Holiday rentals with a hot tub in Annapolis

Cozy Retreat: Immaculate Clean, private place

Welcome to your Squeaky clean home! This neat & tidy room boasts a fully equipped kitchen, a clean bathroom with shower all for your exclusive use. You only share a wall with the main house. Ideal for solo travelers, couples or small families seeking an unforgettable getaway. Conveniently located on the corner for easy parking and access, it's situated in the most peaceful neighborhood and near metro and train stations for added convenience.Enjoy Netflix on the flat screen TV for your enjoyment.

Rare New Build Home w/Hot Tub, Fire pit, Game Room

*Rare listing* Nestled just outside of Washington DC, this stunning 5BR home offers an escape from the hustle & bustle. Sink into plush sofas as you unwind with a movie night or be greeted by a spacious patio area, complete with a hot tub & grill. Roast marshmallows & share stories with friends & family around the fire pit. In the mood for a city adventure? We’re located in between DC. Whether seeking relaxation, outdoor adventures, this is the perfect place to experience the best of both worlds

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**

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Hot Tub Haven: Annapolis Backyard Oasis

A serene escape awaits you at our cozy 4-bedroom retreat, just 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 Historic Annapolis has to offer!

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

Celebrate Summer by Your Private Pool

Lovely 2 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 water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay just 100ft away. Water views from most rooms plus treehouse vibes. 4 bed 4 full bath. Custom luxury upgrades, new kitchen aid appliances, rustic leather sectional sofas can sleep 4 more (14 total), outdoor grills, covered balconies, new 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!