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Top Holiday Rentals in Windsor

Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is £614
includes taxes & fees
27 Jun - 28 Jun
Western Mass Getaway-Airhockey-Hot tub-Firepit

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (1)
"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "
The price is £255
includes taxes & fees
6 Jul - 7 Jul
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is £391
includes taxes & fees
8 Jul - 9 Jul
2.5mi from the lake! Fire pit, arcade, yard games!

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is £631
includes taxes & fees
6 Jul - 7 Jul
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Tranquil Retreat 6-BR Total in the Berkshires

The price is £1,091
includes taxes & fees
7 Jul - 8 Jul
Tranquil Retreat 6-BR Total in the Berkshires

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is £283
includes taxes & fees
9 Jul - 10 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is £117
includes taxes & fees
30 Jun - 1 Jul
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is £553
includes taxes & fees
2 Jul - 3 Jul
Spacious 5-bedroom house in charming Lee with WiFi

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is £334
includes taxes & fees
30 Jun - 1 Jul
North Getaway Cottage

New Home - Heart of Williamstown 183

10.0 out of 10, Exceptional, (1)
"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."
The price is £943
includes taxes & fees
2 Jul - 3 Jul
New Home - Heart of Williamstown 183

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (69)
"We had a wonderful stay, thank you! "
The price is £409
includes taxes & fees
29 Jun - 30 Jun
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is £360
includes taxes & fees
26 Jun - 27 Jun
Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is £826
includes taxes & fees
8 Jul - 9 Jul
Hancock Village Inn at Jiminy Peak

Enchanting Cottage, Come Enjoy Nature!

10.0 out of 10, Exceptional, (1)
"If you want TV, this isnt for you, but if you want a quiet place to check away and relax it fits the bill wonderfully"
The price is £767
includes taxes & fees
5 Jul - 6 Jul
Enchanting Cottage, Come Enjoy Nature!

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is £352
includes taxes & fees
30 Jun - 1 Jul
NEW RENO Historic Creamery in Berkshires w/hot tub
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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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 are some of the best holiday rentals that Windsor has to offer?

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Windsor is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

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 Swift River 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.