Home Vacation Home Rentals By Owner In Annapolis, MD

Showing 180 Of 309 Vacation Rentals
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Exceptional(26)

$1978.14

/ Nightly
Private Vacation Home

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, Maryland, United States

Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and the Naval Academy, you can walk to many of the fun things that Annapolis has to offer, from fantastic restaurants, a wonderful range of shops, charming streets and historical homes. Annapolis was the first capitol of the United States, and many of the buildings from that era are open to the public for tours. Plus, with ample parking in the driveway, you never have to worry about finding a spot to park when you come home from the amazing attractions that are within easy driving distance, like the Smithsonian Museum in Washington, D.C. or the National Aquarium in Baltimore. brbrThe kitchen is truly a chef's dream, and if you are dining-in, there is everything you need to create sumptuous meals at home. There's a comfortable sitting area off of the kitchen, a small table (for 6) at the end of the living room, as well as a table that seats 14 in the dining room. Or, go outside to the lovely patio for an al fresco BBQ meal under the sun or stars. brbrThe garden is incredibly serene - come sit, or have a cup of tea tucked away on a mossy square, shielded by a grove of evergreens that offer year-round privacy from the passers-by. brbrThe large Primary Suite has a king bed, with a sitting area, and an en suite bathroom with a large free-standing tub, and gorgeous, honed soapstone shower. There is another king bedroom, with en suite bathroom, with a beautifully tiled shower. On the third floor, you will find two queen bedrooms, and a shared bathroom with a tub-shower. There is also a premium quality, very comfortable, leather sectional sofa in the sitting room on the lower level, as well as a mini-gym.brbrbrbrbr
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(29)

$615.6

/ Nightly
Private Vacation Home

Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Annapolis, Maryland, United States

This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (including gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the finished basement) and offers a combination of location and charm that is hard to beat!brbrHome has 3 spacious bedrooms that feature 2 queens, 2 twins, and a rollaway bed. There is also a private room in the basement equipped with a futon. The living room has a fully functional gas fireplace - perfect for staying cozy in the colder months. There is a newly renovated, fully equipped kitchen, complete with cookware, basic spices and oils, Keurig coffee maker (with complementary K-cups), and blender. The back patio offers a sitting and eating area as well as a grill for cooking outdoors, and the front porch, which faces attractive Prince George Street, is the ideal place for your morning coffee. Washer and dryer are available to guests as are two smart TVs, both set up with YouTube TV. The top floor offers a secluded working space and reading nook with a partial view of downtown Annapolis and the dome of the USNA Chapel — perfect for those looking for a quiet spot.brbrThere is a ring doorbell camera on the front of the house to protect the safety and security of guests.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(3)

$260.3

/ Nightly
Private Vacation Home

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis, Maryland, United States

Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen sized beds. Kitchen is fully equipped and boasts an open floor plan excellent for entertaining. TVs in each bedroom and in living room. Living room has space for a queen-sized air bed, which is provided in living room storage closet. Unit offers a/c and heating, pots and pans, dishes, silverware, drink ware, washer and dryer, wifi, bedding, coffee maker, dishwasher, fridge, microwave, stove, smoke alarm, patio with furniture, and plenty of free parking.brbrInterior features:brCentral A/C and heat (baseboard heaters can be used in addition) brCeiling fans in every room brAll windows have blinds with valances br9' ceiling heights brAll kitchen appliances included (Fridge, oven, microwave and dishwasher)brStackable washer and dryer br2 closets in master bedroom with double shelvesbrbrExterior features:brPatio area with patio furniture brEntry door has awning brOff-street parking brSecurity cameras with flood lightsbrbrNeighborhood features:brUnit is located in the Bay Ridge community. Close to multiple assisted living homes, marinas, and Downtown Annapolis. Suburban neighborhood is located on a quiet peaceful dead end road. Exterior of unit has security cameras and motion lights. A 5-minute walk to Quiet Waters Park, Eastport-Annapolis Neck Library, Hillsmere shopping center with restaurants (such as Annapolis Smokehouse and Grumps Cafe), the Dark Horse Bar, and Giant. A 10-minute drive to downtown Annapolis. Also nearby is Thomas Point Park. Ideal for boaters mooring at Bembe Beach Rd Yacht clubs or visiting family at Bay Woods Assisting Living or Naval Academy. Comfortable getaway at a much better value than hotels!br
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

