Property Walkthrough: 5106 Portside

Annapolis is one of the hottest tourist destinations on the East Coast. With close proximity to the water, seafood, tons of outdoor things to do, museums, kid-friendly activities, and friendly people, it is no wonder that people from all over the United States flock here to explore the rich culture.

If Annapolis is your destination for your upcoming holiday, it is time to start thinking about how you will get there, what you want to pack, and where you will stay. Luckily for you, we have the perfect house to rent during your short weekend getaway or long-term one-month holiday!

Ideal Location

5106 Portside is a beautiful Annapolis rental home that looks like something from a movie. This property is picture-perfect with a white picket fence, Victorian styling, trees in the front yard, and a walkway to the front door. Featuring three bedrooms, 2.5 bathrooms, and the capacity to sleep eight people, this is a great holiday home for couples, families, or friends.

Located just three blocks from the City Dock and close to the Eastport Bridge, this house combines the proximity of downtown Annapolis with a more suburban and upscale feel of Eastport. Containing an open floor plan with modern amenities and an airy interior, this home is spacious and luxurious.

Interior Amenities

The primary bathroom off the master bedroom is ideal for showering and relaxing after a long day — you can even get a bath in these stand-alone tubs on the marble tile floor! 5106 Portside has three spacious bedrooms with beds big enough for two people. If you want to invite another group of friends on your trip, you can even use the pull-out sofa in the living room for two more people!
After freshening up for dinner, you and your guests can enjoy dinner together at the lovely dining room table. After preparing a meal in the kitchen, with the large countertop, bar seating, free-range store, and modern light fixtures, head to the wooden dining room table. The table complements the wooden flooring and takes advantage of the open floor plan, making the dining room connect to the living room and the kitchen.

After a hearty meal, relax outside on the deck or head to the living room to catch something on TV or chat about the following day. Guests can sit in one of the comfortable chairs or snuggle up on the leather sofa with a leather footrest/magazine holder. The best part about this house is the open floor plan. You can easily walk from the kitchen to the dining room table to the living room while feeling like you are in one big room!

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Book This Annapolis Rental Home Today

For those who want a modern home that feels spacious, bright, and airy, we have got you covered. Use Rent AHA to find the home of your dreams for your upcoming Annapolis holiday!

Property Walkthrough: The Wardroom

The best vacation stories always begin and end with the best of vacation homes and when you choose Annapolis for your vacation getaway, choosing At Home Annapolis’ the Wardroom for the vacation chapter of your life promises to make this getaway a story you won’t be able to put down! Featuring 3 serene and tranquil bedrooms, 2.5 spacious baths, and a location that is close to all the excitement our city on the Chesapeake Bay can offer, this charming escape will be an integral part of your Annapolis experience, offering room for up to 10 guests to cohabitate in peace and harmony inside this Annapolis Vacation rental!

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Step into History

Built in the early years of the 20th century, the Wardroom is a sophisticated blend of historic charm and modern conveniences and as you follow the original wood floors into the depths of the home, you will never want to go home again. The living room is a bright space containing leather furnishings strategically placed opposite the state-of-the-art television hanging on the wall. A half-wall of brick is actually the back of the fireplace that provides warmth and charm in the dining space where happy vacation memories will be created over family feasts and board game adventures. The kitchen is a bright and modern space offering granite countertops and high-end appliances of stainless steel, including a gas range that will bring a tear of joy to the eye of every chef, amateur or professional. The half bath on the main level ensures no one will have to run up the wood stairs in the case of an emergency and completes the tour of the public spaces. Upstairs, the master suite offers a king bed topped with the most comfortable of mattresses and its own television for late-night entertainment options. The ensuite bath is surprisingly modern offering marble tiles, countertops, and two white porcelain vessel sinks that face matching mirrors. The second bedroom, this one centered by a full bed with painted iron head and footbed, shares access to the remaining full bath in which lies a clawfoot tub that will be the most popular spot in the home. The third bedroom also offers a painted iron full bed and shared access to the bath.

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So Much to Love in This Annapolis Vacation Rental

The Wardroom offers comfortable adventures that include alfresco dining at the umbrella-topped patio table that is perched cozily on a red brick terrace outside. Reserve this sweet home today and fall in love with everything that makes Annapolis one of the most popular vacation spots in the nation!

