Anne Arundel Area Rentals
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VRBO
Luxury Waterfront with Big Views 10 min from Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The perfect Commissioning Week House! Enjoy the views in this architectural gem- a modern, modified A-frame. It's a true ...
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Expedia
Old home with Million dollar view
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Old home with million dollar view. New bed & bedding. So many good restaurants nearby. Waterfront with deck & dock. Down ...
Click For PricingExpedia
- From $1750 per night (USD)
VRBO
Luxury Waterfront with Big Views 10 min from Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
The perfect Commissioning Week House! Enjoy the views in this architectural gem- a modern, modified A-frame. It's a true ...
From $1750 per night (USD)VRBO
- From $450 per night (USD)
Expedia
7 mins away from Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close ...
From $450 per night (USD)Expedia
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VRBO
Lovely 1 bedroom rental in downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to offer! The ...
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Expedia
Adorable 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the attractions ...
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- From $450 per night (USD)
VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $450 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Spacious Odenton Townhome: 21 Mi to Baltimore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy both comfort and convenience at this Odenton vacation rental! Boasting modern features and easy access to Baltimor ...
From $143 per night (USD)Expedia
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VRBO
Pier Relaxation! @ the Chesapeake Bay!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
Pier Relaxation with the whole family at this peaceful place to stay on the Chesapeake Bay! Fishing or crabbing from th ...
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- From $401 per night (USD)
Expedia
Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Severn View of Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $401 per night (USD)Expedia
- From $310 per night (USD)
VRBO
Modern studio apartment 5 minute walk to downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern efficiency apartment with king bed, seating area with 2 recliner chairs for watching TV. Set up for remote work ...
From $310 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Searenity Stays, a Cozy Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Walk to Chesapeake Bay, parks & playgrounds! Relax and enjoy your time with family and friends in this Chesapeake charme ...
From $249 per night (USD)Expedia
- From $975 per night (USD)
VRBO
Stunning, Large Historic Annapolis Home, Steps to Academy and Downtown.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
**Under New Ownership** Experienced owner with multiple properties. Owners live locally, property manager resides in Cit ...
From $975 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Cozy waterfront remodeled beach cottage, just steps away from the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful views of the Chesapeake Bay from the front porch of this wonderful home. 4 bedrooms and very large kitchen awa ...
From $425 per night (USD)VRBO
- From $161 per night (USD)
VRBO
Hideaway By The Bay - Sunroom, bay view, propane fire pit, 6ft tall wood fence
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Hideaway By The Bay! Make yourself at home, get nice and cozy and kick back by the Bay! As the host and hom ...
From $161 per night (USD)VRBO
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Expedia
NEW lovely studio apartment with onsite parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located place! (Two guests maximum) The space null. Other things to note Pl ...
Click For PricingExpedia
- From $695 per night (USD)
VRBO
Perfect Waterfront Getaway\/ Family Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to the perfect family home with 4 bedrooms, 3.5 baths, and large living rooms with comfy oversized couches. The ...
From $695 per night (USD)VRBO
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Expedia
Charming Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastp ...
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Condo Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This BRAND NEW condo house boat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best ...
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- From $303 per night (USD)
Expedia
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with other lis ...
From $303 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Indulge or be still near Naval Academy\/ Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Beautifully decorated apt. close to the Naval Academy /historic downtown Annapolis. East port too. Waterview. Amazing su ...
From $165 per night (USD)VRBO
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Expedia
Contemporary home away from home in very beautiful location.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious beautiful home, you will be cozy in this luxurious property with pool table,enjoy nature walks, club house and ...
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- From $1052 per night (USD)
VRBO
Newly renovated townhome with a fenced yard, gas grill, washer\/dryer, central AC
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Herons Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1052 per night (USD)VRBO
- From $2758 per night (USD)
Expedia
Riverfront home with dock, private outdoor pool, gas grill, deck & great views
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 9
Weems Shelby Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $2758 per night (USD)Expedia
- From $582 per night (USD)
VRBO
Lovely home with a deck, gas grill, AC, firepit, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Portside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $582 per night (USD)VRBO
- From $2284 per night (USD)
Expedia
Upscale multi-level retro home with large deck, washer\/dryer, and lovely patio
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $2284 per night (USD)Expedia
- From $1370 per night (USD)
VRBO
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1370 per night (USD)VRBO
- From $855 per night (USD)
Expedia
Huge deck overlooking water
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expa ...
