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From $438 per night (USD)
VRBO
Cozy 2br home w/ parking in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $438 per night (USD)
VRBO
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Expedia
Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nice 2 bedrooms / 1 bathroom appartment in the lower level of a single home, private entrance and patio in the back of t ...
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Expedia
From $299 per night (USD)
VRBO
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Quaint 2 BR 1 BA Guest House nestled in the trees by USNA stadium. Enjoy Annapolis historic charm in this rare 2 BR 1 BA ...
From $299 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Adorable waterside cottage with pool Beach community
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $428 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Calico Cottage Guest House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute-as-a-bugs ear West Annapolis guest cottage. In settled neighborhood just 1.5 miles from the Navy Stadium and less t ...
From $187 per night (USD)
VRBO
From $583 per night (USD)
Expedia
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $583 per night (USD)
Expedia
From $752 per night (USD)
VRBO
Stay close to USNA Stadium with screened-in porch and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to this charming Cape Cod on half an acre right outside downtown Annapolis. Just minutes to the Stadium, Naval ...
From $752 per night (USD)
VRBO
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Expedia
Waterfront
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Waterfront house on a point where the South River meets Boyd’s Point. House was built in 2021 with huge gourmet kitchen ...
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Expedia
From $303 per night (USD)
VRBO
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay ...
From $303 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
The Beachwood Cottage is located near Mayo, Maryland, on the western shore of the Chesapeake Bay. The property sits on R ...
From $377 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Relax in this 7-mins-Away E’thing Cozy Modern Studio-Near BWI,Arundel Mills etc
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming, modern studio/guest room in a house in the heart of Glen Burnie. Just couple blocks away from BWI airport, ama ...
From $145 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The owner has created your own slice of paradise in the Rose Haven community of North Beach. Walk to Herrington Harbour ...
From $472 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Private Cottage on gated estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapo ...
From $245 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Cute Bay Home/Fantastic View and Sandy Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cozy three bedroom home with two large decks overlooking the Chesapeake Bay -- and a beautiful sandy beach. The view is ...
From $349 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $436 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $642 per night (USD)
Expedia
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VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-r ...
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VRBO
From $608 per night (USD)
Expedia
Steps to Main St at Historic Home with Capital Views, Private Patio & Free Off-Site Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, ...
From $608 per night (USD)
Expedia
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VRBO
Retreat on Sage Brush Court (Basement Suite w/private entrance)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
- This Home away from Home 1 bedroom (queen bed) - kitchenette (no stove) - electric 2 burner hot plate - the couch c ...
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VRBO
From $731 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 c ...
From $731 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Anchor's Away in the Heart of Eastport!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
From $298 per night (USD)
VRBO
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Expedia
Entire Town House Close to DC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This is a over 2,000sq home with 4 bedrooms and 3.5 bathrooms. It is a 3 level end unit with a patio perfect for family ...
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Expedia
From $247 per night (USD)
VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $247 per night (USD)
VRBO
From $346 per night (USD)
Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's l ...
From $346 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Charming Downtown 3rd Floor 1 Bedroom Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park y ...
From $214 per night (USD)
VRBO
From $255 per night (USD)
Expedia
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treat yourself to the best while in Annapolis! Gorgeous 1500 sq. ft. custom designed waterfront apartment that takes fu ...
From $255 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $444 per night (USD)
VRBO
From $727 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $727 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Want to get away? Staying with us. Very relaxing.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our tastefully appointed cottages . Peaceful and tranquil, yet close to shops and restaurants, this property is perfect ...
From $210 per night (USD)
VRBO
From $543 per night (USD)
Expedia
Tranquil Waterfront Retreat w Stunning Views of the Chesapeake Bay and Bridge with Fenced-In Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat ...
From $543 per night (USD)
Expedia
$Eastport Cottage .5 mi from Downtown Annapolis\n\n$
From $446 per night (USD)
VRBO
Eastport Cottage .5 mi from Downtown Annapolis\n\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, t ...
From $446 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular vi ...
From $270 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Walk to USNA, Main St w Parking Historic Wisteria
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the ...
From $534 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $142 per night (USD)
Expedia
$Stay \Around the corner\ from Annapolis hot spots with new King bed, fenced-in yard and parking$
From $546 per night (USD)
VRBO
Stay \"Around the corner\" from Annapolis hot spots with new King bed, fenced-in yard and parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $546 per night (USD)
VRBO
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Expedia
A Delight on Dean
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sitting on a quiet, tree lined street, this home enjoys being located in the sought after neighborhood of Murray Hill. ...
