Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
per person
Aug 8 - Aug 12
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Norfolk (ORF)
8.2/10 Very Good! (1,370 reviews)
very convenient to the downtown. loved that doors were secured at all hours

Reviewed on Jul. 7, 2025

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 5 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Norfolk (ORF)
9.4/10 Exceptional! (10 reviews)
Rooms are very nice. Like a studio apartment setup. Cozy and spacious. Beach is a very short walk away. Have plenty of restaurants, shops, and attractions nearby. Definitely going again in the future.

Reviewed on Jun. 5, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 5 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Norfolk (ORF)
9/10 Wonderful! (1,781 reviews)
Room was one of the best that I have ever stayed in. Lots of room, kitchette, nice bathroom. Just a few minutes walk and you are on the beach. Very nice gazebo for looking over the ocean. Would return and stay again in a heartbeat.

Reviewed on Jul. 7, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 5 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Norfolk (ORF)
8.6/10 Excellent! (1,005 reviews)
Very nice and convenient place to stay.

Reviewed on Jul. 5, 2025

Sleeps 28 Beachfront w/ Pool, Hot Tub, Game Room Atlantic Watch by Avantstay

Sleeps 28 Beachfront w/ Pool, Hot Tub, Game Room Atlantic Watch by Avantstay

3 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 5 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Norfolk (ORF)
No reviews

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Windsor Hotel Deals

The Landing at Hampton Marina, Tapestry Collection by Hilton
The Landing at Hampton Marina, Tapestry Collection by Hilton
3.5 out of 5
700 Settlers Landing Rd., Hampton, VA
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 3 to Aug 4
CA $155
CA $181 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"The food and the views were the best part ! Love the menu and the privacy will be coming back"

Reviewed on Jul. 2, 2025

The Landing at Hampton Marina, Tapestry Collection by Hilton
Norfolk Waterside Marriott
Norfolk Waterside Marriott
3.5 out of 5
235 E Main St, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Aug 4 to Aug 5
CA $195
CA $229 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Beautiful views and centrally located. Breakfast was delicious. The staff was very friendly."

Reviewed on Jul. 4, 2025

Norfolk Waterside Marriott
Comfort Inn Newport News - Hampton I-64
Comfort Inn Newport News - Hampton I-64
2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Jul 20 to Jul 21
CA $114
CA $133 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"Hotel was clean. Staff was friendly. The question about environmental I didn’t see any recycling containers"

Reviewed on Jul. 4, 2025

Comfort Inn Newport News - Hampton I-64
See all 689 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $834 on Expedia, you'll be thrilled with how little a vacation to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Windsor vacation packages and you could get some great off-season deals.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily visit the most popular Windsor sights in a handful of days. But if you want to venture off the beaten track or go on day trips, consider booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's handy filters to find some tempting Windsor package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Windsor package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Windsor trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor vacation dates finalized, book as early as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Windsor?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Windsor.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to set aside for your trip to Windsor. Then, pick a property that suits your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Windsor vacation package that brings all your bookings together.

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