From $855 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Cheerful 3-Bedroom House in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the ...
From $246 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Bayfront Home w\/Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Comfortable home with a million dollar view of the Chesapeake Bay. Pet friendly, outdoor hot tub, solo stove, and gourme ...
From $500 per night (USD)Expedia
- From $1800 per night (USD)
VRBO
Reno'd Home in West Annapolis: Great for Stadium Events, Boat Shows & Downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
West Annapolis is a neighborhood close to everything, but with peace and quiet in mind. Shopping and food options are c ...
From $1800 per night (USD)VRBO
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Expedia
Traveling Professionals-Entire Home+Parking+W\/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ideal for Long Term Stays! Well-Maintained open floor plan w/ 2,400 sqft and large windows that make the entire condo fi ...
Click For PricingExpedia
- From $627 per night (USD)
VRBO
Annapolis 4 BR House w\/ Cottage and Gameroom
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...
From $627 per night (USD)VRBO
- From $109 per night (USD)
Expedia
Studio w\/3 beds, 1 Queen, two twin, couch, pellet stove, full amenities, shower.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Spacious 900 sq foot private entrance basement with pellet stove, queen size bed, two single beds, couch, dresser and dr ...
From $109 per night (USD)Expedia
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VRBO
Annapolis Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious three level home in water privileged community of Cape St. Claire Maryland. Perfect for traveling health profe ...
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- From $169 per night (USD)
Expedia
Private First Floor of Duplex Walking Distance to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
The home is a upstairs/downstairs duplex with two separate and private units that have been lovingly renovated and resto ...
From $169 per night (USD)Expedia
- From $390 per night (USD)
VRBO
Charming 1926 renovated home in quite neighborhood perfectly situated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought out ...
From $390 per night (USD)VRBO
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Expedia
Waterfront Magic - 10 minutes from downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
A peninsula on the Severn River located in the beautiful neighborhood of Linstead. This home is a waterfront playground ...
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- From $266 per night (USD)
VRBO
North Beach Cottage - Walk to Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience life like a local with a stay at this 3-bedroom, 2-bathroom vacation rental cottage in North Beach. This 100- ...
From $266 per night (USD)VRBO
- From $627 per night (USD)
Expedia
House near Patapsco River
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Paradise Beach Retreat Whether you're planning to explore Pasadena, Annapolis, Baltimore, or Washington, DC, this four-b ...
From $627 per night (USD)Expedia
- From $120 per night (USD)
VRBO
My Annapolis Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FOUR WEEK MINIMUM STAY beginning July 1st. This fully furnished studio apartment has everything you'll need for a quiet ...
From $120 per night (USD)VRBO
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Expedia
Charming Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...
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- From $1765 per night (USD)
VRBO
7BR\/ 5.5 Bath Home AVAILABLE CW 2024, 2025
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
USNA Commissioning Week Rentals welcome! Perfect location for easy access to USNA events! A convenient 5 min drive from ...
From $1765 per night (USD)VRBO
- From $763 per night (USD)
VRBO
Annapolis Villa Aquamarine
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Annapolis and its very own Villa Aquamarine: your exclusive oasis awaits in this exceptional five bedroom hom ...
From $763 per night (USD)VRBO
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VRBO
Adorable House not far from Annapolis or Baltimore!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This is a great little house providing the respite you are looking for when visiting Annapolis or Baltimore. It's locat ...
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- From $350 per night (USD)
Expedia
Waterfront 2BR Guest House on Cypress Creek - Severna Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
STR00626 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $350 per night (USD)Expedia
- From $367 per night (USD)
VRBO
Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
From $367 per night (USD)VRBO
- From $153 per night (USD)
Expedia
Farmhouse-Style Home in Hanover!*Near BWI*
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a stylish experience at this centrally-located place. Freshly renovated duplex. Secluded and quiet with huge pr ...
From $153 per night (USD)Expedia
- From $1108 per night (USD)
VRBO
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1108 per night (USD)VRBO
- From $479 per night (USD)
Expedia
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a beautiful house for your stay in Annapolis! This large fully renovated house is just off West Street, 1.5 mil ...
From $479 per night (USD)Expedia
- From $428 per night (USD)
VRBO
Historic happy home, steps to Main Street, parking and lots of outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $428 per night (USD)VRBO
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VRBO
Fully renovated house in the heart of the Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully updated 3 bed/1.5 bath in Historic Annapolis, less than a mile from the main gates of the Naval Academy! Main bedr ...