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Property Walkthrough: The Goat Pen

At Home Annapolis loves a bit of whimsy, such as what can be found in the name of one of our more popular properties, the lovely (and goat-less, we promise!) 4-bedroom, 3-bath Annapolis rental home affectionately referred to as the Goat Pen! Offering a tranquil comfort and an amazing location in the heart of historic downtown Annapolis, this beautiful home reveals surprises in comfort at every turn, including stunning views of the gardens of the William Paca House! Take a break from your television watching, pour yourself a cup of coffee, and prepare to lose yourself in the beauty of this special property that is destined to be your Annapolis dream vacation home come true!

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Welcome to This Annapolis Rental Home

A brick entryway, topiary bushes, and a charming seating area placed to the side of the front door are all hints that this home is something special. Open the wood and glass front door and step into a space that welcomes all who visit and follow the path of wood floors to the rooms beyond. A comfortable living room with a plush blue sectional, navy décor, and views of the state of the art television is the first space waiting to be discovered, but don’t sink into its depths yet, there is much more to see. Starting with a bar area tucked away in a quiet nook behind the dining room table and offering a built in stainless steel wine chiller, tile backsplash, and white stone counters that provide a calm contrast to the navy blue cabinets. A bright white farmhouse kitchens offers country cabinets, stainless steel appliances, and a breakfast bar, its expanse of white stone countertop fronted by two leather topped barstools. A secluded den off the kitchen features another plush sectional, a large television, and a quiet place to relax away from the “crowds” in a home that sleeps 19 comfortably. This room also offers access to a half bath and a fully equipped laundry room centered by front loading washer and dryer. A breakfast room offers seating for four at a glass topped table and the formal dining room provides seating for 8 more, ensuring everyone in the Goat’s Pen has a place to dine.

Each of the bedrooms in this beautiful space offer comfort and peace, with shiplap walls in one room, a queen bed with ensuite bath downstairs, and a king suite designed to impress. A king sleigh bed anchors the tranquil space offering views of the William Paca House gardens, and a clawfoot tub in the master bath promises to be the most popular spot in the home. Two Iron beds, one a full and the other a twin, grace the final bedroom and most bedrooms feature luxuriously appointed baths with designer details that include marble tiles, brass fixtures, and shiplap walls.

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Paradise Found

Offering comfortable charms and natural delights outside, the Goat’s Pen also features brick walkways, multiple seating and dining spaces, and two grills, 1 charcoal and 1 propane for al fresco meals that will never be forgotten. Reserve this special home today and find your joy in the historic city of Annapolis.

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Property Walkthrough: The Squadron’s Landing

When you are looking for a grand adventure, having the perfect home to come back to each night adds to the wonders of your getaway, especially when your journey brings you and your large family to Annapolis! Our Squadron’s Landing home manages to be cozy and comfortable as it offers 6 bedrooms, 6.5 bathrooms, and a backyard pool destined to be the hangout spot for you and 14 more of your favorite people. This guide to its charms will be all the convincing you need to click the book now button today and stay in this Annapolis vacation rental!

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A Private and Peaceful Annapolis Vacation Rental

This special property, constructed in 2014, has all the charm of an old farmhouse combined with the modern amenities travelers need today! A spacious living area filled with plush furnishings, bookshelves jam packed with books and games, and a state-of-the-art television brings pleasure to all who relax within its boundaries. A sleekly modern kitchen offers high-end appliances in stainless steel, granite countertops, and a cheerful ambience that may make you want to cook a meal, even though you are on vacation! Offering multiple places to enjoy the meals you prepare, you can choose to sit at the dining room table located just steps away from the fully equipped kitchen or on the covered and screened-in deck that overlooks the lake; the views at sunrise and sunset from this spot promises to be one of the sights you remember most!

Serene bedrooms help sleep come easy each night, a deep slipper tub in the master bath will soothe tired muscles, and a hanging swing outside one of the bedrooms are just more reasons your large group will absolutely fall in love with the magic of The Squadron’s Landing! A rec room on the pool level gives guests more ways to be entertained, offering a wet bar, pool table, and loads of soft and fluffy pool towels to dry off with after fun by the pool! A kid’s themed bedroom with a toy basket filled with toys and bunk beds where the littles will whisper, giggle, and share secrets until sleep overcomes them is a cheerful and happy space, and separate guest quarters allow multiple families to travel together, retreating to their private space when the vacation gets a little too crowded.

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Relaxation and Charm

Book The Squadron’s Landing today and discover how vacation dreams really can come true!

