Windsor Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Windsor

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 S$254 per night from 16 Dec to 17 Dec
S$254
includes taxes & fees
16 Dec - 17 Dec
7.2/10 Good! (1,001 reviews)
"We enjoyed our stay at the Killington Mountain Lodge and would definitely recommend it! The hot tub is awesome, the food/drinks served are good, the staff is super friendly, and the hotel itself was really nice. Super convenient location for skiing too."

Reviewed on 24 Nov,2024

Killington Mountain Lodge, Tapestry Collection by Hilton
Hampton Inn White River Junction
Hampton Inn White River Junction
2.5 out of 5
104 Ballardvale Dr, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is S$174 per night from 1 Dec to 2 Dec
S$174
includes taxes & fees
1 Dec - 2 Dec
8.4/10 Very Good! (1,001 reviews)
"No complaints."

Reviewed on 26 Nov,2024

Hampton Inn White River Junction
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$515 per night from 16 Dec to 17 Dec
S$515
includes taxes & fees
16 Dec - 17 Dec
9.2/10 Wonderful! (483 reviews)
"The overall experience was great."

Reviewed on 20 Nov,2024

Woodstock Inn & Resort
See all 2,469 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?
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.