Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by mike dobias

Top hotels in Windsor

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is 3.104.363 ₫ per night from 24 Jun to 25 Jun
3.104.363 ₫
3.414.800 ₫ total
24 Jun - 25 Jun
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Great staff, good location a short walk from the historic center. A bit expensive."

Reviewed on 21 Jun 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is 11.210.199 ₫ per night from 6 Jul to 7 Jul
11.210.199 ₫
13.480.983 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on 20 Jun 2025

Woodstock Inn & Resort
Super 8 by Wyndham White River Junction
Super 8 by Wyndham White River Junction
2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is 2.198.924 ₫ per night from 30 Jun to 1 Jul
2.198.924 ₫
2.418.818 ₫ total
30 Jun - 1 Jul
includes taxes & fees
6.2/10 (1,005 reviews)
"The location is very easy to access close enough to restaurants and other necessities nearby in White River junction. The staff was excellent very friendly and helpful. The building itself needs some maintenance in terms of structural and cosmetic attention. The room was clean the bed was comfortable ..."

Reviewed on 17 Jun 2025

Super 8 by Wyndham White River Junction
See all 2,596 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?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday to Windsor costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
To score cheap Windsor holiday packages, plan your trip outside of peak times like public holidays and major events. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Windsor?
With a well-organised schedule, you can easily visit the main Windsor sights in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your Windsor holiday for longer.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an amazing escape. Begin your Windsor holiday on a high note by visiting major attractions like South Congregational Church.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor break by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Windsor?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor holiday.
How to plan a trip to Windsor?

  1. Pick your travel dates: The things you'd like to do in Windsor and your preferred season can help you decide when to get away.
  2. Budget wisely: Besides the price of your stay, you should factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Windsor.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised Windsor holiday package.

Popular places to visit

Harpoon Brewery

You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forests or discover the area's mountain views.

Harpoon Brewery

American Precision Museum

You can spend time exploring the galleries in American Precision Museum during your travels in Windsor. Wander the riverfront in this quaint area.

American Precision Museum

Brownsville Trail

You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area or seek out the ski slopes.

Brownsville Trail