Vacation Rentals By Owner In Annapolis, MD

Showing 260 Of 436 Vacation Rentals

$285.0

Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.

Annapolis, Maryland, United States

Quiet furnished, double bed, kitchenette, private full bathroombrquiet and private studio in home 10 minutes from Downtown Annapolis, seperate entrance. easy access to all local restaurants and shopping.brno smoking, no pets. Wi-Fi available

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Sleeps

Exceptional(17)

$934.8

/ Nightly

Private Vacation Home

Winter Retreat Near Naval Academy+ Hot Tub!

Annapolis, Maryland, United States

◉ 5-min stroll to private beach br◉ Dock access for your boat br◉ Gourmet kitchen + private chef (by request) br◉ Stunning bay views from kitchen & bedrooms br◉ Ensuite baths in every bedroom br◉ 15 min to Naval Academy & Old Town br◉ 2 min to Starbucks & Giant br◉ Hot tub w/ water views br◉ Adirondack chairs & rocking chairs w/water viewsbr◉ Charcoal & propane grill br◉ Huge deck for sunbathing & lounging

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Bath

Sleeps

Exceptional(18)

$942.75

/ Nightly

Private Vacation Home

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis, Maryland, United States

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings! High end furniture! Hotel Luxury Mattresses! TV's in every bedroom! High Speed Internet!

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$427.5

/ Nightly

Private Vacation Home

DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!

Annapolis, Maryland, United States

This 2-bedroom non-investor house has everything you need for a great stay! We live there part time so it’s not an empty rental. Great kitchen, outdoor space, parking and location! Pet friendly with a doggy door and fully fenced yard. It’s a 3 bdrm house and we lock the primary suite for our 2 bdrm rentals. (The 3 bdrm is a separate listing). You have the house to yourself either: way-no sharing with owners or other renters. Amenities include a gas fireplace, dual zoned heat/ac, chimnea and wood, most streaming services, cotton linens and super comfy (practically new) beds to name a few features.brbrIf you want to cook for you mid this is the house for you. A substantial Napoleon grill (propane and back up provided along with every grill accessory you could want), double gas oven, every spice, herb condiment and utensil you could need. This is a fully appointed kitchen as we live there part time. When was the last time you went to a rental and had nice knives A cheese grater A rolling pin Saran wrap and aluminum foil It's all here. The open floor plan seats 14 for dinner: 8 dining chairs and 6 barstools!

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Bath

Sleeps

Exceptional(9)

$300.69

/ Nightly

Private Vacation Home

1 Block to USNA Stadium: Modern Annapolis Home!

Annapolis, Maryland, United States

Central Location | New Build | In-Unit Laundry | Fire Pit | 2 Mi to USNAbrbrSettle into this Annapolis vacation rental that suits both work and play. Just 2 miles from downtown, the State House, and the Naval Academy — and less than a half-mile from Navy-Marine Corps Memorial Stadium — this 2-bedroom, 1-bath home makes every trip easy. After a day of meetings, sightseeing, or game-day excitement, fire up the grill or gather around the fire pit to relax.brbr-- THE PROPERTY --brbrRENT-002085-2025brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrMAIN FEATURESbr- Wood-burning fire pitbr- Gas grillbr- TVsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig (coffee provided), microwavebr- Dishware/flatware, trash bags/paper towelsbr- Island w/ seatingbrbrGENERALbr- Free WiFibr- Central A/C & heat, ceiling fansbr- Washer/dryer, hangersbr- Linens/towels, hair dryerbrbrFAQbr- 1 exterior security camera (facing driveway)brbrACCESSIBILITYbr- Single-story home, 2 exterior staircases to enterbrbrPARKINGbr- Driveway (2 vehicles)br- Garage not availablebrbr-- THE LOCATION --brbr- 1 block to Navy-Marine Corps Memorial Stadiumbr- 2 miles to Downtown Annapolis, Annapolis City Dockbr- 2 miles to Maryland State Housebr- 2 miles to United States Naval Academybr- 22 miles to Baltimore/Washington International Thurgood Marshall Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 2 exterior staircases to enterbr- Your safety matters. This property features 1 exterior security camera on the home facing the driveway. The camera does not look into any interior spaces. It records video and sound when activated by motionbr- The garage is not available for guest use