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Exceptional(5)

$1275.14

/ Nightly
Private Vacation Home

Historic Luxury Steps to USNA + Vibrant Waterfront

Annapolis, Maryland, United States

Welcome to Fair Winds, a beautiful, spacious and sunlit historic home on gorgeous Prince George Street in the heart of downtown Annapolis. Less than a minute walk from both the vibrant downtown waterfront and the Naval Academy’s Gate 1, this home’s location quite simply cannot be beat. It’s perfect for Naval Academy families and Annapolis visitors alike!brbrThe SpacebrbrStep inside this beautifully restored home and be greeted by the original fireplace, updated to gas power to provide instant ambiance for the well appointed living and dining rooms. The living room has comfortable seating and a large flat-screen TV, while the adjacent dining room seats 8 to 10 comfortably. The fully equipped kitchen has stainless steel appliances, granite countertops, a gas oven range, fully stocked pantry and every appliance you could want to whip up a memorable meal for your guests. The kitchen even includes its own gas fireplace to add ambience to your meal prep!brbrUpstairs on the second floor you’ll find three bedrooms, including one featuring a full view of beautiful Prince George Street below as well as a large flat-screen TV. The second floor also features a laundry room with a back staircase leading to the kitchen for late-night snacking. This floor features two spa-inspired full baths, one with a luxurious bathtub to relieve stress any time of day. Look out on the state Capitol building as you head up to the third floor for two more bedrooms, one with beautiful views of Prince George Street, as well as another luxurious full bath.brbrFair Winds also features outdoor living at its finest. The front porch allows for cozy seating and people-watching along Prince George Street over a glass of wine. Meanwhile, a beautiful brick courtyard in the rear features cafe lights, an electric retractable awning and outside dining. A gas grill is available to create your own outdoor feast to be enjoyed surrounded by centuries-old brick in this oasis of privacy in the very heart of downtown Annapolis.brbrIf your priority is “location, location, location,” Fair Winds has that and more. Annapolis’s restaurants and shops are mere steps away, as are its wonderful historic sites. You won’t believe how close you are to everything – and by the time your stay at this beautiful property is over, you’ll feel like a local.br
Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps

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Exceptional(3)

$899.46

/ Nightly
Private Vacation Home

Annapolis Area Gem for Family and Friends

Annapolis, Maryland, United States

Large, spacious home perfect for family gatherings and special events! Riverfront neighborhood close to all Annapolis has to offer. Why spend over $200 per night for a tiny bedroom in a hotel across the street from a supermarket, when you can relax and unwind in luxury with your whole family or a group of friends and be close to major Annapolis attractions like the Renaissance Festival or Boat Shows brbrThis well-appointed home sleeps 10-12 comfortably with six bedrooms and a pull-out couch in the family room. Beautiful, private primary suite on the top floor. A second primary bedroom on ground floor with modern ensuite, perfect for grandparents or other special guests. Four more generously sized bedrooms in two separate wings of the house provide privacy. brbrSitting on over an acre of land, there are plenty of outdoor areas for you to enjoy during your visit. Over 1000 square feet of decking and patio space. You will have everything you need to create a memorable stay, including a patio with underdeck ceiling, outdoor shower, backyard with firepit, and a large outdoor hot tub.brbrOnly 8 miles from downtown Annapolis and 2 miles from the Renaissance Festival entrance, the location lets you enjoy the privacy of a quiet neighborhood while being only a short and easy drive to the City Dock, Navy Stadium, and other Annapolis Area events.brbrFully stocked kitchen, high-quality linens and towels included.
Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps

