Windsor Woods Vacation Packages

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Top Holiday Package Deals in Windsor Woods

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

Boardwalk Resort and Villas

Northeast Virginia Beach

CA $1,148

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.8/10 Excellent! (1,024 reviews)

It was a Pleasant stay.

Reviewed on Sep 4, 2026

The Colony at Virginia Beach

Northeast Virginia Beach

CA $1,404

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

9.6/10 Exceptional! (42 reviews)

The Sitio

Northeast Virginia Beach

CA $1,760

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

9.6/10 Exceptional! (61 reviews)

Very very nice place my wife and i really enjoyed ourselves. We just wish that the wave pools were more excessible for the people not just for the surfers. It's 2 big wave pools and plenty of room to enjoy the pool as well

Reviewed on Sep 3, 2026

4BR Waterfront Penthouse Pool Views

Sandbridge

CA $2,629

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

No reviews

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

CA $1,189

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.2/10 Very good! (1,380 reviews)

I go every year for my mini vacation! I love it here!

Reviewed on Sep 2, 2026

Where to stay in Windsor Woods

Find the best Windsor Woods areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Woods

A night scene with a tower and a prominent tree against a starry sky.

Northeast Virginia Beach

5 out of top 10 points of interest in this area

While visiting Northeast Virginia Beach, you might make a stop by sights like First Landing State Park and Neptune Statue.

A sandy beach with gentle waves, a clear blue sky, and houses along the shore.

Sandbridge

Somewhat remote and less crowded than the main resort strip, Sandbridge offers a 4.5-mile stretch of oceanfront with lifeguard-protected waters. Nearby, find Little Island Park and easy access to shopping and dining centers at Red Mill and Courthouse.

A sunset over the ocean with tall grasses in the foreground.

Dam Neck

1 out of top 10 points of interest in this area

If you're spending some time in Dam Neck, Sandbridge Beach and Croatan Beach are top sights worth seeing.

Northwest

While visiting Northwest, you might make a stop by sights like Sandler Center for the Performing Arts and Norfolk Premium Outlets.

A nighttime cityscape with illuminated buildings and a bridge with underlit arches.

Virginia Beach Town Center

One reason travelers love spending time in Virginia Beach Town Center is the stunning beaches, and Sandler Center for the Performing Arts is a top place to visit.

Windsor Woods Hotel Deals

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA

Fully refundableReserve now, pay when you stay

CA $120

CA $151 total

Oct 4 - Oct 5

includes taxes & fees

Holiday Inn & Suites Virginia Beach North Beach by IHG

3900 Atlantic Avenue Virginia Beach VA

Fully refundable

CA $186

CA $217 total

Oct 1 - Oct 2

includes taxes & fees

8/10 Very good! (1,521 reviews)

"Nice stay with my family, staff was pleasent. Drove for six hours and staff gave us two hours before are our check in."

Reviewed on Sep 3, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Fully refundable

CA $104

CA $123 total

Oct 4 - Oct 5

includes taxes & fees

See all 2,939 properties in Windsor Woods

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.