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$Cozy 2br home w\/ parking in downtown Annapolis$
From $298 per night (USD)
VRBO
Cozy 2br home w\/ parking in downtown Annapolis
Bedrooms:
2
Bathrooms:
3
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 $298 per night (USD)
VRBO
$Nice retreat apartment\/private patio, min. away from USNA & Downtown Annapolis$
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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 ...
Click For Pricing
Expedia
From $271 per night (USD)
VRBO
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
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 $271 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Adorable waterside cottage with pool Beach community
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $325 per night (USD)
Expedia
From $184 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 $184 per night (USD)
VRBO
From $466 per night (USD)
Expedia
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $466 per night (USD)
Expedia
$Jode's Retreat \Your home away from home$
From $231 per night (USD)
VRBO
Jode's Retreat \"Your home away from home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Clear the calendar for an easy-going getaway at "Jode's Retreat"; ideal for USNA events (a 2-minute drive to the stadium ...
From $231 per night (USD)
VRBO
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Expedia
Waterfront
Bedrooms:
6
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 $426 per night (USD)
VRBO
Stay close to USNA Stadium with screened-in porch and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Visit the magic of Annapolis during the Holiday Season Welcome to this charming Cape Cod on half an acre right outside d ...
From $426 per night (USD)
VRBO
From $357 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 $357 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $145 per night (USD)
Expedia
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)
Expedia
From $409 per night (USD)
VRBO
Perfect location for Inauguration activities. Contact for price reduction.
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 $409 per night (USD)
VRBO
From $242 per night (USD)
Expedia
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 $242 per night (USD)
Expedia
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VRBO
Perfect historic home + Peloton, walk to downtown Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely historic home within walking distance from downtown (1 mile from Church Circle) & Navy stadium (5 blocks), hardwo ...
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VRBO
From $152 per night (USD)
Expedia
Private Apartment - Minutes to USNA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Entire home You’ll have the apartment to yourself. Great location 100% of recent guests gave the location a 5-star ratin ...
From $152 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $313 per night (USD)
VRBO
$Cute Bay Home\/Fantastic View and Sandy Beach$
From $351 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 $351 per night (USD)
Expedia
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VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Visit the magic of Annapolis during the Holiday Season The gorgeous Downtown Annapolis home was meticulously remodeled f ...
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VRBO
From $836 per night (USD)
Expedia
Available for CW 2025 Historic home steps to Main St w Capital views, free off-site parking, patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Experience Historic Annapolis in Comfort and Style This charming ...
From $836 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $618 per night (USD)
VRBO
$Retreat on Sage Brush Court (Basement Suite w\/private entrance)$
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Expedia
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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Expedia
From $716 per night (USD)
VRBO
A luxurious spa-like retreat near the Chesapeake Bay
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Treat yourself to luxury around every corner in this stunning home appointed with two spacious Primary Bedroom ensuites ...
From $716 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Welcome to this gorgeous fully-renovated home, restored to a new ...
From $521 per night (USD)
Expedia
Click For Pricing
VRBO
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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VRBO
From $241 per night (USD)
Expedia
Cozy 1st Floor King George one bedroom apartment right across from USNA
Bedrooms:
1
Bathrooms:
2
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 $241 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Luxury Townhouse, 3 BR, 2.5 bath near Fort Meade
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Large 3 bedrom Townhouse, open kitchen, large airy rooms. Upgraded bathrooms and kitchen. Walking distance to Fort Meade ...
From $301 per night (USD)
VRBO
From $333 per night (USD)
Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's l ...
From $333 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Charming Downtown 3rd Floor 1 Bedroom Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park y ...
From $201 per night (USD)
VRBO
From $224 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 $224 per night (USD)
Expedia
From $342 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 $342 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $432 per night (USD)
Expedia
From $607 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $607 per night (USD)
VRBO
From $210 per night (USD)
Expedia
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)
Expedia
From $523 per night (USD)
VRBO
Available for CW 2025 1 level water-privileged home with private deck, screened porch and backyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Escape to a tranqui ...
From $523 per night (USD)
VRBO
$Eastport Cottage .5 mi from Downtown Annapolis\n\nNIGHTLY PRICE REDUCTION!!!!!!$
From $388 per night (USD)
Expedia
Eastport Cottage .5 mi from Downtown Annapolis\n\nNIGHTLY PRICE REDUCTION!!!!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
NIGHTLY PRICE REDUCTION AS OF 11.04.2024! Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Ch ...
