Severn River, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Severn River, Maryland on RentalSaver.com!

Severn River Rentals

From $683 per night (USD)
VRBO
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $683 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor ...
From $477 per night (USD)
Expedia
$Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n$
From $328 per night (USD)
VRBO
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $328 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Downtown Pinkney House w/Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $377 per night (USD)
Expedia
From $955 per night (USD)
VRBO
Brand New Spacious Luxury Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $955 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $300 per night (USD)
Expedia
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VRBO
Gorgeous House in the Heart of Annapolis, Walk to Everything!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
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VRBO
From $931 per night (USD)
Expedia
Luxury Home with Pool for 20
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Vacation in luxury with 20 of your closest friends and family. This 5000+ square foot home with a pool sits at the end o ...
From $931 per night (USD)
Expedia
From $830 per night (USD)
VRBO
Main Street 4BR Gem – Steps to Waterfront, USNA, Shops & Dining
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - PLEASE NOTE: THIS PROPERTY IS MANAGED BY AN ...
From $830 per night (USD)
VRBO
From $792 per night (USD)
Expedia
Townhome steps from Main St. with private backyard patio & parking
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
From $792 per night (USD)
Expedia
Click For Pricing
VRBO
Waterviews, steps to restaurants and downtown from First Mate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Still available for Commissioning Week 2025! Stunning 4 Bedroom / 3.5 Bath Home in Eastport with Water Views and Expans ...
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VRBO
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Expedia
Annapolis Home Near Beach & Quiet Waters Park!
Bedrooms:
2
Bathrooms:
4
Sleeps:
13
2,552 Sq Ft | Dog Friendly w/ Fee | Wood-Burning Fireplace | 4 Mi to Downtown Annapolis Nestled just 2 miles from the C ...
Click For Pricing
Expedia
From $362 per night (USD)
VRBO
Cozy Cottage with Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and e ...
From $362 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Steps to Marinas & Shops w Parking in Eastport
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis This beautiful home is located in ...
From $577 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Mins to DTA - King Beds - Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $621 per night (USD)
VRBO
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Expedia
Downtown Nights on the Water - Classic Cruiser Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the heart of Annapolis, this 35-foot Formula boat offers an unforgettable overnight stay. With a small kitche ...
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Expedia
From $730 per night (USD)
VRBO
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to The Yellow Annapolis Cottage: A Chesapeake Getaway with Stunning Bay Views Welcome to our Bay Ridge Yellow C ...
From $730 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Less than 1 mile to Navy Stadium, Fenced-in Yard and Dog-Friendly Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
A new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect ...
From $658 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Stay in the Heart of Annapolis on King George Street Steps to USNA Gate 1 & Main Street
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $529 per night (USD)
VRBO
From $1334 per night (USD)
Expedia
Premier Retreat: Private Pool, Spa, Fireplace & Spacious Deck-Entertainers Dream
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Spacious Private Getaway – Pool, Spa, Fireplace & Outdoor Entertainment! Welcome to your perfect retreat—a 5-bedroom, 4 ...
From $1334 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Take it easy at this unique and tranquil getaway in historic Eastport
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of spa ...
From $415 per night (USD)
VRBO
From $85 per night (USD)
Expedia
Charming townhome with AC and WiFi in delightful Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property is near naval Acedemy and downtown and harbourit is connected by bus route 70 and green bus and free downtown s ...
From $85 per night (USD)
Expedia
From $693 per night (USD)
VRBO
New Home w Luxe King Suite, Porch Vibes & Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New Beautiful Home in Downtown Annapolis’ Murray Hill Walk to Downtown with Gourmet Kitchen Welcome to your home-away-f ...
From $693 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Charming 3-bedroom house in Annapolis Eastport! Beautiful fully furnished home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful fully furnished 3 bedroom, 2 bath home, available for short term rental in Eastport Annapolis! 4 minutes uber ...
From $415 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Charming 3-bedroom house with WiFi, AC in awesome Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a wonderful 3-bedroom house in Annapolis. This cozy retreat features 2 full beds and 1 bunk bed, perfect for a ...
From $523 per night (USD)
VRBO
From $796 per night (USD)
Expedia
Stunning 4 BR Home - Walking Distance to Stadium
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: This charming 4 BR home is conveniently located in Annapolis' Germantown neighborhood; within walking distance ...
From $796 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Beautiful Historic Flat next to City Dock + USNA
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis ...
From $402 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $552 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Water view Oasis renovated 3 bedrooms, 2.5 bath &hot tub conveniently in Arnold!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Arnold like a local in this 3-bedroom house. This peaceful retreat offers 1 king bed and 3 queen beds, perfec ...
From $492 per night (USD)
VRBO
From $776 per night (USD)
Expedia
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Mar ...
From $776 per night (USD)
Expedia
From $815 per night (USD)
VRBO
Stay in the Heart of Historic Annapolis in this unique two-unit home with parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportun ...