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Property Walkthrough: The Master Shipwright

The homes that make us happiest seem to be the ones where the sea beckons, and although our At Home Annapolis Master Shipwright property is not on the sea, or even on the bay, its proud perch on the banks of Spa Creek will bring you peace when your travels bring you to the beautiful and historic city of Annapolis! Offering 4 bedrooms with turn of the century charm and 4.5 baths with modern conveniences, this special Annapolis vacation rental property is destined to be the highlight of your vacation escape.

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An Annapolis Vacation Rental Updated for Your Comfort

The reality of most older homes is that in spite of their charms, they are not very “user friendly,” but with the Master Shipwright, the opposite is true, and this property shines in all ways! A cheerful country kitchen decorated in shades of sunshine and the sea features high-end appliances of stainless steel, including a gourmet gas range that is a chef’s dream come true! The living room sports a jaunty nautical décor with ships gracefully crossing the walls above an overstuffed sectional topped with a white slipcover, and a brick fireplace keeps guests warm on chilly winter nights. A second sitting room offers a state-of-the-art television and more nautical décor, and the dining area has its own room and is dominated by a large wood table and views of Spa Creek through a wall of windows.

A large deck takes up the expanse of the back of Master Shipwright and features multiple seating areas (including one with a gas firepit and sparkly glass “coals”) and another dining table at which meals promise to taste even sweeter as you dine, chat, and enjoy the views of the creek. Two docks located in its deep waters allows for boating adventures, so be sure to check out the rental companies in the area if that type of adventure excites you! A barbecue grill can also be found out on the deck, and when the weather is nice, there is nothing more wonderful than enjoyable than devouring your favorite meat or seafood out here in this space, watching the activity on the creek and feeling the tranquility the body of water imparts.

As the daylight fades and thoughts of sleep begin to enter your mind, the bedrooms continue with the theme of peace, tranquility, and life on the water, offering comfortable mattresses and soft linens, and more of the sea blue accents found throughout the house. The third floor offers attic space that has been finished out and is furnished with a row of single iron-framed beds that give the room the feel of an old Maine camp, only a lot more comfortable!

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Find Your Joy

Accepting pets on a case by case basis, the joy of family and the sea intertwine at the Master Shipwright making your Annapolis vacation shine bright. Reserve this sweet property today!

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Property Walkthrough: Bella Chateau

When you really want to live it up in style during your Annapolis vacation, choose At Home Annapolis and our stunning 5-bed, 4.5-bath Bella Chateau home to do it right! Offering a list of luxury amenities too long to name here and a charming farmhouse décor your entire family will feel welcomed in, this beautiful Annapolis rental home is located just a block away from the world-famous Chesapeake Bay. Our guide to its charms will give you a peek into what life is like when vacation dreams come true.

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A Joyful and Warm Annapolis Rental Home

You’ve chosen a vacation home, as opposed to a hotel room, for charm, space, and style, and Bella Chateau really shines, as it offers all three qualities. Follow floors made of wood to any of the three sitting areas found in the space, including a living room with a fireplace and grand piano, a sitting room with leather furniture and a state-of-the-art television, a theater room that comes complete with a home theater and a private stage sure to be enjoyed by the budding actors in your family. A game room featuring a pool and foosball table promises to be the center of entertainment, that is, assuming you can drag your spouse and cousins away from the custom bar tucked away in the corner of the rec room! The separate dining room is a formal affair featuring an antique sideboard filled with the serving dishes you may need for fancy dinners with the family, and the farmhouse kitchen is a chef’s dream, offering marble countertops, high end appliances, and custom cabinets painted a cheerful sea blue. Soak away the aches and pains from your travels in the master bath’s deep and luxurious tub, sit and sip your favorite wine on the back porch overlooking a peaceful forest. At night, when the sun sinks below the horizon and the sky is alight with the twinkling of a billion stars, sleep comes easy in our peaceful bedroom retreats.

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The Chateau of Your Dreams

Every day is a new venture in wonderful when you choose Bella Chateau for your vacation accommodations, where the charm of country meets the excitement of a thriving town! Reserve it today and spend your days exploring the beauty of historic Annapolis and your nights ensconced in luxury and style that could only be brought to you by At Home Annapolis.