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Expedia
From $737 per night (USD)
VRBO
Waterfront Cheerful 6 BR Home with Private Pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to this brand-new relaxing home with a private pier by the water for your getaway. It is perfect for vacations, ...
From $737 per night (USD)
VRBO
From $441 per night (USD)
Expedia
Walkable Eastport Home with Firepit, Porch & Fenced-in Yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Welcome to your home away from home in the heart of the Maritime Republic of Eastport—a vibrant, walkable neighborhood j ...
From $441 per night (USD)
Expedia
$\Dreams upon Weems\ Waterfront Cottage on Weems Creek in Annapolis$
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VRBO
\"Dreams upon Weems\" Waterfront Cottage on Weems Creek in Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Waterfront Home on Weems Creek in Annapolis with private water access for paddleboarding, kayaking, boating. Waterfro ...
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VRBO
From $495 per night (USD)
Expedia
Waterfront Oasis of Annapolis Star
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. S ...
From $495 per night (USD)
Expedia
From $186 per night (USD)
VRBO
New Loft w/South River view from treehouse deck!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that h ...
From $186 per night (USD)
VRBO
From $129 per night (USD)
Expedia
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore the best of Maryland and book a stay at this cozy 1-bed, 1-bath vacation rental home in Lothian! Nestled on a fa ...
From $129 per night (USD)
Expedia
From $438 per night (USD)
VRBO
Available for CW 2025 Family and Pet-friendly Edgewater cottage with hot tub in waterfront community
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Still available for Commissioning Week 2025! Welcome to this charming cottage located in a water-privileged community i ...
From $438 per night (USD)
VRBO
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Expedia
Beautiful, clean and Peaceful surrounded by parks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
There is a room to rent in a three level floor beautiful townhome . The bedrooms are on the third floor with a full bat ...
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Expedia
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VRBO
Vacation house near Downtown Annapolis
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Enjoy a weekend away in a secluded house in a lovely neighborhood right outside Annapolis. Our house is set back from th ...
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VRBO
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Expedia
Cute, cozy rancher close to down town Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
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Expedia
From $1039 per night (USD)
VRBO
Parking for days at the unique Deep in the Heart of Annapolis with large private deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $1039 per night (USD)
VRBO
Click For Pricing
Expedia
New Listing! Walk to USNA/Capitol/Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
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Expedia
From $630 per night (USD)
VRBO
Nice 5 BDR / 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Business, Govt. or family trip? Riviera Beach welcomes you to this lovely, elegant, well-lit and sanitized 5 BD/3 BATH h ...
From $630 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Downtown Annapolis Condo w/ Free Parking + Coffee
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $264 per night (USD)
Expedia
From $988 per night (USD)
VRBO
WATERFRONT Historic Home on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $988 per night (USD)
VRBO
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Expedia
Annapolis House
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
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Expedia
From $418 per night (USD)
VRBO
Harbor Breezes at Herrington Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $418 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $428 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Stylish Midcentury Ranch Home Just 1.5 Miles from Navy Stadium One-Level Living
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Stylish Midcentury Ranch Just 1.5 Miles from Navy Stadium! This beautifully renovated 4BR/2BA home is perfectly located ...
From $550 per night (USD)
VRBO
From $481 per night (USD)
Expedia
💥Your Annapolis Retreat near the beach and downtown💥
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Welcome to our recently renovated retreat in Annapolis. The place is located minutes from downtown, in the neighborhood ...
From $481 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located on Meridith Creek, which flows out to Whitehall and Chesapeake Bays, this charming vacation rental features a la ...
From $377 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Spectacular Location: State Circle Apartment
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $417 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Deluxe Basement Guest Suite w/ Luxury Amenities Minutes From BWI/Annapolis/DC
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to a luxurious retreat in Odenton. Boasting a stylish 2-bed design, stainless steel appliances, a rainfall shower ...
From $182 per night (USD)
VRBO
From $631 per night (USD)
Expedia
Eastport Historic Firehouse with Parking, Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Inquire about discounted extended stays! This is a unique home like none other in downtown Annapolis. Originally the Ea ...
From $631 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Annapolis Condominium in the heart of the historic center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $357 per night (USD)
VRBO
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Expedia
Chic Condo w/ Balcony in the Heart of Annapolis!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
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Expedia
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VRBO
Historic Annapolis Home Convenient to Downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For Pricing
VRBO
From $387 per night (USD)
Expedia
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A quiet, seaside escape awaits at this Shady Side vacation rental, hosting 3 bedrooms, 2 baths, at-home comforts and acc ...