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VRBO
Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
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- From $250 per night (USD)
Expedia
Charming Cottage with Hot Tub 1 Block from the Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy Annapolis with family & friends all year at this fully stocked and freshly renovated cottage just a block from the ...
From $250 per night (USD)Expedia
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VRBO
Garden home minutes from Baltimore and Washington DC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful living room with large window, Cozy indoor patio area, and the beautiful garden that rap around the home. Peac ...
Click For PricingVRBO
- From $305 per night (USD)
Expedia
Baltimore Area Vacation Rental w\/ Deck!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
You’ll feel right at home at this charming Baltimore Area vacation rental! Nestled in Pasadena, this 4-bedroom, 3-bathro ...
From $305 per night (USD)Expedia
- From $850 per night (USD)
VRBO
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...
From $850 per night (USD)VRBO
- From $346 per night (USD)
Expedia
HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Resort style community suitable for a get away from home 🏡 with everything at your fingertips tips. Home features: ...
From $346 per night (USD)Expedia
- From $406 per night (USD)
VRBO
Waterfront home with private pier mins to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Still available for 2024 Commissioning Week** Enjoy the magnificent waterfront views from this custom-built home with ...
From $406 per night (USD)VRBO
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Expedia
Newly-renovated waterfront home with private pier and all the bells and whistles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stay in this exceptional newly-renovated waterfront home with phenomenal views of the Severn River. Nestled in the desir ...
Click For PricingExpedia
- From $599 per night (USD)
VRBO
Family Friendly Staycation
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Family Friendly home one block from beaches, kayaking, sailing. Pet Friendly, Fully updated with two brand new remodele ...
From $599 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Brand-new Modern Pasadena Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy new home is located in the heart of Pasadena on a quiet end in Rivera Beach, just a few houses away from publi ...
From $315 per night (USD)VRBO
- From $85 per night (USD)
VRBO
Spacious Private Basement
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
New to Vrbo!! Private basement w/entrance. Great for PCS season. Just few miles away from Baltimore downtown, Ft Meade, ...
From $85 per night (USD)VRBO
- From $760 per night (USD)
Expedia
Oyster Harbor Waterfront Vacation Home -- Private Dock and Backyard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious and luxurious vacation home in Oyster Harbor, Annapolis. Features 4 bedrooms (7 beds), 3 full baths. A lively o ...
From $760 per night (USD)Expedia
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VRBO
Waterfront retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Separate waterfront apartment with private entrance. 900 square feet of living space which includes living room, large b ...
Click For PricingVRBO
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Expedia
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Modern Bay Dream
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
BRAND NEW LISTING! Enjoy the Chesapeake Bay in this brilliant 3-bedroom, 3-bathroom mid-century modern home nestled in ...
From $450 per night (USD)VRBO
- From $900 per night (USD)
VRBO
The place to be together! Linstead on the Severn River
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Two main floor bedrooms& baths and three bedrooms and one bath upstairs. Open and meandering decorator’s home full of en ...
From $900 per night (USD)VRBO
- From $785 per night (USD)
VRBO
Elegant waterfront cottage and guest house, garden setting, clubhouse and beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy waterfront views from every window, crabbing from the pier, sundowners on the wrap around porch, set in a private ...
From $785 per night (USD)VRBO
- From $404 per night (USD)
VRBO
Cozy private home 3 min walk to downtown, elevator, private driveway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a short walk to the center of Annapolis and harbor, this home includes a private driveway for 1 large vehicle (a r ...
From $404 per night (USD)VRBO
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Expedia
Stunning four-bedroom town home located in Millersville
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
This property is a Stunning four-bedroom town home that can accommodate up to 9 guests comfortably. The bedrooms are wel ...
Click For PricingExpedia
- From $299 per night (USD)
VRBO
Perfect Eastport Location, walk everywhere, Annapolis NO CLEANING FEE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $299 per night (USD)VRBO
- From $472 per night (USD)
VRBO
Gracie's Garden in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in a Heavenly Bed in the heart of Annapolis. Located 1 mile from downtown this garden apartment is completely ...
From $472 per night (USD)VRBO
- From $688 per night (USD)
Expedia
Family-friendly stunner with private patio and dog-friendly at On Cloud 9
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this stunning home in downtown Annapolis with all the things you will ever need: parking for 2 cars (1 on-sit ...