From $815 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Pet-Friendly & Spacious Home in Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Spacious 4BR/2.5BA home roughly 10 mins from Downtown Annapolis - close to the action, yet tucked in a quiet ne ...
From $717 per night (USD)
VRBO
From $557 per night (USD)
VRBO
Modern Styled Home in Historic Annapolis Eastport Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $557 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Adorable 1 bedroom apartment in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the att ...
From $275 per night (USD)
Expedia
From $373 per night (USD)
VRBO
2 Bedroom Renovated Condo in Downtown Annapolis
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Newly renovated 2 bedroom apartment in downtown Annapolis. Steps from Main Street and all that Annapolis has to ...
From $373 per night (USD)
VRBO
From $616 per night (USD)
VRBO
Downtown Annapolis Gem: 3BR/2BA
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $616 per night (USD)
VRBO
From $238 per night (USD)
VRBO
1 room with additional amazing sunroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
Summary: Enjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the a ...
From $238 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Lovely 1 bedroom apartment in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to off ...
From $234 per night (USD)
Expedia
From $655 per night (USD)
VRBO
Private 4-bedroom house in Annapolis, great location!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Your home away from home in Annapolis with 4 bedrooms. Under 2 miles to the Naval Academy! This spacious home is located ...
From $655 per night (USD)
VRBO
From $943 per night (USD)
VRBO
Magnolia Harbor Retreat - 4 BR/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
RENT-001081-2024 - HOME OWNER HAS A PET SO THIS SHOULD BE TAKEN INTO CONSIDERATION WHEN BOOKING BY ANY GUEST WITH ALLERG ...
From $943 per night (USD)
VRBO
From $976 per night (USD)
VRBO
Stunning Home Nestled on the Peninsula of Eastport
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $976 per night (USD)
VRBO
From $640 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $640 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $574 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Historic Downtown Charmer, Water Views and Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $425 per night (USD)
VRBO
From $618 per night (USD)
VRBO
Nautical Feel to This Beautiful Eastport Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
From the minute you walk in the door, you will feel the warmth and charm this home offers. Located on the Eastport si ...
From $618 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Eastport Haven House
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best r ...
From $547 per night (USD)
VRBO
From $831 per night (USD)
VRBO
Charming Annapolis Victorian
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $831 per night (USD)
VRBO
From $3256 per night (USD)
VRBO
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
This home has everything for enjoying waterfront and poolside living, while also being very convenient to major tourist ...
From $3256 per night (USD)
VRBO
From $367 per night (USD)
VRBO
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Vacations are meant to be carefree! Let the chimes from the Naval Academy chapel start your day. Stroll along our famed ...
From $367 per night (USD)
VRBO
From $598 per night (USD)
VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. They will be given on request. Rates a ...
From $598 per night (USD)
VRBO
From $171 per night (USD)
VRBO
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Hist ...
From $171 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Perfect location for USNA Commissioning Week
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Begin your mornings with wraparound views from the queen bed or coffee on the screened porch, with the same water views ...
From $446 per night (USD)
Expedia
$Annapolis waterfront \tiny house\ in garden setting$
From $171 per night (USD)
VRBO
Annapolis waterfront \"tiny house\" in garden setting
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This " Carriage House" is a tiny jewel box, space efficient as a boat and comfortable as a modern home. Located in t ...
From $171 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $226 per night (USD)
VRBO
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VRBO
Wooded retreat minutes from Downtown Annapolis!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
Click For Pricing
VRBO
From $747 per night (USD)
VRBO
92 Five Star Reviews & located in a quiet neighborhood in the City of Annapolis!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This is one of the most charming houses in Murray Hill! Located on a dead end street, this brick colonial with a slate r ...
From $747 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. I ...
From $648 per night (USD)
VRBO
From $722 per night (USD)
VRBO
Beautiful Waterfront Townhome In Historic Annapolis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $722 per night (USD)
VRBO
$Historic District\Crab Cakes and Football\$
From $483 per night (USD)
VRBO
Historic District\"Crab Cakes and Football\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $483 per night (USD)
VRBO
From $2075 per night (USD)
VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and t ...
From $2075 per night (USD)
VRBO
From $653 per night (USD)
VRBO
Beautifully Renovated Historic District Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $653 per night (USD)
VRBO
From $831 per night (USD)
Expedia
Charming Historic Annapolis Home With Two Off-street Parking Places!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $831 per night (USD)
Expedia
From $773 per night (USD)
VRBO
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
CHARMING FOUR BEDROOM WATERFRONT COTTAGE ON SCENIC SEVERN RIVER WITH STUNNING VIEWS -- RARE CLOSE-IN LOCATION - JUST MI ...
From $773 per night (USD)
VRBO
From $1389 per night (USD)
VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Spacious historic Annapolis home, located mere steps to the Naval Academy and St. John's College. Two blocks from the St ...
