Photo by Donny Campos

Search Holiday Rentals in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Winchester

Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Winchester you may be interested in

The Colonial Hotel
3.0 star property
8.6 out of 10, Excellent, (948)
"Beautiful hotel! Big room, very clean. Restaurant in the hotel. Would stay again."
The price is ₹11,768
₹13,145 total
includes taxes & fees
3 Nov - 4 Nov
The Colonial Hotel
The Covered Bridge Inn
2.5 star property
8.0 out of 10, Very good, (1011)
"Enjoyable stay"
The price is ₹8,828
₹9,711 total
includes taxes & fees
1 Nov - 2 Nov
The Covered Bridge Inn
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1010)
"Great place to stay while you are in town for a hike or bike ride. "
The price is ₹8,854
₹9,740 total
includes taxes & fees
6 Nov - 7 Nov
Colonial Motel And Spa
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.

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Rhododendron State Park, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Winchester. Make sure you have time to check out the forests and waterfront during your trip.

How many holiday rentals will I find in Winchester?

Expedia has 3 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Pisgah State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, Birch Point and Rhododendron State Park are other places worth a visit.

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 laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.