Anne Arundel Area Rentals
From $268 per night (USD)VRBO
Modern Luxury Townhome - 2BR/2BA Near Fort Meade & BWI - Private Driveway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Jo’s Luxury Retreat is a modern and comfortable place designed for relaxing, working, or exploring DC, Maryland, and Vir ...
From $268 per night (USD)VRBO
From $483 per night (USD)Expedia
4BR Family Retreat Near Annapolis w/ Large Yard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4-bedroom home in The Anchorage waterfront community is just 12 minutes from downtown Annapolis ...
From $483 per night (USD)Expedia
From $463 per night (USD)VRBO
Charming WATERFRONT 3BR/2BA cottage - 20 mins to Annapolis/40 mins to downtwn DC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Your Chesapeake Bay vacation begins at this 3-bedroom cottage retreat just a short drive to Annapolis (20 mins) and down ...
From $463 per night (USD)VRBO
From $1698 per night (USD)Expedia
8,000 Sq Ft Luxury Estate Near Annapolis | Sleeps 32 | Pool, Theater & Pickleball
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 32
Welcome to your private 11-acre luxury getaway in Davidsonville, Maryland, just 10 minutes from Annapolis, 30 minutes fr ...
From $1698 per night (USD)Expedia
From $322 per night (USD)VRBO
2-bedroom house in nice Annapolis with cool AC breeze
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your cozy getaway awaits in Annapolis at this lovely house. With two comfortable bedrooms featuring a king bed and a ful ...
From $322 per night (USD)VRBO
From $755 per night (USD)VRBO
Cozy Waterfront Retreat w/ Dock, Hot Tub, Fire Pit, Game Room, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Picture yourself waking up to peaceful waterfront views, sunlight dancing on the water, and a spacious fenced yard just ...
From $755 per night (USD)VRBO
From $174 per night (USD)VRBO
Chic Laurel Extended Stay:Near Ft Meade•BWI•NSA
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
**LONG TERM LEASING ONLY*** A beautifully updated, modern home designed for comfort, work, and long-term living. Locate ...
From $174 per night (USD)VRBO
From $663 per night (USD)Expedia
Welcome to Getaway on the Bay | Your Waterfront Annapolis Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Water views. Room to gather. Coastal Maryland charm. Your perfect Annapolis getaway starts here. Welcome to Getaway on t ...
From $663 per night (USD)Expedia
From $1580 per night (USD)VRBO
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' histor ...
From $1580 per night (USD)VRBO
From $1917 per night (USD)Expedia
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience ...
From $1917 per night (USD)Expedia
From $610 per night (USD)VRBO
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, a ...
From $610 per night (USD)VRBO
From $634 per night (USD)Expedia
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and ...
From $634 per night (USD)Expedia
From $615 per night (USD)VRBO
Splendid home w/private pool, fire pit, several decks & balconies
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to this stunning five-level house nestled on a quiet and expansive 5-acre property in Annapolis, MD. With decks o ...
From $615 per night (USD)VRBO
From $1007 per night (USD)Expedia
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, an ...
From $1007 per night (USD)Expedia
From $680 per night (USD)VRBO
Splendid dog friendly home within walking distance to beach & play area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water vie ...
From $680 per night (USD)VRBO
From $747 per night (USD)Expedia
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this tw ...
From $747 per night (USD)Expedia
From $1477 per night (USD)VRBO
Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for gr ...
From $1477 per night (USD)VRBO
From $1713 per night (USD)Expedia
Renovated, dog-friendly home with private pool, hot tub & stunning backyard
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Whether you're planning to explore Annapolis, Baltimore, or Washington, DC, this four-bedroom home in Pasadena perfectly ...
From $1713 per night (USD)Expedia
From $1064 per night (USD)VRBO
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits ...
From $1064 per night (USD)VRBO
From $548 per night (USD)Expedia
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great wa ...
From $548 per night (USD)Expedia
From $572 per night (USD)VRBO
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis' cha ...
From $572 per night (USD)VRBO
From $508 per night (USD)Expedia
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled right on Severn River's shoreline, this waterfront retreat has been completely remodeled, redecorated, and boast ...
From $508 per night (USD)Expedia
From $1160 per night (USD)VRBO
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready fo ...
From $1160 per night (USD)VRBO
From $1940 per night (USD)Expedia
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pie ...
From $1940 per night (USD)Expedia
From $987 per night (USD)VRBO
Waterfront Annapolis Home Near USNA Stadium
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your waterfront Annapolis getaway! This inviting 3-bedroom home comfortably sleeps 6 and offers pea ...