Bed

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Sleeps

Exceptional(1)

$503.17

/ Nightly

Private Vacation Home

Eastport 3 bedroom Cottage: Walk to Downtown

Annapolis, Maryland, United States

Summary:brbrDiscover Annapolis from our charming Eastport cottage! This updated home comfortably sleeps 8 and is perfect for USNA events or a relaxing getaway. Enjoy a fully equipped kitchen, spacious backyard and a prime location just a 15-minute walk from Downtown Annapolis. Experience the best of historic Eastport with its marinas, waterfront dining, and local shops right at your doorstep. Your ideal family or group retreat awaits!brbrbrbrThe Space:brbrWelcome to our charming and updated cottage home, your perfect base for exploring all that Annapolis has to offer! Nestled in the historic Eastport neighborhood, this home is ideal for families and friends.brbrbrbrStep inside and you'll be greeted by a bright, inviting living area filled with ample natural light. The home offers several comfortable spaces to unwind, including a sun-filled sitting room and an additional living area on the lower level.brbrbrbrKey Features:brbr Fully equipped kitchen with modern stainless steel appliances and a breakfast bar.brbr Adjacent dining area for enjoying home-cooked meals.brbr Two full bathrooms with contemporary fixtures and complimentary toiletries.brbr Spacious and private backyard area, ideal for relaxing and outdoor entertaining.brbrbrbrSleeping Arrangements:brbr Master Bedroom: One plush Queen size bedbrbr Second Bedroom: One cozy Full size bedbrbrThird Bedroom: Two Double bedsbrbrbrbrGuest Access:brbrYou will have private and exclusive access to the entire home throughout your stay. This includes all interior spaces—bedrooms, bathrooms, kitchen, and living areas—as well as the private backyard. Enjoy the comfort and privacy of having the whole space to yourselves.brbrbrbrThe Neighborhood:brbrOur home is close to Eastport staples such as Vin909, Eastport Kitchen, Adam's Taphouse, Blackwall Hitch, and a short Uber Ride to Eastport Restaurant Row.brbrbrbrOther Things to Note:brbrFor your security and peace of mind, please be aware that exterior security cameras are present on the property. These cameras monitor the exterior of the home only and do not have views of any interior spaces.brbr brbrCity of Annapolis Rental License: RENT-000027-2026brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process for your convenience. While we will not be present during your stay, we are always available via the messaging app or phone if you have any questions or need assistance.

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Sleeps

Exceptional(3)

$551.3

/ Nightly

Private Vacation Home

Walk to DTA & USNA | Pet-Friendly Home

Annapolis, Maryland, United States

Summary:brbrBring the whole crew — dogs included. This 3-bedroom Annapolis home is walkable to Downtown, Navy tailgates, and USNA Stadium. Inside: bright living spaces, a sunny front room, breakfast nook, and sunroom overlooking the backyard. A king suite and two queens upstairs. Outside, the fenced yard has string lights, a fire pit, BBQ grill, and corn hole — everything for a perfect evening under the stars. Full bath upstairs, half bath on the main level. Free parking and high-speed WiFibrbrbrbrThe Space:brbrBEDROOMSbrbrThree bedrooms upstairs. The primary suite has a king bed. The other two bedrooms each have queen beds. Bedroom 2 includes a desk and workspace for remote work. Fresh linens provided.brbrBATHROOMSbrbrOne full bath upstairs with the bedrooms, plus a half bath on the main level. Towels, soap, and essentials provided.brbrKITCHENbrbrFully equipped with modern appliances, cookware, dishes, utensils, and everything you need for group meals. Open layout connects to the dining room which seats 6.brbrLIVING AREASbrbrThe main floor flows from the kitchen through a large dining room into the living room. A bright sunroom overlooks the backyard — the perfect morning coffee spot. Welcoming front porch with seating. Smart TV in the living room.brbrOUTDOOR LIVINGbrbrThe fenced backyard is the highlight. String lights, fire pit, BBQ grill, corn hole, and comfortable patio seating. Everything you need for an evening outside. Pet-friendly — your dog will love the space.brbrPARKINGbrbrFree parking on the driveway and street.brbrLOCATIONbrbrWalk to Downtown Annapolis, USNA Gate 1, and Navy-Marine Corps Stadium. Close to restaurants, shops, and the waterfront. Trolley stop nearby for getting around without driving.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcome — fenced backyardbrbrFull bath upstairs, half bath on main levelbrbrbrbrGuest Access:brbrPrivate entrance. Keypad on the front doorbrbrbrbrThe Neighborhood:brbrQuiet neighborhood tucked away off West St.brbrbrbrGetting Around:brbrWalkable to downtown Annapolis and the naval stadium.brbrbrbrInteraction with Guests:brbrI follow your lead!