From $387 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Annapolis Downtown Entire Townhome 3 bed 6 guests
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $413 per night (USD)
VRBO
From $1210 per night (USD)
Expedia
Parking at Randall House Across from USNA Gate 1
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1210 per night (USD)
Expedia
From $1074 per night (USD)
VRBO
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Spacious custom home - Perfect for Naval Academy families and long visits to Annapolis Enjoy your stay in this expansive ...
From $1074 per night (USD)
VRBO
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Expedia
5 BDRM across from the USNA Stadium
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
Click For Pricing
Expedia
From $1101 per night (USD)
VRBO
Private Pier Waterfront Jolly Roger mins to DTA
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $1101 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep ...
From $629 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $450 per night (USD)
VRBO
From $514 per night (USD)
Expedia
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from ...
From $514 per night (USD)
Expedia
From $829 per night (USD)
VRBO
1 Block to USNA at beautifully renovated Historic Chapel Views with back patio and off-site parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $829 per night (USD)
VRBO
From $727 per night (USD)
Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $727 per night (USD)
Expedia
From $664 per night (USD)
VRBO
Private Patio at Charming Hanover House Across from USNA Gate 3
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $664 per night (USD)
VRBO
From $206 per night (USD)
Expedia
Tranquility Awaits
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and twin. Full kitchen, laundry, dedi ...
From $206 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Bay View Studio Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $314 per night (USD)
VRBO
From $1165 per night (USD)
Expedia
Quiet home with large yard, close to Navy Bridge.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $1165 per night (USD)
Expedia
From $397 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $397 per night (USD)
VRBO
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Expedia
Studio, water community, private entrance, paver patio, off street parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Cozy studio, water access community with oversized windows facing large fenced yard with private paver patio, private en ...
Click For Pricing
Expedia
From $886 per night (USD)
VRBO
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $886 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Water Views - Close to Downtown Annapolis
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $541 per night (USD)
Expedia
From $552 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $552 per night (USD)
VRBO
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Expedia
Near BWI Airport! Free Breakfast + Pool + Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1-bedroom condo in Baltimore, Maryland is a comfortable and affordable accommodation perfect for families, groups a ...
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Expedia
From $239 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $239 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $571 per night (USD)
Expedia
From $601 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 $601 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Charming Charles Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $429 per night (USD)
Expedia
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VRBO
Pasadena Hideaway w/ Game Room & Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
From hosting afternoon picnics to making memories in the game room, this Pasadena vacation rental has everything you nee ...
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VRBO
From $302 per night (USD)
Expedia
Glen Burnie Vacation Rental w/ Private Deck!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Discover the best of the East Coast from this spacious 3-bed, 4-bath vacation rental in Glen Burnie. Located just a shor ...
From $302 per night (USD)
Expedia
From $930 per night (USD)
VRBO
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $930 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
Six bedroom 2020 Fountaine Pajot catamaran
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Beautiful 6 bedroom 6 bathroom catamaran just miles from downtown Annapolis on the South River from June to November. Sa ...
From $1181 per night (USD)
Expedia
From $2793 per night (USD)
VRBO
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Why rent a hotel when you can be in a Floatel on a Fountaine Pajot Saba luxurious 50 foot catamaran six Cabin six head l ...
From $2793 per night (USD)
VRBO
$Waterfront 5 Bedroom Near BWI\/Annapolis\/Baltimore$
From $1090 per night (USD)
Expedia
Waterfront 5 Bedroom Near BWI\/Annapolis\/Baltimore
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Summary: Escape to paradise in this stunning 5-bedroom private waterfront oasis, only 20 minutes from BWI airport, US Na ...
From $1090 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
| OVERVIEW | Welcome aboard FLOHOM 3 | Bung-a-flo, a Bohemian-inspired floating tiny home docked at the scenic Ferry P ...
From $525 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $495 per night (USD)
Expedia
Click For Pricing
VRBO
1 bedroom 1 bath 10-15 minutes to Maryland live Casino . KITCHEN.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
15 minutes Maryland live Casino and BWI airport and 15-20 minutes to Baltimore . 20-25 min Annapolis , Walmart , Planet ...
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VRBO
From $422 per night (USD)
Expedia
13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Furnished Deck | Fenced Backyard | In-Unit Laundry | 25 Mi to Washington, D.C. Book this Crofton home-away-from-home! W ...
From $422 per night (USD)
Expedia
From $288 per night (USD)
VRBO
SYR Properties
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
About this space We aim to provide guests with a clean, comfortable, and safe "home away from home." Our location is con ...
From $288 per night (USD)
VRBO
Click For Pricing
Expedia
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
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Expedia

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