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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Windsor vacation rentals

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Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,450 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is AED 457
AED 550 total
includes taxes & fees
19 Jul - 20 Jul
Vacation Village in the Berkshires
House (3 Bedrooms) | 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 AED 823
AED 2,035 total
includes taxes & fees
19 Jul - 20 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Family Bungalow

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.6 out of 10, Exceptional, (11 reviews)
"Healthy food too!"
United States
GEORGINA
The price is AED 558
AED 624 total
includes taxes & fees
19 Jul - 20 Jul
Huttopia 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Location is beautiful with scenic views. Families love the large pool and sand volleyball court. BBQ grills were in use daily. And the cooler evening lent itself to a lovely firepit. My stay was brief, but this looked like a great place for family reuinions."
Cathy 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, there are vacation rentals close to well known attractions in Windsor, or you can select a more secluded option if you'd like a relaxing place to stay. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental near Windsor offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Mount Greylock State Reservation Visitor Center. Susan B. Anthony Birthplace Museum and Skyline Trail are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Windsor. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.