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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Windsor holiday rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,259 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is Rp1.388.421
Rp1.954.974 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
Indoor pool

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is Rp1.453.306
Rp1.821.780 total
includes taxes & fees
9 Nov - 10 Nov
Vacation Village in the Berkshires
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 Windsor Hotel Reviews

Exterior
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield

8/10 Good

Laundrette being free really useful. Coffee in main lobby superb quality. Only a few minutes from Market 32 for good food and provisions. A couple of downsides - check-in staff were not particularly friendly and there is a high deposit. Rooms are suites so loads of space.
United Kingdom
James
Reviewed October 6, 2026
Berkshire Mountain Lodge

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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. Windsor is known for its restaurants and shopping.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Wahconah Falls State Park. Mount Greylock State Reservation Visitor Center and Pontoosuc Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.