House holiday rentals in Deale

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Cook wonderful meals in our well-equipped kitchen. Or try some our local restaurants. Great place for families or multi family groups.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Quaint in the Heart of Annapolis

Quaint 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views & wildlife. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit, and hot tub on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Waterfront w/ Private Pier, 35 Mins to Annapolis

Shady Side is a quaint town located 35 min. from Annapolis and an hour from Washington, D.C or Baltimore. This waterfront home is perfect for families or small groups looking for a relaxing getaway on the Chesapeake Bay. Enjoy the wrap-around screened porch, private pier with ladder for swimming, large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 minutes away in Parish Creek. Listed for 8 people max. Contact us for approval of 1-2 more.

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.