From $987 per night (USD)VRBO
From $190 per night (USD)Expedia
Modern 1 bedroom - deck and water view, pet-friendly, water-privileged w beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lovely upper floor above a newly built detached garage. Spacious, safe neighborhood with a community beach and multiple ...
From $190 per night (USD)Expedia
From $286 per night (USD)VRBO
Water's Edge 2-bedroom house in charming Edgewater
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Edgewater at this terrific house. With two cozy bedrooms featuring queen beds, guests find plenty of space to ...
From $286 per night (USD)VRBO
From $806 per night (USD)Expedia
Waterfront Retreat Private Pier and Sunset Views
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: A waterfront home on Cadle Creek with its own pier and boat slip, a wide west-facing deck, and sunsets over th ...
From $806 per night (USD)Expedia
From $773 per night (USD)VRBO
Walk to Herrington Harbor: Spacious Bay Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
4,180 Sq Ft | Private Setting on a Wooded Lot | < 1 Mi to Marina | Library Tucked into the Traceys Creek community, thi ...
From $773 per night (USD)VRBO
From $480 per night (USD)VRBO
Port of Call: 5BR Modern Nautical Luxury
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to your Annapolis basecamp! Located in the private Anchorage community, by Annapolis Cove - a quick 12 minutes t ...
From $480 per night (USD)VRBO
From $698 per night (USD)VRBO
Annapolis Charmer - Perfect Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy a stylish stay in this beautifully updated, centrally located home featuring brand-new furnishings and a ...
From $698 per night (USD)VRBO
From $569 per night (USD)Expedia
6BR 3 Bath Waterfront Home w/ Private Dock & Views
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Waterfront escape with room for everyone! This spacious 6BR/3BA home offers serene water views, a private dock for kayak ...
From $569 per night (USD)Expedia
From $744 per night (USD)VRBO
Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
RENT-005995-2024-The Campbell House on Prince George offers the best of downtown Annapolis with a rare blend of historic ...
From $744 per night (USD)VRBO
From $577 per night (USD)VRBO
Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Yes! It really is the Perfect Vacation Rental in Annapolis!----Discover the perfect blend of historic charm and contemp ...
From $577 per night (USD)VRBO
From $1192 per night (USD)VRBO
Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
STR-250 -Escape to this spacious waterfront home in Arundel on the Bay, where sweeping Chesapeake Bay views surround you ...
From $1192 per night (USD)VRBO
From $462 per night (USD)VRBO
Historic District 2BR + Parking | Walk to City Dock & USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Stay in the heart of Annapolis’ Historic District, just a short walk from City Dock, the U.S. Naval Academy, restaurants ...
From $462 per night (USD)VRBO
From $359 per night (USD)VRBO
Private 2BR Apartment with Parking for Corporate, Medical & Military Stays
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR-270 - This private 2-bedroom apartment in Annapolis is a smart choice for mid-term renters seeking a clean, comforta ...
From $359 per night (USD)VRBO
From $1475 per night (USD)VRBO
Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR000259 - Just minutes from downtown Annapolis, this stunning waterfront home offers a private, upscale retreat for up ...
From $1475 per night (USD)VRBO
From $522 per night (USD)VRBO
Historic Downtown Annapolis | 2BR En Suites | Walk to USNA & City Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in the heart of historic downtown Annapolis at this charming 2-bedroom, 2.5-bath townhome on quiet Pinkney Street. ...
From $522 per night (USD)VRBO
From $635 per night (USD)VRBO
Spacious 4BR Annapolis Home | Near Navy Stadium & Downtown | Sleeps 9
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
STR-270 - Traveling to Annapolis with family or friends? Quiet Quarters offers the space, convenience, and comfort of a ...
From $635 per night (USD)VRBO
From $515 per night (USD)VRBO
Chapel Gate 3BR Steps to City Dock & Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Chapel Gate! Ideally located just outside Gate 3 of the U.S. Naval Academy and only a few blocks fr ...
From $515 per night (USD)VRBO
From $1359 per night (USD)Expedia
This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Ogelton Overlook. This 5 bedroom / 5 bathroom Coastal Charm sleeps 14 comfortably. This thoughtfully stylish ...
From $1359 per night (USD)Expedia
From $2441 per night (USD)VRBO
Gorgeous 6-bedroom Charming Annapolis Retreat
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Make yourself at home in this 6-bedroom Annapolis house. With 4 queen beds and 2 king beds, there’s plenty of space for ...
