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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor holiday rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,100 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is S$163
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Lobby

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,578 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
The price is S$137
includes taxes & fees
31 Aug - 1 Sept
Vacation Village in the Berkshires
Room

3. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is S$138
includes taxes & fees
8 Sept - 9 Sept
Huttopia Berkshires
Interior

4. 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$704
includes taxes & fees
29 Aug - 30 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"It is a safe place with friendly staff and clean accommodations; it is an excellent spot for traveling with children."
Jiye 2-night trip
Posted 3 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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.