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Property Walkthrough: The Patrol Ship

Offering the charm of a Nantucket cottage combined with the sleek style of a modern escape, The Patrol Ship is one of our more popular family homes and may be the perfect sanctuary for your Maryland Adventures. Featuring four spacious and tranquil bedrooms, two baths, and everything you need to ensure your stay with us will be one you never forget, The Patrol Ship is located close to the Navy-Marine Corp Memorial Stadium, making it perfect for Naval Academy family. So go ahead, walk up the four steps that lead to the wide covered front porch and open that cheerful teal front door and let’s explore what is quite possibly the Annapolis vacation home of your dreams come to life!

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An Annapolis Vacation Home Designed for Families

The most important people in your life are the ones who are a part of your inner circle, and At Home Annapolis recognizes their importance, providing homes that celebrate them. Once inside The Patrol Ship, its open concept floor plan reveals all, and as you move from room to room, exploring its charms, you will immediately feel welcomed and at home. The living room, filled with a plush sectional topped in a soft chenille, a state-of-the-art television, and a warm ambience that invites you to sit down and stay a while, peeks into the fully equipped kitchen, which looks over the dining room, the heart of the home. Wait for the morning meal at the granite-topped breakfast bar, keeping the cook of the day company as he or she rediscovers the joy of cooking as they prepare the meal on high-end stainless steel appliances. The dining nook tucked away in the corner is where raucous games of Candyland and Monopoly will be played with the younger generation, and family dinners will be loud events in which everyone laughs, chats, and of course devours the home cooked meals. Outside, a large wood deck and fenced-in backyard offers multiple places to sit, sip, and watch the sun set over the horizon, and as each day ends, sliding between the silky soft linens that top the premium mattresses in each of the four bedrooms promises to be the best part of your vacation escape.

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Book The Patrol Ship Today

This glimpse into your upcoming Annapolis getaway can become a reality when you reserve The Patrol Ship today and start planning the family vacation of your dreams!

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Property Walkthrough: KR Beach Club

When you are looking for an Annapolis vacation that is a far cry from the ones of your youth, you might want to take a peek at our At Home Annapolis KR Beach Club 7-bedroom, 5.5-bath vacation estate. Offering comfort, luxury, and a prime real estate spot on the Severn River, this special property is the home you have always dreamed of owning, and for one week, it can be all yours! This walkthrough is designed to give guests a clearer picture of what to expect from the vacation home of their dreams—enjoy!

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Southern Charm in This Annapolis Vacation Rental

In the movies, Southern homes usually have a tree-lined driveway leading up to a columned brick estate, and our KR Beach Club property offers just that! It is just the beginning of the wonders you can expect from this special property. As the door opens to reveal a tiled foyer with mahogany painted walls, you will begin to realize this is not going to be an ordinary getaway. Step down four steps into a charming living room painted in a cheery yellow. The coffered ceilings add a touch of elegance to a room filled with plush sofas and chairs, a fireplace, and in the corner, a baby grand piano that will provide hours of entertainment. Tucked away in another corner you will find a game table surrounded by four padded chairs, behind which stands a set of French doors leading out into a manicured backyard, and beyond that, the Severn River.

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A formal dining room features an heirloom dining table that easily seats eight, a wooden wine cellar, and a crystal chandelier that will make you feel as if you have stepped into a movie set, especially as the oversized window framed in red curtains offers even more views of the Severn River. A farmhouse kitchen with white cabinets, granite countertops, and stainless steel appliances is open to a breakfast nook tucked away in the corner, offering banquet seating surrounding a large farm table.

The family room off the kitchen features another fireplace, more welcoming seating, a state-of-the-art television, and a wall of windows/doors that allow guests to enjoy the indoor/outdoor lifestyle we love so much! The public spaces of this generously sized property offer another den downstairs, a private sauna, and more incredible views from every room in the house. Comfy beds will cradle you, giving you the best night’s sleep of your life, and a wrap-around deck on the back of the house offers multiple places to sit, sip coffee or wine, and watch the fun taking place on the river. A private swimming pool is the perfect place to practice your cannonballs, and a private dock can keep your rented boat moored and at the ready when it is time to have your own fun on the water.

Back inside of this Annapolis vacation rental, each of the 7 bedrooms feature different themes, from the simple to the fantastic, and include a painted dolphin mural, window seats for reading as you stare out onto the water, and a nursery decorated in cool colors for the youngest members of your traveling party.

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Everything You Dreamed It Could Be

Remember KR Beach Club when it is time to book your vacation and your Annapolis escape is guaranteed to be a vacation you will never forget!