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$1679.59

/ Nightly
Private Vacation Home

Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill

Annapolis, Maryland, United States

Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into this century without losing the shipbuilding history that surrounds it.brbrThe photos truly do not describe this incredible home. Walk into the front door into the street-side formal living room on the main level - comfortable and cozy. Pass through the formal dining room to a magnificent loft-type sitting room that opens to the lower-level sitting room. Floor-to-ceiling, two stories of windows bringing the glimmering Spa Creek inside! Wander down the waterside staircase (there are two, one at the main entrance and this one) into yet another comfy lounge space. The lower level sitting room sits beneath the main level sitting room and shares the splendor of two-storied windows. Proceed into the family room and enjoy the big comfy seating looking out to the patio. There is also a beautiful big dining table here.brbrThe kitchen is a large space off of the family room with an island and casual dining table embraced by a fireplace. Unique tile work, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy a family dinner. It features a gas stovetop, oven, microwave, large double-door refrigerator with drawer freezer and drink station, Keurig coffee maker, dishwasher, toaster oven, and all of the pots, pans, and dishware you need for memorable family gatherings.brbrThere are three unique dining areas in this home! The cozy, warm kitchen dining area is perfect for casual dining and offers to seat everyone. The formal dining room on the main level offers beautiful views with pre or post-dinner cocktails on the adjoining balcony. The lower-level family room also boasts a long fabulous dining table for a casual meal and game night.brbrWalk out your doors to the patio, lawn, and water's edge which has a dock for your boat and water toys. From the top down, the main-level balcony features two cushioned chaises and a gorgeous fire table surrounded by more Adirondacks. The lower-level walkout opens to a stone patio with chairs, a lawn, and two deep water docks for your boat and water toys. Additionally, a propane grill is available for warm-weather barbecues.brbrTHINGS TO KNOW
Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps

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Exceptional(1)

$718.42

/ Nightly
Private Vacation Home

Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D

Annapolis, Maryland, United States

Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away from a private beach. Bring the whole family together and relish watching gorgeous sunrises and sunsets and taking in panoramic bay views from both levels of this home's wraparound porches. When you aren't lounging and watching yellow, pink, and orange hues fill the sky, head for the backyard, where a patio, ample seating, and a gas grill provide the perfect space to host cookouts! The screened, first-level wraparound porch is also a prime location to host crab feasts or barbecues while looking out onto the water.brbrSurrounded by mature landscaping, you will feel right at home when you pull into the driveway of this lovely house. Step inside and instantly notice the bright living area adorned with soft seating and a large TV. The full, well-equipped kitchen provides a pleasant space to play chef amongst the gleaming countertops and stainless steel appliances, whereas the large formal dining table is the perfect spot to eat as a family. brbrThe primary bedroom is a place of pure peace with its sprawling living quarters and spa-like en suite bathroom. Invest in self-care as you sink into the jetted tub or rinse off in the walk-in shower. The additional bedrooms are just as comfortable with their delicate color palettes and soft linens. Other interior perks include a large family room, central air-conditioning, and a private washer/dryer.brbrAnd when you want to get out and explore, check out the Annapolis Maritime Museum, Quiet Waters Park, Thomas Point Park, and the Night Hawk Golf Center.brbrTHINGS TO KNOWbrStreaming services are available with guests' own account(s).
Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps

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$1411.64

/ Nightly
Private Vacation Home

3-story, dog-friendly home near beaches with home theatre, grill & gaming tables

Annapolis, Maryland, United States

Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the lawn into a wooded area offers a very private and serene setting. A sizeable outdoor table with seating and a gas grill is perfect for warm-weather barbecues and meals alfresco.brbrThe spacious living room is adjacent and open to the kitchen with big, comfy furnishings. The sitting area off of the kitchen has more comfortable furnishings and a big-screen TV. The inviting den has leather furnishings and a TV. The open and updated kitchen features a full Sub Zero refrigerator and a full Sub Zero freezer, a fantastic island for prepping, and all the amenities. A separate dining room has seating, the kitchen table provides additional seating, and the kitchen island has stools.brbrThere is a big game room on the lower level with a pool table, air hockey, and foosball table. Adjacent to that is a huge room with a beautiful big bar, stage, and an impressive home theater. Additional perks include free WiFi, Comcast Xfinity cable TV, and a Sonos music system throughout the home.brbrTHINGS TO KNOW
Bed 6

