Holiday rentals with a hot tub in Calvert County

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

Waterfront, Dog-friendly, Hot Tub, Peleton

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 winter dates**

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

Private, Lakefront Oasis- Lavinia by the Lake

This home is the embodiment of true Southern Maryland waterfront living. It is the best location for Rockfish, crabbing and oystering!The house is fully gated so you will always have peace of mind while your kids and pets wander around. This 5 bedroom, 3 bathroom stunner with a full walk out basement is perfect for the larger water loving family who loves to entertain. The outdoor living space hits all the marks: upper and lower deck, umbrellas throughout, a Gazebo bar, Hot Tub and more.

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

Blue Heron Retreat-Water views-hot tub-dock-kayaks

This peaceful open concept home is nestled among the trees, with water views and nature from every window as well as from the two-level deck which offers plenty of seating for relaxing or dining with friends and family. Sit by the beautiful fire table, or relax in the hot tub, and take in the gorgeous sunset view, over the water below, maybe even see a blue heron fly by. Step down to your private swim dock, perfect for fishing and crabbing, also includes kayaks for more fun in the sun.

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Fall/Winter promo: Book two nights, get one free on midweek stays (Monday thru Thursday)! Book two nights, get 50% off third night on weekend stays. Send a message after booking, and the promo night will be added. Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) Message for multi-night and monthly rates.

Cozy Cottage close to Beaches & Solomon’s Island

Explore Southern Maryland in a cozy, renovated Victorian cottage on a quiet, private cul-de-sac surrounded by trees. You’ll be close to a lot of fun places! 5 minutes to Vera’s Restaurant & marina 6 minutes to Calvert Cliffs State Park & Beach (3.1 miles) great for shark teeth sifting 7 minutes to Flag Ponds Nature Pk & Beach 2.8 miles 12 minutes to Annmarie Sculpture Garden 7 miles 12 minutes to Calvert Marine Museum 8.2 mi 16 minutes to Solomon’s Island 9.5 miles

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Relax with the whole family at this serene, waterfront retreat on Mill Creek — complete with a hot tub, private dock, kayaks, and nearly 360 degrees of beautiful water views! Cozy up inside or grab beach chairs, sand toys, and books offered for your beach days and return home to grill and dine al fresco on the deck overlooking the water. Let the kids burn off energy on the side yard’s play structure while you relax on the patio by the shoreline, drink in hand.

Beachfront Escape with Horizon Views of the Bay

Modern beachfront Panabode log cabin with sweeping Chesapeake Bay views. Relax on the deck, in the hot tub, swing, beach, or by the fire pit. Enjoy kayaks, paddleboards, shallow water, landscaping, and wildlife sightings. Main bedroom has king bed and ensuite bath. No pets, visitors, or street parking. Guests must bring linens, towels, and remove trash. Peaceful beachfront escape with modern, rustic charm, and unforgettable views.

Riverside Haven w/ Hot Tub

Unplug and unwind at Riverside Haven, a cozy waterfront cabin for two overlooking the Chesapeake Bay. Dog-friendly and designed for comfort, it’s perfect for couples or solo travelers. Enjoy complimentary coffee, free Wi-Fi, a private hot tub, a fire pit and access to a small public beach next to the property. Wake up to stunning sunrises and relax in peaceful, natural surroundings—Riverside Haven is your perfect coastal escape.