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Exceptional(20)

$337.26

/ Nightly

Apartment

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

Annapolis, Maryland, United States

Treat yourself to the best while in Annapolis! Gorgeous 1500 sq. ft. custom designed waterfront apartment that takes full advantage of the lovely water views. 9 ft. ceilings throughout with walls of glass to capture all the exciting views day and night. The private entrance to the apartment is off of the 40 ft. covered waterfront patio for apartment guests exclusive use. Enjoy morning coffee on the patio and alfresco meals under the twinkling lights. Beautifully appointed apartment with a well stocked gourmet kitchen, sleep on silky soft bed linens, extra personal supplies & linens in the large bathroom, washer & dryer, 2 large bedrooms with a spacious living room, 40ft. private patio overlooking the South River in Annapolis. Off street parking is provided for up to 4 cars. The deep water pier is available for guests to use for fishing, crabbing or just enjoying the fascinating views of water and wildlife. You are welcomed to bring your boat with you. Community beach is nearby. Check with host for details. brLocated only a few minutes to historic Annapolis, restaurants, shopping and major medical centers and the US Naval Academy. br DC is only 35 minutes away and you can be at the ocean in less than 2 hours. Fabulous day trips and sightseeing in any direction you point yourself.

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$806.14

/ Nightly

Private Vacation Home

Waterfront home in Annapolis MD with private pier

Annapolis, Maryland, United States

Waterfront home, 2000 sq feet, in Annapolis, MD on Magothy River, overlooking Chesapeake Bay, Gibson Island with private beach and pier, short drive to downtown Annapolis, Bay Bridge, Naval Academy and Kent Island, great sunset/sunrise view and good for fishing.brGreat for a wide range of occasions: couples looking for a romantic weekend away.... family reunions.... girls weekend... sailboat show etc...Special event is welcome, the driveway can park 20 cars.br3 Kayaks and 1 stand up paddle are free to use.

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Exceptional(44)

$459.61

/ Nightly

Private Vacation Home

Historic DistrictCrab Cakes and Football

Annapolis, Maryland, United States

Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock and the Navy-Marine Corps Memorial Stadium. Private parking for 2 cars!brbrThere are seven restaurants within one block including:br- Thaibr- Italianbr- Irishbr- Unique Annapolis FarebrbrThis is the perfect spot to enjoy all that Annapolis has to offer. People who know the area know that having 2 parking spots is almost unheard of. We are located in one of the most sought after neighborhoods in Annapolis. The neighborhood has a very peaceful, quiet feel. The property had once been a long term rental but we decided we'd rather share it with people coming here to vacation. We live 5-10 minutes from the property so you can enjoy your privacy but we are available if you need us. brbr

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$501.03

/ Nightly

Private Vacation Home

Entire house on quiet street w/fenced yard—1 block from river, 3 from bay

Annapolis, Maryland, United States

Arundel-on-the-Bay is a private community on Annapolis Neck peninsula, and this home sits right in the middle. Ideal spot for stargazing, sunrises/sunsets, fishing off the pier, water sports, sunning at the beach, and relaxing strolls. 15 minutes from historic downtown Annapolis. You’ll have the whole house to yourself.brbrFishing Creek to the west, Chesapeake Bay on the east. Playground 1 block away.

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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

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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.

