Holiday rentals with a hot tub in Anne Arundel County

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.

Bathroom · Outdoor spaces · Check-in

You'll Never Want to Leave

Walk 1 blk to Navy stadium/less than mile to city dock! With fabulous fenced in outdoor oasis for relaxing family fun - w/hot tub, outdoor bar w/flatscreen TV, fireplace, swing, bocce ball, ping pong, horse shoes, corn hole, & much more! Great family entertaining!!! hosted hundreds in our home & have most every amenity. A modernly decorated duplex home & much moreWe have it all! IT’s our HOME WHERE WE LIVE & have our belongings it is not an empty rental. Driveway & unlimited free street pkg

Outdoor spaces · Hot tub · Accuracy

Waterfront Oasis | Game Room + Fire Pit + Hot Tub

Picture yourself waking up to stunning views of the waterfront and spacious yard, while sipping a fresh warm coffee! Or enjoy a soak in the private hot tub while watching the sunset. For those sports fans we offer a 75" TV and pool table in the well-equipped game room. The outdoor area features a spacious dining setup, perfect for al fresco meals, and a fire pit for evenings of warmth and conversation. Whether you’re lounging by the water or entertaining, this property is the ultimate retreat!

Hot tub · Outdoor spaces · Laundry

Welcome to Heron House! Annapolis Waterfront Oasis

Heron House sits on the end of a pristine point surrounded by water everywhere you look. This enchanting waterfront retreat offers the perfect blend of tranquil charm and modern comfort and has been newly furnished and remodeled. Take in the spectacular views of the Severn River on the large deck with lounge seating and dining. Only 20 minutes by boat or by car to Annapolis’ City Dock, you can enjoy charming shops, historical tours, waterfront dining, and the Naval Academy. Bring your boat!

Bathroom · Outdoor spaces · Comfort

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

Hot tub · Bathroom · Decor

Celebrate Summer In Your Private Pool & Hot Tub

Lovely two acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing waterfront home is conveniently located eight miles from the Naval Academy and downtown Annapolis. **As of September 2026, Airbnb’s pricing structure applies a 15.5% host service fee to my rates.

Outdoor spaces · Bathroom · Layout

The General's House-Spacious Home w/Pool & Hot Tub

Look no further for your next vacation home in Annapolis! Relax, unwind or entertain friends and family in this spacious, updated 4-bedroom, 4 bathroom home in the heart of Annapolis. Our home features multiple spaces for entertaining both indoor and outdoors. You can swim in the pool, cozy up by the fire place or enjoy a movie night in our theater room. When you stay here, you will find this home provides everything you need to create lasting memories and truly enjoy your time in the area.

Hot tub · Outdoor spaces · TV

Charming City Retreat. Walk-harbor, eateries.USNA

As many others over the past decade, you will enjoy the year-round charm & convenience of this modern vintage cottage. Just blocks from shops, restaurants, pubs. Free parking. A secluded patio oasis for family gatherings, a chimnea & blankets to cozy up in, furnishings from Robert Redford's Sundance, modern appliances, ceiling fans, AC/heat, bathrooms with comfort-height toilets & grab bars, original pine floors. Corn Hole boards on site. Open USNA '29 '30 Com Wk. 6-night min applies.

Bathroom · Outdoor spaces · Laundry

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

Bathroom · Outdoor spaces · Getting around

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

Bathroom · Outdoor spaces · Indoor spaces

Pet-Friendly King Suite + Kitchen | Near Annapolis

Settle in just minutes from Annapolis in a spacious, pet-friendly guest suite with a king bed, full kitchen, separate living area, and year-round hot tub access. Perfect for couples, families, pet owners, and longer stays, Captain's Quarters sleeps up to 4 with a king bed plus a queen-size LoveSac sofa bed. Located just 4 miles from historic Downtown Annapolis and the U.S. Naval Academy, with private keyless entry, fast Wi-Fi, designated parking, and all the comforts of home.

Bathroom · Outdoor spaces · Comfort

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

Hot tub · Outdoor spaces · Breakfast