Holiday rentals with a hot tub in Annapolis

4.95 out of 5 average rating, 292 reviews

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

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.

4.87 out of 5 average rating, 106 reviews

A stylish dining area is showcased, featuring a long table set for a meal. Generous seating is provided by a custom velvet upholstered bench with decorative pillows, while a modern light fixture hangs above. Large windows allow natural light to fill the space.

Home in Bowie

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

*PLEASE READ OUR LISTING AND HOUSE RULES IN, PRIOR TO BOOKING OUR HOME. SEASONAL POOL/ HOT TUB DATES* Welcome to your beautiful and spacious home away from home! Featuring 4 beautifully decorated bedrooms and 2.5 bathrooms, each designed with comfort and style in mind. Relax in our spacious living areas, take a plunge in the pool & hot tub or lounge by the fire pit in the huge backyard! Experience luxury and comfort in our beautiful home and make unforgettable memories with your loved ones!

4.87 out of 5 average rating, 191 reviews

A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.

Home in Annapolis

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!

5 out of 5 average rating, 197 reviews

Home in Shady Side

Luxe Winter Retreat- 5 Star

Winter at The Cottage at Silver Water is calm, clear, and quietly beautiful. Snow-dusted views and crystal-blue skies frame the Chesapeake as migrating waterfowl glide across the water. As the day ends, golden hour washes the bay in soft light, often finishing with a vivid winter sunset—quiet and unforgettable. Inside, Nordic-inspired design, a cozy fireplace, and sumptuous bedding create a warm retreat for deeply restorative rest. Discover why so many guests return by reading our reviews.

4.94 out of 5 average rating, 203 reviews

A spacious bedroom is showcased with a king bed dressed in neutral linens and accented by two blue decorative pillows. Natural light filters through the two windows beside the bed, and a coastal-themed artwork adorns the wall above. Two bedside lamps provide additional soft lighting.

Guest suite in Arnold

Affordable, Cozy Retreat 4 Miles from Annapolis

*NEW HOT TUB BEING INSTALLED (available after 3/16)* Escape to a cozy, modern retreat just 4 miles from downtown Annapolis. This intimate king suite offers a private seating area, kitchenette, & TV. The ensuite bathroom features a luxurious shower. Relax in peace and comfort after exploring Annapolis or attending local events. Please note that the pool and hot tub are closed for the season. Reach out anytime with questions or special requests—we’re happy to help make your stay memorable!

4.91 out of 5 average rating, 159 reviews

A relaxing hot tub is positioned surrounded by lush greenery and soft grass. Two wine glasses and a bottle are placed on a wooden tray, suggesting a tranquil atmosphere. The bubbling water is gently steaming under a clear blue sky.

Home in Annapolis

The Naval Nook 1.3 mi. from Downtown Annapolis

Welcome to your home away from home at the Naval Nook! ~ 4 min. Uber from Downtown Annapolis ~ Brand New Hot Tub ~ Cool Electric AC ~ King Bed ~ Sunroom with Daybed and Trundle ~ Zero Gravity Chairs ~ Outdoor Dining table ~ Beautiful Spacious & Comfortable bedrooms ~ Couch w/ Queen Bed pullout ~ 4 Smart TVs in each bedroom & living room ~ Tiled showers w/ shampoo & conditioner ~ Fully equipped kitchen ~ Luxurious Linens ~ Luxury Electric Fireplace Airbnb Registration #: STR23-145225

5 out of 5 average rating, 168 reviews

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

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**

4.99 out of 5 average rating, 138 reviews

A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.

Home in Edgewater

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

4.99 out of 5 average rating, 275 reviews

An outdoor patio area features a hot tub, a dining set, and a grill. A shaded seating area is furnished with cozy couches, while a colorful game board adds a playful element. Lush grass covers the ground, creating a welcoming space for relaxation and enjoyment.

Home in Silver Spring

Modern 3-Level Stay| Hot Tub | Game Room | Parking

Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

5 out of 5 average rating, 118 reviews

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

4.84 out of 5 average rating, 120 reviews

Villa in Annapolis

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Escape to Serenity: Chesapeake Bay Oasis. Experience the ultimate Chesapeake Bay retreat - stunning 6-bedroom, 3-bath water-view villa, perfectly suited for family reunions & special gatherings. Enjoy breathtaking bay views, steps from the water's edge, with gated 240’ pier, sandy beach, protected swim area, picnic tables, BBQ grills & children's playground. **6-person Outdoor hot tub - current temp is 102•F**

4.87 out of 5 average rating, 117 reviews

A wooden dock extends into the water, equipped with boat slips on either side. Lush green grass frames the foreground, while calm waves ripple in the background. The scene is set under a soft, cloudy sky, providing a serene waterfront view.

Home in Pasadena

Beautiful Waterfront Home With Theater Room

This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!

Popular amenities for rentals with a hot tub in Annapolis

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

4.97 out of 5 average rating, 38 reviews

Aerial view of a waterfront home situated at the edge of Carr's Creek. Lush greenery surrounds the property, with serene water stretching towards the Chesapeake Bay. Boating docks are visible, along with trees displaying autumn colors along the shoreline.