Property Walkthrough: St. John’s Adjacent

As special as the US Naval Academy is, it is not the only educational game in town, and if you have a friend or relative about to graduate from St. John’s College, our liberal arts college, our At Home Annapolis St. John’s Adjacent property may be the perfect place to stay when attending the ceremony! Offering 4 bedrooms and a whopping 5.5 baths, this charming Annapolis rental property has everything you need for up to 10 people to stay comfortably, so bring along your cousins, siblings, and grandparents and prepare for a celebration you will never forget!

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Southern Hospitality at Its Finest in This Annapolis Rental Property

The large veranda that takes up the width of this special property will give you the realization that this getaway will be different than all the others as it offers a place to sit and people watch in relative coolness and total comfort. Open the blue door and walk into a tiled foyer that hints at the treasures you will find inside. Wood stairs with a runner to soften the noise lead upstairs to bedrooms and bathrooms, but we will stick to the public areas for now. Off to one side of the hall you will find the living room, offering high ceilings, built-in bookshelves filled with books, and two seating areas. A piano, a conversation corner, and a fireplace can be found in one of the seating areas, while couches that are plush and soft are placed in front of a state-of-the-art television in the other.

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The bright white kitchen found at the end of the hall features updated appliances in stainless steel, granite countertops, and a center island with cookstove and four chairs for overflow seating at dinner or as a place for guests to sit and chat with the cook of the day. A separate dining room offers an impressive place to gather for games, conversation, and meals, featuring padded chairs that allow you to sit for long periods of time. Although the kitchen is often considered the heart of the home, we think this room is where life unfolds in most family’s lives!

As we head upstairs to the private parts of the home, take a moment to examine bathrooms with update fixtures and lovely soaking tubs as you start to explore bedrooms that are spacious, comfortable, and designed to give you the best night’s sleep of your life! This beautiful home was built in the 60s, and although it has been updated for your comfort and pleasure, the mid-century modern vibe still manages to shine through.

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Whatever Your Reasons for Traveling to Annapolis

Coming home to the creature comforts offered in our St. John’s Adjacent property promises to make every experience more exciting. Reserve your stay today!

Property Walkthrough: Waterside With It All

Not all vacation rentals are created equal, and as you begin to plan your unforgettable escape to historic Annapolis, you may find yourself wanting a home that shines brighter than all others—for example, At Home Annapolis’s exquisite 6-bedroom, 6-bath Waterside With It All property! Located on the banks of Lake Ogleton and offering spacious rooms filled with light, every minute of your stay promises to be memorable, especially as every member of your family is welcome. This Annapolis vacation home rental sleeps 18 of your favorite people and accepts your fur baby on a dog-by-dog basis; it just doesn’t get any better than this!

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Step Inside This Annapolis Vacation Home Rental

The warmth of wood floors polished to glowing perfection invites you to step inside and leave your troubles at the door. Follow the pathways to rooms filled with treasures. A large and bright kitchen on the first floor and another smaller one on the second floor gives multiple families traveling together the ability to seek private time when the world gets too people-y.

Even if there is only one master suite, per se, each bedroom has its own private bath, so there is no need to run into other family members while half awake and not ready to face the day! The master suite itself is a massive space offering seating areas next to a fireplace, large expanses of wood floors, and an en suite that includes a walk-in shower and a deep slipper tub which will be enjoyed even more with soft music playing in the background and perhaps a glass of wine to go with the book you are reading!

The living room doubles as an office offering a desk and bookshelves filled with books against one of its turquoise walls, and a set of slip-covered and oh so comfortable slouchy couches are placed opposite a wood burning fireplace. Naps taken here are destined to be ones you will remember fondly upon your return to real life, especially those accompanied by the sound of rain falling on the roof and the crackling of a fire. The dining area, dominated by a large dining table, offers the perfect spot for family feasts, games, and moments of quiet contemplation enjoyed over a morning cup of coffee or an evening glass of wine.

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Lake Life Rules

Because At Home Annapolis doesn’t believe in less is more, the exterior of this special place offers an exciting plethora of fun and adventures. Swim in the private pool, soak in the hot tub, gather around the fire pit, or simply sit and enjoy the activities taking place on the lake. Rent a boat and anchor it to your private dock, ensuring the fun doesn’t end at the border of your property; every minute of your lakefront adventures in Annapolis are going to be ones you will never forget. Rent our Waterside With It All property today!

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