area. Highly recommend."
Desiree 2-night trip
Posted 2 days ago
The Oak Motel

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 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.