From $388 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular vi ...
From $250 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Walk to USNA and Main Street with Parking at Historic Wisteria
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths ...
From $528 per night (USD)
Expedia
From $355 per night (USD)
VRBO
WATERFRONT| 4BR| 1st Floor Master|Family Ready|BWI
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Recently remodeled! Waterfront property tucked away, but close to civilization • Deck off the main level to enjoy the v ...
From $355 per night (USD)
VRBO
From $211 per night (USD)
VRBO
*Chesapeake Bayside Bungalow*
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Amazing three bedroom two bath home only 20 miles from Annapolis! You will be a quick walk away from the Chesapeake Bay ...
From $211 per night (USD)
VRBO
From $654 per night (USD)
VRBO
Bennett House (entire):Haven in Historic Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with 3 ...
From $654 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Cozy place close to the city dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis; where history and nature coincide! You will feel right at home in this confortable 1 bedroom 1 bat ...
From $125 per night (USD)
Expedia
$Still available for CW 2025! \Around the corner\ from everything w fenced-in yard and parking$
From $509 per night (USD)
VRBO
Still available for CW 2025! \"Around the corner\" from everything w fenced-in yard and parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Welcome to this cha ...
From $509 per night (USD)
VRBO
Click For Pricing
Expedia
A Delight on Dean
Bedrooms:
3
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 $386 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
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Welcome to this cha ...
From $386 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Steps to the marinas with Private back deck, yard and Easy parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Visit the magic of Annapolis during the Holiday Season This professionally-decorated and furnished 2 bedroom, 1.5 bath i ...
From $604 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 ...
Click For Pricing
VRBO
From $441 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 $441 per night (USD)
Expedia
$New Loft w\/South River view from treehouse deck!$
From $176 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 $176 per night (USD)
VRBO
$Secluded Lothian Farmhouse on 45 Acres w\/ Fire Pit$
From $116 per night (USD)
Expedia
Secluded Lothian Farmhouse on 45 Acres w\/ Fire Pit
Bedrooms:
1
Bathrooms:
2
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 $116 per night (USD)
Expedia
From $645 per night (USD)
VRBO
Waterfront Cheerful 6 BR Home with Private Pier
Bedrooms:
6
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 $645 per night (USD)
VRBO
Click For Pricing
Expedia
Vacation house near Downtown Annapolis
Bedrooms:
5
Bathrooms:
8
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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Expedia
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VRBO
Beautiful, clean and Peaceful surrounded by parks
Bedrooms:
2
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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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 ...
Click For Pricing
Expedia
From $146 per night (USD)
VRBO
1 Bedroom Basement Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Beautiful one Bedroom Basement apartment located in the beautiful Seven Oaks Community, Odenton, Maryland. - Walking d ...
From $146 per night (USD)
VRBO
From $1037 per night (USD)
Expedia
Deep in the Heart of Annapolis; Parking for days!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Visit the magic of Annapolis during the Holiday Season Welcome to this gorgeous Texas-themed downtown Annapolis home. Ev ...
From $1037 per night (USD)
Expedia
$New Listing! Walk to USNA\/Capitol\/Downtown$
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VRBO
New Listing! Walk to USNA\/Capitol\/Downtown
Bedrooms:
3
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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VRBO
$Nice 5 BDR \/ 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance$
From $486 per night (USD)
Expedia
Nice 5 BDR \/ 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance
Bedrooms:
3
Bathrooms:
6
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 $486 per night (USD)
Expedia
$Downtown Annapolis Condo w\/ Free Parking + Coffee$
From $311 per night (USD)
VRBO
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 $311 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Renovated historic apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $379 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Renovated historic apartment
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $418 per night (USD)
VRBO
From $837 per night (USD)
Expedia
WATERFRONT Historic Home on the Chesapeake Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $837 per night (USD)
Expedia
Click For Pricing
VRBO
Annapolis House
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For Pricing
VRBO
From $408 per night (USD)
Expedia
Harbor Breezes at Herrington Harbor
Bedrooms:
3
Bathrooms:
5
Sleeps:
7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $408 per night (USD)
Expedia
From $399 per night (USD)
VRBO
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 $399 per night (USD)
VRBO
$Charming 4BR 2BA w\/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT$
From $367 per night (USD)
Expedia
Charming 4BR 2BA w\/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Come stay at this fully updated cozy 4-bedroom 2-bathroom home. Conveniently located with a .6 mile walk to the Naval Ac ...