From $1389 per night (USD)
VRBO
From $1522 per night (USD)
VRBO
Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
STR21-144966 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1522 per night (USD)
VRBO
From $441 per night (USD)
VRBO
Perfect spot for a Weekend Getaway!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city ga ...
From $441 per night (USD)
VRBO
From $1440 per night (USD)
VRBO
Waterfront Gem! Resort-like home with big windows and truly breathtaking water views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1440 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Beautiful Historic Home With Great Location!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The "Philip Clayton House" (Annapolis license STR21-144988) is a fully up-dated, historic home in the Federal style dat ...
From $539 per night (USD)
Expedia
From $96 per night (USD)
VRBO
Amazing Bright Big Window Loft Heart of Eastport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful furnished or semi furnished loft apartment in Eastport. Views of the Severn river, naval academy , Sailboat’s, ...
From $96 per night (USD)
VRBO
From $611 per night (USD)
VRBO
Spacious, contemporary, wooded home in Epping Forest on the Severn River
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Beautiful home in Epping Forest with large granite counters and stainless kitchen with open floor plan for family gather ...
From $611 per night (USD)
VRBO
$Beautifully updated Annapolis Historic District rowhome w\/ parking and rooftop deck$
From $734 per night (USD)
VRBO
Beautifully updated Annapolis Historic District rowhome w\/ parking and rooftop deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
STR21-14492 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $734 per night (USD)
VRBO
From $1487 per night (USD)
Expedia
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy the best of Eastport and downtown Annapolis in this cute historic home. Home has three levels with space for 10-1 ...
From $1487 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Chesapeake living with a view of the Bay from the lovely outdoor dining area and screened in balcony off of the huge mas ...
From $808 per night (USD)
VRBO
From $1454 per night (USD)
VRBO
RARELY AVAILABLE FOR COMMISSIONING WEEK! Stunning colonial on a private 1.6 acre lot!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
STR00844 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1454 per night (USD)
VRBO
From $226 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment One B
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $226 per night (USD)
VRBO
From $1393 per night (USD)
VRBO
Beautiful home w/elevator going to every floor. This house is accessible to all.
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1393 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Delightful little Historic District gem - for the antique lover and history buff.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR21-144963 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $531 per night (USD)
VRBO
From $936 per night (USD)
VRBO
One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $936 per night (USD)
VRBO
From $830 per night (USD)
VRBO
Elegant yet modern historic home in the heart of downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $830 per night (USD)
VRBO
From $570 per night (USD)
VRBO
DOWNTOWN ANNAPOLIS DREAMHOME AWAITS!!! 3 BR charming home sits in the heart of Annapolis within walking distance to all major points of interest AND a Rooftop Deck!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR-144253 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $570 per night (USD)
VRBO
From $1376 per night (USD)
VRBO
Water view from every window - Located at the point where the deep water of Saltworks Creek meets the Severn River.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR50082- THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1376 per night (USD)
VRBO
From $959 per night (USD)
VRBO
4 BR/3BA home in the heart of Historic Downtown Annapolis. 1 1/2 blocks from the Naval Academy
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-141783 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $959 per night (USD)
VRBO
From $759 per night (USD)
VRBO
Location=AMAZING! Garage Parking for 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $759 per night (USD)
VRBO
From $913 per night (USD)
VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $913 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $221 per night (USD)
VRBO
From $495 per night (USD)
VRBO
Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $495 per night (USD)
VRBO
From $1276 per night (USD)
VRBO
RARELY AVAILABLE -Waterfront Home – Walkable to USNA | 2025/2026 Event Weeks Available
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it ...
From $1276 per night (USD)
VRBO
From $1186 per night (USD)
VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1186 per night (USD)
VRBO
From $940 per night (USD)
VRBO
Clean, Spacious Family House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and p ...
From $940 per night (USD)
VRBO
From $733 per night (USD)
VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $733 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Charming cottage with parking. Easy walk to downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $376 per night (USD)
VRBO
From $499 per night (USD)
VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill ...
From $499 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Charming Renovated Historic Home Downtown wparking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $410 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Welcome Aboard the Kathleen Marie!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annap ...
From $403 per night (USD)
VRBO
From $369 per night (USD)
VRBO
Fleet St Retreat in Downtown- Great Location !
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
We welcome you to our brand new renovation on Fleet Street . Purchased in 2016 this house was taken down to the studs so ...
From $369 per night (USD)
VRBO
From $392 per night (USD)
VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that l ...
From $392 per night (USD)
VRBO
From $2907 per night (USD)
VRBO
Nantucket on the Chesapeake Heated Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2907 per night (USD)
VRBO
Click For Pricing
Expedia
Quiet & Relaxing Waterfront Home Near Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Quiet and Relaxing Waterfront home 5 minutes from Downtown Annapolis. Ideal for Business stays, Relocation Home, Get Tog ...
Click For Pricing
Expedia
From $646 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $646 per night (USD)
VRBO
From $580 per night (USD)
Expedia
All-stop. Rental Midships.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $580 per night (USD)
Expedia

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