Deale Beach Rentals By Owner

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

• Chesapeake Paradise House - Waterfront Vacation Rental Home on the Maryland Chesapeake Bay
• The 3 Bedroom Waterfront Cottage at Chesapeake Paradise near Annapolis MD
• Waterfront Spacious 5-bedroom vacation home with WiFi and AC in delightful Deale
• A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
• A WATERFRONT ESTATE ON THE CHESAPEAKE BAY, "THE DRIFTWOOD LODGE".
• 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
• Water Views- Boating Fishing -Annapolis-DC-Chesapeake Bay-Kayaking-Paddle Boards
• Calloway Drive Retreat | House in Shady Side
• *Chesapeake Bayside Bungalow*
• Renovated Waterfront Estate w/ Dock & Views!

There are many large, family-friendly vacation homes available in Deale Beach; however, here are the most popular family rentals listed on our site:

• 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
• Steps to Chesapeake Bay! Callaway Drive Retreat
• Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt
• Washington's Retreat

Yes, there are 43 self-catering vacation homes in Deale Beach that have hot tubs, swimming pools, & other amenities.

There are more than 43 luxury villas and vacation homes in or near Deale Beach. Filter by price to compare find the most expensive places to stay on Villasahara.

Yes, there are 43 pet friendly vacation homes and places to stays that are available in or near Deale Beach that you may consider.