Home in Deale

Beautiful Waterfront Escape w/ Gorgeous Views

4.99 out of 5 average rating, 68 reviews

A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.

Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

4.95 out of 5 average rating, 21 reviews

The spacious living area features a warm wood ceiling and large windows overlooking the greenery outside. A comfortable sectional sofa and an accent chair are positioned around a rectangular coffee table, creating an inviting space. A modern fireplace stands elegantly against the wall, complemented by tasteful decor.

Home in Grasonville

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

4.99 out of 5 average rating, 78 reviews

A spacious backyard features a pool surrounded by a paved patio. Comfortable lounge chairs and umbrellas are positioned for relaxation. The two-story house with a deck overlooks the inviting pool area, flanked by lush greenery and colorful landscaping.

Home in Edgewater

Entire Beach House with Pool and Hot Tub

4.96 out of 5 average rating, 57 reviews

A modern kitchen features white cabinetry and stainless steel appliances. A large island with a marble countertop and gold-accented stools is positioned at the center. Sunlight fills the space through multiple windows, offering views of the surrounding nature.

Home in Glen Burnie

Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore

4.86 out of 5 average rating, 14 reviews

Home in Chester

Crab Alley | Waterfront Home + Hot Tub + Game Room

5 out of 5 average rating, 8 reviews

Home in Shady Side

Marsh-Front Waterfront Retreat w/ Hot Tub

5 out of 5 average rating, 40 reviews

An outdoor space is presented featuring a wooden deck surrounded by a lush grassy area. Brightly colored lounge chairs in yellow and blue are placed around a central fire pit. Shade is provided by large umbrellas, creating an inviting area for relaxation.

Home in Annapolis

USNA Home Steps to Stadium Dog-Friendly w Parking

Villa rentals with a hot tub

The master bedroom features a spacious bed with a decorative throw and a large window allowing natural light to fill the room. A comfortable chair is positioned next to a TV, while a neutral rug covers the dark wood flooring, creating a relaxed atmosphere.

Private room in Silver Spring

4.83 out of 5 average rating, 6 reviews

Private room with bath, share living room& kitchen

Villa in Severn

New place to stay

Private Luxury Spa Hot Tub Retreat with Ping Pong

A bright bedroom features a spacious bed covered in light bedding. A work table and a chair are positioned near a window dressed with curtains. A rug adds texture to the room, complemented by a minimalistic decor.

Private room in Silver Spring

4.69 out of 5 average rating, 13 reviews

Private room with work table & chair.

4.84 out of 5 average rating, 120 reviews

Villa in Annapolis

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Other holiday rentals with a hot tub

4.75 out of 5 average rating, 12 reviews

An inviting pool area is showcased, featuring a clear blue water pool surrounded by several sun loungers and umbrellas. A hot tub is situated at the edge of the pool, framed by lush greenery and open space, enhancing the serene outdoor setting.

Home in Saint Michaels

Summer Retreat — Pool, Hot Tub & Outdoor Oasis

4.96 out of 5 average rating, 83 reviews

A serene waterfront view is captured, featuring lush green grass leading to a private patio area with a hot tub. In the background, a rainbow arches over the water, framed by a cloudy sky. The cozy apartment stands nearby, enhancing the tranquil setting.

Guest suite in Annapolis

Bay View Studio Apartment

Townhouse in Butchers Hill

The entrance features a wooden staircase leading to the upper level, accented by a railing in a warm tone. Natural light floods the space, highlighting the stone flooring and a cozy seating area with a view of a stylish bar table in the background.

4.96 out of 5 average rating, 80 reviews

Stunning Home near Hopkins, Fells Point & Downtown

4.96 out of 5 average rating, 51 reviews

A serene outdoor space features two turquoise Adirondack chairs positioned on a grassy area by the water. A small white table sits between them. A fire pit is placed nearby, surrounded by trees, with a view of the calm water and distant houses.

Home in Dundalk

Waterfront Villa with Hot tub & theater/Game room

Guest suite in National Harbor

The exterior of the Wyndham resort is captured during twilight, showcasing a modern multi-story building with a rounded top and prominent signage. Balconies line the upper floors, framed by large windows. Surrounding trees add greenery to the urban landscape.

4.77 out of 5 average rating, 52 reviews

2 BR DELUXE with BALCONY ★ National Harbor Resort!

4.97 out of 5 average rating, 88 reviews

A spacious living area features a large sectional sofa arranged around a central area rug. The open layout includes a kitchen with modern appliances visible in the background. Ambient lighting and ceiling fans enhance the room's comfort and functionality.

Flat in Sparrows Point

Safe, quiet neighborhood close to downtown!

5 out of 5 average rating, 75 reviews

A charming tiny house is nestled among lush trees, featuring large windows that invite natural light. A spacious outdoor patio with two chairs and a fire pit provides an area for relaxation. The surrounding landscape is verdant, emphasizing the home’s secluded setting.

Tiny home in Rosedale

Tree house resort spa with sauna &heated salt pool