Windsor Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Windsor holiday rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,333 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is S$162
includes taxes & fees
3 May - 4 May
Vacation Village in the Berkshires
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is S$705
includes taxes & fees
14 Apr - 15 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is S$694
includes taxes & fees
14 Apr - 15 Apr
12-acre Vacation Rental 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

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good
"Parking was great. Check-in and Check-out great. Very clean, comfortable bed, great location for me. The one issue for me was that the keys did not work every time. I asked to have them fixed and the lovely staff did so each time, but the keys still gave me trouble. I was worried that I could not get back into my room. There might be an issue with the censor in the room. I would stay there again. It is a great value. "
Susan 3-night trip
Posted 3 hours ago
Red Roof Inn PLUS+ South Deerfield – Amherst

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. Susan B. Anthony Birthplace Museum and Mount Greylock State Reservation Visitor Center 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.