Bed

Bath 5

Bath

Sleep 15

Sleeps

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$1911.14

/ Nightly
Private Vacation Home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis, Maryland, United States

On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pier will be a place for you and yours to relax and make memories. This beautiful Frank Lloyd Wright-inspired contemporary home with plenty of waterfront amenities boasts renovated interior and exterior spaces. brbrThe kitchen space has been designed to gather friends and family with top-of-the-line amenities for preparing and enjoying a gourmet meal. Two dishwashers and double refrigerators are an entertainer's dream. Use the dumbwaiter to easily send everything up to the third floor for dining with a view. The kitchen features a large island with seating and a dining table. Dine outside under the shade of large umbrellas. The third-floor rooftop has incredible views.brbrThe third-floor loft has an additional sitting area with a TV, a wine cooler, and a refrigerator. A warm, formal living room has a massive fireplace with reclining couches, water views, and a TV. An adjacent sitting room has a gas fireplace and seating with water views. The large covered front porch has big, comfy furnishings to snuggle into and take in the sunrises over the water.brbrEach of the bedrooms has been uniquely outfitted with your comfort in mind. The primary bedroom features a gas fireplace and water views, while one guest bedroom boasts bay views and an en suite bathroom.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brThe pool is open from May 20 until Labor Day.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.
Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps

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$1888.97

/ Nightly
Private Vacation Home

3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace

Annapolis, Maryland, United States

Perfect for family and group gatherings, this darling, three-story home near Severn River is calling your name! There is a beautiful paver patio with a backyard firepit surrounded by a wooded backyard and mature landscaping. Planning on hosting warm-weather barbecues There is a propane grill available for you! The screened porch off the kitchen (main level) features an outdoor dining table for six overlooking the backyard.brbrInside, the beautifully decorated open floor plan is perfect for entertaining and family gatherings. The comfortable family room adjoining the kitchen offers a smart TV, a large sectional sofa, two big and cozy chairs, and a wood-burning fireplace. The formal living room has inviting and comfortable conversational seating. When mealtime comes round, the big, bright cook's kitchen will be perfect for gathering! Some of the incredible appliances include a built-in microwave, Bosch dishwasher, French-door fridge, a JURA automatic espresso/latte maker, and an under-counter nugget ice maker. The eat-in kitchen table seats five and the large island with counter stools seats three. The formal dining room seats up to eight people comfortably! Additional perks include a wine refrigerator and a pantry that connects to the formal dining room.brbrThere is a fully-equipped basement apartment with Bedroom #6, a full bathroom, a fully-equipped kitchen, a full-size washer/dryer, and a living area with a TV and Ping-Pong table. Severn River can be seen from the third-floor loft bedroom depending on the season; water views are only a short walk down the street.brbrTHINGS TO KNOW
Bed 6

Bed

Bath 6

Bath

Sleep 12

Sleeps

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$848.11

/ Nightly
Private Vacation Home

Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D

Annapolis, Maryland, United States

Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a gas grill and a beautiful teak umbrella table with seating for six.brbrThe warm living area looks out to the Bay with a large comfy couch, swivel chairs, and a gas fireplace. Spend relaxing evenings on the amazing stone porch with Adirondack rockers - take in the famous Annapolis sailboat races from there and the second-floor balcony! The lower-level rec room has a big couch that converts to a queen sleeper, two comfy chairs with ottomans, a game table and four chairs, a large screen TV, and a wet bar. The large and bright kitchen is open to the rest of the main floor for continuous views of the Bay. All top-of-the-line, brand-new appliances, gorgeous cabinetry and surfaces, an eat-in kitchen bar with seating, a prep island with sink, and a wall-mounted kitchen TV. Enjoy your meals at the dining table for 10-12 or dine alfresco on the back deck on the large teak table with an umbrella for shade.brbrTHINGS TO KNOWbrThis home is not appropriate for events due to parking and neighborhood restrictions.
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

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