Deale, MD

Second Wind Consignments

Just a short stroll from Chesapeake Paradise, Second Wind Consignments offers a delightful mix of vintage treasures, home décor, and unique finds. This charming shop is a must-visit for guests seeking one-of-a-kind items to commemorate their stay.

Chesapeake Health & Fitness Club

Full service fitness club with yoga, arobics, childcare, daily memberships. About 3 minutes away (even though it's like we're in the country here!)

Chesapeake Drive

Drive 2 minutes to nearby Franklin Manor and follow to Chesapeake Dr. Nice 1/2 mile walk along residential bayfront. Or take right fork at Battee to walk around bayfront 'cloverleafs' at Cape Anne.

The Vineyards at Dodon

Elegant, eco-conscious, and rooted in history. Just 25 minutes from Chesapeake Paradise, The Vineyards at Dodon is a sustainably driven estate winery on a historic 555-acre farm. Enjoy intimate seated tastings and guided tours focused on regenerative farming and estate-grown wines in a calm, elegant setting.

Beer Farm at Homestead Gardens

Just 10 minutes from Chesapeake Paradise, The Beer Farm at Homestead Gardens offers a laid-back, dog-friendly taproom tucked inside one of the area's most beloved garden centers. Enjoy fresh, local craft brews surrounded by plants, patio lights, and seasonal charm.

Skipper's Pier Restaurant & Dock Bar

A beloved waterfront eatery in Deale, Maryland, Skipper’s Pier serves up fresh seafood, signature cocktails, and stunning Chesapeake Bay views—just a short drive from Chesapeake Paradise. Great evening sunsets, waterside casual dining and dock bar, fresh Maryland crabs/crabcakes/soup and other yummy food. Best when you can sit outside!

Thanksgiving Farm Winery

Historic charm meets small-batch elegance. Just 20 minutes from Chesapeake Paradise, Thanksgiving Farm & Winery in Harwood, MD, is a boutique vineyard offering estate-grown wines in a peaceful, countryside setting. Open seasonally for tastings, it’s a beautiful spot to sip, relax, and enjoy locally crafted wine.