Windsor Holidays

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Windsor Holiday

Our pick of the best Windsor Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$252 per night from 15 July to 16 July
NZ$252
15 July - 16 July
includes taxes & fees
8.8/10 Excellent! (2,429 reviews)
"We absolutely love it there! Colleen at the front desk has been there a very long time she's sweet as can be! everyone is so nice and helpful, and the place is relaxing and clean we stay there quite often!"

Reviewed on 9 July 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$296 per night from 13 July to 14 July
NZ$296
13 July - 14 July
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, ..."

Reviewed on 9 July 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 9 Aug to 10 Aug
NZ$301
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Nice property good coffee"

Reviewed on 6 July 2026

Berkshire Mountain Lodge
See all 988 properties in Windsor
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.

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Windsor costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
You can generally find lower rates and greater availability in January, February and March. Take a look at our cheap Windsor holiday packages and you could score some great off-season discounts.
How many days is enough for Windsor?
The ideal length for your Windsor holiday depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Windsor package deals?
Use Expedia's filter tool to find some unbeatable Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Windsor package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and stays separately. Better still, you can customise your Windsor trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Windsor?
If you've got your Windsor holiday dates locked in, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Windsor?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Windsor.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to set aside for your trip to Windsor. Then, select a hotel that matches your budget, whether that's an economical option or a more upscale getaway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: After you've nailed down your travel dates and duration, book the right Windsor holiday package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.