Winchester Vacation Rentals

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winchester

Doran Bay Resort
Seasonal outdoor pool

Doran Bay Resort

2.5 star property
7.6 out of 10, Good, (20)
"We were happy with the cottage - pretty much what we expected. "
Doran Bay Resort
Abbott Road Suites
Private kitchen

Abbott Road Suites

3.5 star property
9.2 out of 10, Wonderful, (49)
"The suite that we were in was clean, cozy and comfortable. Our host Anne was very attentive and friendly. Her communication with us was excellent. If we’re in that area again, we will definitely say there again."
Abbott Road Suites
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Winchester you may be interested in

Terrace Green Bed & Breakfast
Premium bedding, blackout drapes, iron/ironing board, cribs/infant beds

Terrace Green Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (99)
"Annette has a beautiful property. We always feel extremely welcomed. Rooms are cozy and quiet."
The price is P4,846
P5,476 total
includes taxes & fees
Dec 6 - Dec 7
Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman
Front of property

Microtel by Wyndham Casselman

3.0 star property
9.0 out of 10, Wonderful, (775)
"Room was small with no fridge, which they probably mentioned, but it was an inconvenience. Very clean and in great condition otherwise. "
The price is P6,086
P6,877 total
includes taxes & fees
Nov 28 - Nov 29
Microtel by Wyndham Casselman
SureStay Hotel by Best Western Kemptville
Premium bedding, Select Comfort beds, desk, laptop workspace

SureStay Hotel by Best Western Kemptville

2.5 star property
8.0 out of 10, Very Good, (400)
"Nice room although small and the beds were hard. The staff and service were excellent. It was very quiet. Would definitely stay here again."
The price is P5,651
P6,386 total
includes taxes & fees
Nov 27 - Nov 28
SureStay Hotel by Best Western Kemptville
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 vacation rental in Winchester?

Yes, we offer vacation rentals near popular points of interest in Winchester, or you can go with a more remote option if you're looking for relaxation.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Calypso Water Park, or get outside and enjoy nature at Mountain Memorial Community Park. In the larger area, you’ll find Domaine du Cervin and Sandy Mountain Golf Course.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Winchester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.