Windsor 2024 Holidays

Photo by William E Berry Jr.
Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to €150 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Windsor

Hotel Coolidge
Hotel Coolidge
3 out of 5
39 South Main Street, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is €106 per night from 22 May to 23 May
€106
per night
22 May - 23 May
8/10 Very Good! (1,000 reviews)
"Historic hotel! Awesome corner king room. Yes, trains go by regularly but we had no problems with the "toot toooot" bc of the RR tracks nearby. Non-smoking so theres a cute court yard out back you can go if needed, parking is there too... very convenient to Dartmouth Hitchcock also. For the price ..."

Reviewed on 10 May 2024

Hotel Coolidge
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is €124 per night from 27 May to 28 May
€124
per night
27 May - 28 May
7.2/10 Good! (1,001 reviews)
Great place to stay. Highly recommended.
"This was a wonderful stay. Everyone, from front desk check in, to bartender, to Starbucks barista were warm, inviting, friendly, and helpful. The room was spotless. Appointed as advertised, and well cared for each day. I was pleasantly surprised and impressed overall."

Reviewed on 19 May 2024

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is €354 per night from 22 May to 23 May
€354
per night
22 May - 23 May
9.2/10 Wonderful! (441 reviews)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

Reviewed on 3 May 2024

Woodstock Inn & Resort
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?
Live it up in Windsor from as little as . We offer a wonderful selection of hotels, flights and rental cars to suit your budget. You can pick up even better deals when you add some activities or tours to your holiday package.
How do I get a cheap travel package to Windsor?
Our Windsor holiday packages promise plenty of savings for the savvy traveller. For the best deals, simply bundle your flights, hotels and extras (including activities) into an affordable package. But impressive bargains are only the start of your next unforgettable adventure. When you book with Expedia, you’ll have more than 550 air carriers and 1,000,000 hotels worldwide to select from. No matter your style or budget, there’s a holiday package with your name on it.
Where should I stay in Windsor?
With interesting attractions like Harpoon Brewery and Saint-Gaudens National Historic Site in this area, look for a hotel situated near them. Blow-Me-Down Bridge is another sight in Windsor that visitors flock to.
What are the top hotels in Windsor?
Get your escape off to a fantastic start by reserving a room at Windsor Mansion Inn. It’s one of most sought-after properties in Windsor. Another leading option is Snapdragon Inn.
How far in advance should I book my Windsor holiday?
Reserving your seat early with Expedia means one less thing to worry about. Most carriers advertise prices up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to Windsor will sometimes occur in the weeks leading up to departure.
What does an Expedia Windsor travel package include?
It comes down to what you want. If you’re travelling by yourself, you might decide to combine flights and hotels. Taking the whole crew to Windsor? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking a Windsor travel package?
Design deals that match your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You’ll save big dollars just by bundling your bookings. Whether you’re going on an adventure in the snow or getting some sun on a warm beach, your perfect holiday is only clicks away.
Can I choose my airline with a Windsor Expedia holiday package?
You certainly can. Expedia has access to more than 550 airline partners globally, so select the carrier that best suits your needs.
If I'm not able to travel, can I cancel my Windsor holiday package?
Yes, you can cancel your Windsor booking if your plans have been upended. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Popular places to visit

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