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$895.71

/ Nightly

Private Vacation Home

Cottage for Rent

Annapolis, Maryland, United States

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Sleeps

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

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Exceptional(1)

$596.87

/ Nightly

Private Vacation Home

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

Annapolis, Maryland, United States

Perfect home for families traveling to Annapolis! Your family will be close to everything when you stay at this centrally located Eastport home. Less than 2 miles to the Naval Academy and downtown Annapolis. Perfect family friendly home with plenty of space to visit your midshipmen at the Naval Academy or attend a game at the Navy-Marine Corps Memorial Stadium. Close enough to walk to the waterfront to enjoy the many bars, restaurants, boat tours, or sailing excursions. We have enough space to sleep 12 and a fenced in back yard for your dog. Experience your Annapolis home away from home in this 4-bedroom house. The bedrooms feature 1 queen bed, 2 full beds, 2 twin beds, 1 bunk bed, and 1 crib. The property also includes a cozy living room with a couch for additional sleeping space. Enjoy the enchanting and gorgeous surroundings while staying here. Our place is equipped for both long or short stays to make your stay one to remember.

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Exceptional(4)

$454.1

/ Nightly

Private Vacation Home

Marymont Cottage in awesome Annapolis walking distance to local pub!

Annapolis, Maryland, United States

Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming house features 2 full beds and 1 queen bed, perfect for a cozy getaway, Navy games, boat show, or commissioning week. With amenities like AC and heating, awesome outdoor grill bar and sink and stone fire pit in fully fenced backyard, Guests will feel right at home relaxing in the living room with a custom floor to ceiling stone fireplace. Spread out with optional sleeping in the TV Room. Plenty of off-street parking. Make your holiday one for the books with a stay at our place.

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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

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Sleeps

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.

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Bath

Sleeps

Exceptional(19)

$596.87

/ Nightly

Private Vacation Home

Chesapeake Bay single family home

Annapolis, Maryland, United States

Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront home on the Chesapeake Bay. with a 30 ft pier for fishing and crabbing. The community has a private neighbood beach within walking distance of home. Close to shopping, restaurants and entertainment. 6 miles from the Naval Academy, 30 miles from Washington, DC and Baltimore, Maryland.

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Rent a place that suits your needs

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View 341 Private vacation home

Most popular vacation rentals in Annapolis

Exceptional(19)

$1019.16

/ Nightly

Private vacation home

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis, Maryland, United States

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Exceptional(19)

$1203.20

/ Nightly

Private vacation home

All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Annapolis, Maryland, United States

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Exceptional(19)

$1131.86

/ Nightly

Private vacation home

Historic Eastport! Steps from restaurants, retail, and more.

Annapolis, Maryland, United States

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Sleeps

Exceptional(19)

$1105.72

/ Nightly

Private vacation home

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Annapolis, Maryland, United States

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Exceptional(19)

$1088.17

/ Nightly

Private vacation home

Annapolis History In Style Next to City Dock with Street Parking

Annapolis, Maryland, United States

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Exceptional(19)

$1083.00

/ Nightly

Private vacation home

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Annapolis, Maryland, United States

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Exceptional(19)

$1054.78

/ Nightly

Private vacation home

Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis

Annapolis, Maryland, United States

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Exceptional(19)

$1029.67

/ Nightly

Private vacation home

Brand New Spacious Luxury Home

Annapolis, Maryland, United States

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Exceptional(19)

$945.86

/ Nightly

Private vacation home

Huge deck overlooking water

Annapolis, Maryland, United States

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Sleeps

Exceptional(19)

$948.10

/ Nightly

Private vacation home

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

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Vacation Rentals By Owner In Annapolis, MD

$285.0

$934.8

$942.75

$427.5

$300.69

$503.17

$551.3

$337.26

$806.14

$459.61

$501.03

$1978.14

$615.6

$895.71

$260.3

$596.87

$454.1

$1275.14

$899.46

$596.87

Rent a place that suits your needs

Most popular vacation rentals in Annapolis

$1019.16

$1203.20

$1131.86

$1105.72

$1088.17

$1083.00

$1054.78

$1029.67

$945.86

$948.10

Most Popular Cities in Maryland