Windsor Holiday 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

Holiday Rentals in Windsor

Rustic Waterfront Cottage w/ Fire Pit & Kayaks
Fireplace

Rustic Waterfront Cottage w/ Fire Pit & Kayaks

2.5 star property
Rustic Waterfront Cottage w/ Fire Pit & Kayaks
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 Windsor
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 Windsor you may be interested in

Courtyard by Marriott Keene Downtown
Hypo-allergenic bedding, in-room safe, desk, laptop workspace

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1002)
"Well appointments room, very spacious and quiet. Fan I bathroom did not work "
The price is S$153
includes taxes & fees
2 Jan - 3 Jan,2025
Courtyard by Marriott Keene Downtown
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (260)
"Exceeded my expectations."
The price is S$196
includes taxes & fees
18 Dec - 19 Dec
Hampton Inn & Suites Keene
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (968)
"Staff was very supportive and polite. We appreciated the breakfast, the fridge and microwave which other motels we stayed at on this trip did not include. "
The price is S$115
includes taxes & fees
8 Dec - 9 Dec
Days Inn by Wyndham Keene NH
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

Black Friday: Members save 30%+

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

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Windsor?

Expedia has 5 holiday rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Quilted Threads, or get out into nature at a spot like Contoocook River. In the wider area, you’ll find Franklin Pierce Homestead and Pats Peak.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.