From $2441 per night (USD)VRBO
From $246 per night (USD)Expedia
Charming 1-bedroom cottage with AC in cozy Harwood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the beauty of Harwood from this 1-bedroom cottage.Located a short distance from Annapolis or Washington,DC it i ...
From $246 per night (USD)Expedia
From $576 per night (USD)VRBO
Luxury Spa Retreat Severn Hot Tub & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private Luxury Spa Retreat in Severn, Maryland. This elegant 3-bedroom home blends comfort, privacy, and upscale relaxat ...
From $576 per night (USD)VRBO
From $334 per night (USD)VRBO
Private & Quiet Cottage in West Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy, bright & private cottage in woods w easy access to town & highways; front porch & screened-in back deck w rocking ...
From $334 per night (USD)VRBO
From $483 per night (USD)VRBO
Private Retreat Severn, Fire Pit & Gazebo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This private luxury spa retreat is designed for deep relaxation, featuring inviting living areas with cozy seating and s ...
From $483 per night (USD)VRBO
From $1188 per night (USD)VRBO
2 Home, Private Luxury Retreat, Sleeps 20
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 9
Escape to a private luxury spa retreat in Severn, Maryland, just minutes from DC. Relax in the hot tub, gather around th ...
From $1188 per night (USD)VRBO
From $610 per night (USD)VRBO
Charming Coastal Retreat w Community Beach Dog-Friendly & Mins to Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis Family and Dog-Friendly Coastal Retreat | Walk to ...
From $610 per night (USD)VRBO
From $837 per night (USD)VRBO
Historic Bayfront Retreat - 4BR - Stunning Chesapeake Views - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bay Dreams, a beautiful historic home once known as the Waterfront Inn of Holland Point. Nestled along the C ...
From $837 per night (USD)VRBO
From $726 per night (USD)VRBO
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Relax after a fun Annapolis day in this well-appointed and spacious home. Centrally located in peaceful Murray ...
From $726 per night (USD)VRBO
From $431 per night (USD)Expedia
Cozy 3-bedroom cottage in water-privileged community minutes from Annapolis, MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in this charming home, just minutes away from Annapolis and the BWI airport. After your adventures to Annapolis ...
From $431 per night (USD)Expedia
- From $619 per night (USD)
VRBO
Walk to everything! Downtown Historic Annapolis “Arts District”
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
None delete delete delete delete delete delete delete delete delete delete delete delete delete deletebbbbbbvvvvvvvvvggg ...
From $619 per night (USD)VRBO
From $877 per night (USD)Expedia
Luxury Waterfront Home w Private Pier in Annapolis & Dog-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to All Decked Out, your dream escape in th ...
From $877 per night (USD)Expedia
From $550 per night (USD)VRBO
Bay Home in Annapolis with Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Complement your next outing to the Annapolis area with a stay at our beautiful waterfront home primely situated on the C ...
From $550 per night (USD)VRBO
From $1400 per night (USD)Expedia
Premium Modern Luxe Retreat Near BWI & Arundel Mills
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience modern comfort and luxury in this beautifully designed retreat located in the heart of Severn. Thoughtfully c ...
From $1400 per night (USD)Expedia
From $374 per night (USD)VRBO
West Annapolis Cottage | Porch, Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Bright, renovated, and perfectly positioned. This West Annapolis cottage has a screened porch for lazy morning ...
From $374 per night (USD)VRBO
From $739 per night (USD)Expedia
5 bedroom house with EV charger Near Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Experience coastal charm and modern comfort at Voyagers’ Nest, a spacious 5-bedroom retreat near downtown Annapolis and ...
From $739 per night (USD)Expedia
From $958 per night (USD)VRBO
Charming Annapolis Escape!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This Charming Annapolis property features 2 king beds and 2 queen beds; 2 living areas complete with large TVs. The Kitc ...
From $958 per night (USD)VRBO
From $479 per night (USD)Expedia
Beautiful Annapolis Home Near the Beach with a fitness room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Enjoy luxury coastal living perfect for families and friend groups in this newly remodeled Annapolis retreat. Located in ...
From $479 per night (USD)Expedia
From $1924 per night (USD)VRBO
Submariner's Gate - Historic 4-bedroom home in charming Annapolis with parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Step into Annapolis history at this lovingly restored 1867 home — said to be the first subdivision of the Hammond-Harwoo ...
From $1924 per night (USD)VRBO
From $606 per night (USD)Expedia
Modern Retreat w/ Fire Pit & Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Immerse yourself in the best that Annapolis has to offer while staying in this completely renovated, modern ranch getawa ...