From $367 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Visit the magic of Annapolis during the Holiday Season Welcome to this beautifully renovated midcentury ranch home, perf ...
From $577 per night (USD)
VRBO
From $302 per night (USD)
Expedia
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 $302 per night (USD)
Expedia
From $489 per night (USD)
VRBO
💥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 $489 per night (USD)
VRBO
From $375 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 $375 per night (USD)
Expedia
$Deluxe Basement Guest Suite w\/ Luxury Amenities Minutes From BWI\/Annapolis\/DC$
From $174 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 $174 per night (USD)
VRBO
From $587 per night (USD)
Expedia
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Inquire about discounted extended stays! This is a unique home l ...
From $587 per night (USD)
Expedia
From $601 per night (USD)
VRBO
Available for CW 2025 Multiple family spaces both inside and out 13 mins to USNA
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! From the moment you ...
From $601 per night (USD)
VRBO
From $341 per night (USD)
Expedia
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 $341 per night (USD)
Expedia
$Chic Condo w\/ Balcony in the Heart of Annapolis!$
From $362 per night (USD)
VRBO
Chic Condo w\/ Balcony in the Heart of Annapolis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
From $362 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $256 per night (USD)
VRBO
Private coastal Guest Suite with pool. Minutes from Downtown Annapolis and USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immaculately designed separate guest suite/apartment with private bath, Serta Queen bed and luxury linens. Guests have t ...
From $256 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
A quiet, seaside escape awaits at this Shady Side vacation rental, hosting 3 bedrooms, 2 baths, at-home comforts and acc ...
From $292 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Annapolis Downtown Entire Townhome 3 bed 6 guests
Bedrooms:
2
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 $410 per night (USD)
VRBO
From $925 per night (USD)
Expedia
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Visit the magic of Annapolis during the Holiday Season The Randall House is an historic gem in the heart of Downtown Ann ...
From $925 per night (USD)
Expedia
From $744 per night (USD)
VRBO
Available for CW 2025 Sprawling custom home on a private Cul De Sac with gaming sports bar
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Visit the magic of Annapolis during the Holiday Season Spacious large home - Perfect for Naval Academy families and long ...
From $744 per night (USD)
VRBO
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Expedia
5 BDRM across from the USNA Stadium
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
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Expedia
From $699 per night (USD)
VRBO
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our quiet 3 bed 2.5 bath home is the perfect Annapolis getaway! On a dead end road. A quick walk to the best downtown r ...
From $699 per night (USD)
VRBO
From $887 per night (USD)
Expedia
Available for CW 2025 Waterfront dog-friendly Private Pier, Game Room at Jolly Roger
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Arrive by car or bo ...
From $887 per night (USD)
Expedia
$Annapolis Cozy Beachfront\/Waterfront w\/Chesapeake Bay Bridge view$
From $596 per night (USD)
VRBO
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 $596 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $426 per night (USD)
Expedia
$Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis \/USNA$
From $439 per night (USD)
VRBO
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 $439 per night (USD)
VRBO
From $911 per night (USD)
Expedia
1 Block to USNA with Chapel Views big back patio and off-site parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Visit the magic of Annapolis during the Holiday Season When the owners decided to find their Annapolis home base, they k ...
From $911 per night (USD)
Expedia
From $716 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $716 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Hanover House across from USNA Gate 3 with private back patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season The fully-renovated 1800 historic home is just steps from USNA’s ...
From $522 per night (USD)
Expedia
From $142 per night (USD)
VRBO
Tranquility Awaits
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and single. Full kitchen, laundry, de ...
From $142 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Bay View Studio Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $264 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Water Views- Boating Fishing -Annapolis-DC-Chesapeake Bay-Kayaking-Paddle Boards
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Water Views from almost every room, great location walking distance to several great restaurants. Prime location in the ...
From $618 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Quiet home with large yard, close to Navy Bridge.
Bedrooms:
3
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 $455 per night (USD)
Expedia
From $377 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 $377 per night (USD)
VRBO
Click For Pricing
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 $780 per night (USD)
VRBO
Still available for CW 2025 Steps to Gate 1 at Naval-Academy-themed home, custom bar, onsite parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Welcome to Modern E ...
From $780 per night (USD)
VRBO
From $550 per night (USD)
Expedia
Water Views - Close to Downtown Annapolis
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $550 per night (USD)
Expedia
From $476 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $476 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia

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