Winchester Holiday Rentals

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Holiday Rentals in Winchester

Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (32)
"Very nice management "
The price is S$194
includes taxes & fees
3 Dec - 4 Dec
Family Farmhouse Inn
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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Other types of properties in Winchester you may be interested in

La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.2 out of 10, Wonderful, (1718)
"This property is older and does need some tlc. But everything was wonderfully taken care of and it was so clean. I've never seen a place be as clean as this. There was constantly someone doing work"
The price is S$139
includes taxes & fees
15 Dec - 16 Dec
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1049)
"Great efficient modern property. Well designed. I would stay here again. "
The price is S$110
includes taxes & fees
8 Dec - 9 Dec
Microtel Inn & Suites by Wyndham Winchester
Red Roof Inn Winchester, VA
2.0 star property
7.4 out of 10, Good, (1004)
"As described "
The price is S$88
includes taxes & fees
22 Dec - 23 Dec
Red Roof Inn Winchester, VA
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

How many holiday rentals will I find in Winchester?

Choose from 21 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Museum of the Shenandoah Valley and Bright Box Theater. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

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 extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.