Windsor Vacations from $148

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Your Windsor Vacation

The exciting city of Windsor is calling your name. Delve into everything from its highlights to its hidden gems with a Windsor vacation package that's custom made for you. During your trip to Windsor, take all the time you need for sightseeing. A perfect place to start exploring is Lake Prince. That dream Windsor vacation is clicks away. Browse accommodations, flights and more on Expedia for a getaway that's tailored to suit your style.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
LABH INC

LABH INC

2.5 out of 5
Price was $215, price is now $148 per person
$148
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
4/10 (7 reviews)

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $560, price is now $371 per person
$371
per person
Sep 13 - Sep 17
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9.2/10 Wonderful! (1,938 reviews)

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $459, price is now $327 per person
$327
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,559 reviews)
Really liked the location 2 blocks away from the beach and the board walk. Lots of restaurants around and the free parking was very useful. The staff was very pleasant and had a great experience from the front desk staff (Queeny) to the maintenance team (Derron). Derron was so friendly and thoughtful that he made our experience truly memorable.

Reviewed on Jul 26, 2026

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $975, price is now $703 per person
$703
per person
Oct 13 - Oct 20
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,503 reviews)
The elevator was broken and also the pool was COLD so was the beach is what i disliked

Reviewed on Jul 26, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $771, price is now $582 per person
$582
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,337 reviews)
Staff was very friendly and helpful. Beach view was excellent! Common areas were very clean and well kept. Room was smaller than expected. Once the fold out couch/bed was open there was limited space to move from bedroom to the bathroom. Internet was disappointing, couldn't access on balcony and limited in room. Parking spaces were very tight but at least there was an available space. Location to activities and food was terrific. We were able to walk to everything.

Reviewed on Jul 25, 2026

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Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)
This 18th-century tavern showcases original colonial paneling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.
See properties

Windsor Hotel Deals

Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $110 total per night from Aug 2 to Aug 3
$110 total
Aug 2 - Aug 3
Total with taxes and fees
7/10 Good! (1,028 reviews)
"The hotel is centrally located and a lovely property as it’s quite grand and picturesque. However, the property itself is dated. It’s clear that they’ve done some renovations to the space but it smells old. When you walk in to the lobby the scent of mildew is faint but not to a keen nose. Our rooms ..."

Reviewed on Jul 26, 2026

Wyndham Garden Norfolk Downtown
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Fully refundable
$94 nightly
The price is $109 total per night from Aug 3 to Aug 4
$109 total
Aug 3 - Aug 4
Total with taxes and fees
8.8/10 Excellent! (1,070 reviews)
"Room was clean and bed was extremely comfortable. The hotel was busy while we were there but our room was very quiet (and we were close to the elevator too!). It was a great place to stay for a 2 night trip."

Reviewed on Jul 26, 2026

Comfort Suites Airport
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $285 total per night from Jul 28 to Jul 29
$285 total
Jul 28 - Jul 29
Total with taxes and fees
Kingsmill Resort
See all 696 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Newport News - Williamsburg Intl. Airport (PHF)
Population
2,700
Top Sights
Riddicks Folly House Museum, Lake Prince and Suffolk Seaboard Station Railroad Museum

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $148 on Expedia, you'll be thrilled with how little a vacation to Windsor costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
If you're hoping to book a cheap Windsor vacation package, consider visiting in December, January and February. You'll usually find lower prices on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Windsor?
The ideal duration for your Windsor vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the leading attractions and discover some hidden spots along the way.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Windsor package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Windsor trip.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Jet off on your perfect escape to Windsor with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up bargains while they last.

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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.