Virginia Beach Winter Rentals & Holiday Homes

There are a lot of options in Virginia Beach. If you plan on staying in the Virginia Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Virginia Beach:

• The Historic Cavalier Hotel and Beach Club, Autograph Collection
• Embassy Suites by Hilton Virginia Beach Oceanfront Resort
• The Historic Cavalier Hotel and Beach Club Autograph Collection
• Pool House Getaway - Hot Tub, Sauna, Steam Shower & a 50' Pool
• Available Aug 23-30
• Ocean Sands Resort with a nice Oceanfront Balcony
• Ocean Sands Resort with a nice Oceanfront Balcony
• Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
• Four Sails Resort 1BR 1BA Double Oceanfront Balcony & DOUBLE Wide Jetted Tub
• Oceanfront in Virginia Beach with balcony overlooking the beach

The average cost for winter rentals in Virginia Beach is $540 per night. Unpluggedweekend has a wide list of great winter places to stay near Virginia Beach that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Virginia Beach that allow you to bring your pet or dog:

• Reunion Paradise! amazing property for reunions and traveling teams sports
• Catch N Relax
• Barclay Cottage
• Beachfront Luxury Home,SALT WATER, POOL- Heating is an Option &SPA,Pet Friendly

See all pet-friendly vacation rentals in Virginia Beach on Unpluggedweekend

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Virginia Beach to find what works for you.

As of 2026, the data from Unpluggedweekend shows that there are over 96 private swimming pools or indoor pools accommodations near Virginia Beach along with other great amenities.