From $606 per night (USD)Expedia
From $283 per night (USD)VRBO
Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Your Waterfront Escape on Marley Creek — a serene, light‑filled retreat that feels like home the moment you a ...
From $283 per night (USD)VRBO
From $535 per night (USD)VRBO
Charming Rowhome in Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church a ...
From $535 per night (USD)VRBO
From $319 per night (USD)VRBO
Pet Friendly Hideaway for 5 Close to Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Relax with the whole family at this peaceful place to stay. Tucked away on nearly an acre of land, this charming 3-bedr ...
From $319 per night (USD)VRBO
From $294 per night (USD)VRBO
Tranquil townhome with comfort and convenience
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Brand NEW Listing! First guests receive a special welcome discount. Family-Friendly Comfort & Convenience in The Groves ...
From $294 per night (USD)VRBO
From $660 per night (USD)VRBO
Quiet Woodland Lodge w Community Beach Access & Large Private Deck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to The Woodland Lodge Tucked at the end ...
From $660 per night (USD)VRBO
From $180 per night (USD)Expedia
Barefoot Cottage A Quiet Coastal Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a ...
From $180 per night (USD)Expedia
From $237 per night (USD)VRBO
Charming 3-bedroom townhome with AC in wonderful Laurel
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Unwind in Laurel at this lovely townhome. With three spacious bedrooms featuring a king bed, two queen beds, and a sofa ...
From $237 per night (USD)VRBO
From $601 per night (USD)Expedia
Green on Fleet 1 Block to City Dock & USNA w Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis Green on Fleet – Historic Annapolis Rowhouse (c.18 ...
From $601 per night (USD)Expedia
From $502 per night (USD)VRBO
Chic retreat steps to Water, Piers & Waterfront Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to this elegant, professionally decorated 4BR/3BA Chesapeake Bay retreat, just 3 blocks from the water. Designed ...
From $502 per night (USD)VRBO
From $861 per night (USD)Expedia
South River Estate 4BR Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Waterfront estate on the South River sleeping up to 10 guests. Enjoy a modern living room, dining area, sunroo ...
From $861 per night (USD)Expedia
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Light and airy cottage minutes to Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Colorful, light beach cottage minutes from historic Annapolis, Naval Academy, with a view of Round Bay. Three bedrooms, ...
Click For PricingVRBO
From $455 per night (USD)VRBO
DTA Row Home | Walk to City Dock & The Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay on one of Annapolis's most iconic streets in this renovated 3-level row home. Walk out the door and you'r ...
From $455 per night (USD)VRBO
From $1207 per night (USD)VRBO
GREENNEST is an ENVIRONMENTALLY FRIENDLY Waterfront home close to Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
The Timberpeg N. California Douglas Fir Post and Beam construction with Finnish Spruce ceilings is a beautiful stunning ...
From $1207 per night (USD)VRBO
From $516 per night (USD)VRBO
Cozy Townhome in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Modern Downtown Annapolis Retreat – Walk to Everything Welcome to 222 West Street – Unit A, a thoughtfully designed pri ...
From $516 per night (USD)VRBO
From $296 per night (USD)VRBO
Charming 3-bedroom home in Arnold’s water-privileged community near the park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to our cozy Arnold getaway! Located within walking distance of the kayak launch and the park with a large playgr ...
From $296 per night (USD)VRBO
Click For PricingVRBO
Historic Inn | Steps from Naval Academy & State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Located in the heart of Annapolis, this historic inn offers easy walking access to landmarks like the United States Nava ...
Click For PricingVRBO
Click For PricingVRBO
Historic Inn Stay | 1 Unit | Heart of Annapolis at State Circle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
Click For PricingVRBO
From $1125 per night (USD)VRBO
NEW! Private Luxury Spa Hot Tub Retreat with Ping Pong
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
**Suite Retreat 1: Your Private Luxury Spa Getaway Near Washington DC, Baltimore, & Annapolis ** _Escape to ...
From $1125 per night (USD)VRBO
From $713 per night (USD)VRBO
Annapolis Retreat | Outdoor Kitchen + Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to The Residence at Barefoot Cottage, a beautifully appointed 3-bedroom, 2.5-bath coastal retreat nestled within ...
From $713 per night (USD)VRBO
From $359 per night (USD)Expedia
Charming Living room in beautiful Annapolis with AC discount long stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Popular Annapolis, tents for $4000/night deeply discounted this bed & breakfast is a dream. Guests will find ...