From $688 per night (USD)Expedia
- From $703 per night (USD)
VRBO
Waterfront home with beach on the Chesapeake Dog-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Be ...
From $703 per night (USD)VRBO
- From $585 per night (USD)
VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $585 per night (USD)VRBO
- From $211 per night (USD)
VRBO
The Lazy Crab Beach House - Free beach passes
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Lazy Crab Beach House just a few blocks from the Chesapeake Bay. Escape from reality and enjoy everythin ...
From $211 per night (USD)VRBO
- From $519 per night (USD)
VRBO
Pristine Waterfront Home with Expansive Views.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
**Monthly discounts only apply for Off-Season rentals (October-April) If relaxing in luxury on the water is what you a ...
From $519 per night (USD)VRBO
- From $822 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $822 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Free Wi-Fi + Complimentary Breakfast + Outdoor Pool | Near the BWI Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $217 per night (USD)VRBO
- From $720 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $720 per night (USD)VRBO
- From $695 per night (USD)
Expedia
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $695 per night (USD)Expedia
- From $750 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $750 per night (USD)VRBO
- From $118 per night (USD)
Expedia
Comfort and Convenience! Pet-friendly Unit with Fully equipped Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience wonderful conveniences that you should take advantage of including free Wi-Fi, onsite parking, fully function ...
From $118 per night (USD)Expedia
- From $540 per night (USD)
VRBO
Perfect Beautiful 6 Bedroom 4 bathroom Gem in Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Enjoy a Beautiful 6 Bedroom, 4 bathroom home in the capital of Maryland, centrally-located in the heart of Annapolis. Mi ...
From $540 per night (USD)VRBO
- Click For Pricing
Expedia
Modern Townhome In sought after area!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Minimum 30 night stay only... A modern 3 bedroom, 3 bathroom townhouse in a popular and sought after location. Less tha ...
Click For PricingExpedia
- From $449 per night (USD)
VRBO
3 bdrm close to city center, great yard & parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $449 per night (USD)VRBO
- Click For Pricing
VRBO
Historic house in Annapolis Arts District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Super host house rental in charming historic house, private and upscale, tucked away in the quiet President’s Hill neigh ...
Click For PricingVRBO
- From $179 per night (USD)
VRBO
18th Cent. Charm in Historic Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $179 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Secluded Cozy Cottage in Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $400 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Wonderful Chesapeake waterfront with private pier, large yard, kayaks, stand up paddleboards provided. Try fishing or cr ...
From $700 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Spacious Contemporary Waterfront home on Chesapeake Bay's South River
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This contemporary waterfront home sits on the Chesapeake Bay's South River. It is perfect for a vacation, work/school-fr ...
From $800 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront house with panoramic views from every room.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Windy Point. Wake up to breathtaking sun rises. Spend the day lounging by the water. Enjoy a paddle board rid ...
Click For PricingVRBO
- From $300 per night (USD)
VRBO
Comfortable Townhouse Minutes from City Dock and US Naval Academy!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Make this well-appointed townhouse your home away from home in the family-friendly Hunt Meadow community conveniently lo ...
From $300 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Sea La Vie
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful beach house right in the heart of it all...beach, boardwalk and restaurants. Walk out the door and you are sec ...
From $250 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Historic 3 Bedroom Downtown Annapolis Townhome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, ...
From $449 per night (USD)Expedia
- Click For Pricing
Expedia
Parking! Modern Cozy Home by DTA, Navy Stadium, and AAMC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Make yourself at home at our midcentury modern escape located right in the heart of Annapolis! This 2 bedroom 2.5 bathro ...
Click For PricingExpedia
- From $299 per night (USD)
Expedia
Beautiful home in walkable beach town near DC & Herrington Harbor Yacht Club!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Fantastic location for this remodeled 2-story home! A quick drive to Washington DC , Baltimore, Annapolis and the Natio ...
From $299 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Bay views with kayaks, bikes, fire pit, crabbing and more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Updated 3 bedroom, 2 bathroom private cottage is situated in a water community on the beautiful Chesapeake Bay. Take a ...
From $404 per night (USD)VRBO
- From $377 per night (USD)
VRBO
The Hideaway Spot- Waterfront w\/ Dock on Long Cove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Take a moment to unplug in nature with beautiful waterfront views! Perfect space for a family of four, two adult couples ...
From $377 per night (USD)VRBO