From $359 per night (USD)Expedia
From $695 per night (USD)VRBO
Apartment Near Downtown Annapolis with Private Outdoor Space and Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to the Fitzgerald Suite – Lower Level, a p ...
From $695 per night (USD)VRBO
From $845 per night (USD)Expedia
Upscale Family Home Near Downtown Annapolis w Resort-Style Outdoor Spaces
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Upscale Family Retreat Near Downtown Annapolis | R ...
From $845 per night (USD)Expedia
From $139 per night (USD)VRBO
Charming barn in Annapolis for a relaxing getaway not a room just a mattress
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to this awesome barn in picturesque Annapolis. Guests enjoy a welcoming space featuring a cozy bathroom with a re ...
From $139 per night (USD)VRBO
From $386 per night (USD)VRBO
★ Odenton Retreat ★ EV Charger | Central to It All: DC, Annapolis & Balti...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A well-loved retreat with a strong track record of exceptional-rated stays since 2023 • 2-story Townhouse 3 Bedrooms, 2 ...
From $386 per night (USD)VRBO
From $640 per night (USD)VRBO
Two Historic Rowhomes in Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Two connected, historic row homes in the heart of Downtown Annapolis! Perfect for two families or larger group ...
From $640 per night (USD)VRBO
From $1252 per night (USD)Expedia
Luxe Row Home Steps to USNA Gate 3!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience a beautifully restored and well appointed Greek Revival home on a calm street directly facing the U ...
From $1252 per night (USD)Expedia
From $438 per night (USD)VRBO
Spacious, Charming 4BR, 2BA Glen Burnie Home, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Centrally-located charming Cape Cod home in the sought-after Glenwood neighborhood in Glen Burnie. Guests find plenty of ...
From $438 per night (USD)VRBO
From $365 per night (USD)Expedia
Cozy and serene one bedroom waterfront guest cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Perch at Heron’s Nest, a peaceful waterfront escape nestled along the banks of Valentine Creek. This cozy ...
From $365 per night (USD)Expedia
From $308 per night (USD)VRBO
Lakefront Home | FirePit | BWI | MarleyCreek River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Kid-Friendly Yard | LakeView | Kayak | Boat Dock| Airport | Patapsco River Unique Cottage: A luxurious, energetic upsid ...
From $308 per night (USD)VRBO
From $639 per night (USD)Expedia
Walk To Main St & City Dock from Historic Downtown Dog-Friendly Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Historic Downtown Annapolis Apartment | Dog-Friend ...
From $639 per night (USD)Expedia
From $232 per night (USD)VRBO
Cute, Cozy 2-bedroom house near Annapolis with water access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Hemlock Haven, a newly remodeled 2-bedroom, 2-bath rancher in Crownsville, MD. This cozy retreat features a ...
From $232 per night (USD)VRBO
From $412 per night (USD)Expedia
Historic Annapolis Home Walk to Downtown 3BR
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Stay in the heart of Annapolis in this beautifully restored historic home just a 5-minute walk from downtown. ...
From $412 per night (USD)Expedia
From $410 per night (USD)VRBO
Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Settle in by a cozy wood fire, walk the beaches at sunrise, visit Historic Annapolis museums, restaurants, and vibrant n ...
From $410 per night (USD)VRBO
From $350 per night (USD)VRBO
Pet-Friendly Edgewater Cottage Big Fenced Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Bring the whole crew — including the dog. This renovated 3-bedroom Edgewater cottage sleeps 6 and sits on a fu ...
From $350 per night (USD)VRBO
From $424 per night (USD)VRBO
Waterfront home: history, nature and comfort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Relax with the whole family at this peaceful home surrounded by forest, water, lush shaded lawns, gardens, his ...
From $424 per night (USD)VRBO
From $438 per night (USD)Expedia
Luxury 5-Star Chesapeake Bay Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Winter at The Cottage at Silver Water is calm, clear, and quietly beautiful. Snow-dusted views and crystal-blue skies fr ...
From $438 per night (USD)Expedia
From $514 per night (USD)VRBO
Eastport Cottage Only 4 Blocks to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the best of Annapolis from this charming and beautifully updated home in the desirable Eastport neighborhood. Loca ...
From $514 per night (USD)VRBO
From $1032 per night (USD)Expedia
Commissioning Week Spacious 4BR Home Near Annapolis & USNA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Spacious 4BR Home Near Downtown Annapolis & USNA Perfect for Commissioning Week Families Welcome to your ideal Annapol ...
From $1032 per night (USD)Expedia