Anne Arundel Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anne Arundel Area, Maryland on RentalSaver.com!

Anne Arundel Area Rentals

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From $588 per night (USD)
VRBO
Great Entertaining Spot for any Occassion!
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $588 per night (USD)
VRBO
From $244 per night (USD)
VRBO
New Bungalow with view of South River!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern bungalow that ha ...
From $244 per night (USD)
VRBO
From $640 per night (USD)
VRBO
Tastefully decorated fully-equipped Eastport Annapolis house with water views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our renovated 3 story house is located on the peninsula of Eastport, Annapolis. We are across the street from a small m ...
From $640 per night (USD)
VRBO
From $443 per night (USD)
Expedia
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 $443 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
The Firefly Cottage (cute as the bug!) in beautiful Cape St. Claire. We customize each stay, a gift basket with wine or ...
From $297 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Waterfront With Relaxing Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The house has 2 master bedrooms on upper level. One of them has private deck and panoramic views. There is one bedroom ...
From $412 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Annapolis steps to Harbor and Naval Academy
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1s ...
From $236 per night (USD)
VRBO
From $335 per night (USD)
Expedia
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 $335 per night (USD)
Expedia
From $736 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 $736 per night (USD)
VRBO
From $808 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 $808 per night (USD)
Expedia
From $738 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 $738 per night (USD)
VRBO
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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 ...
Click For Pricing
Expedia
From $577 per night (USD)
VRBO
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Bedrooms:
3
Bathrooms:
5
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 $577 per night (USD)
VRBO
From $748 per night (USD)
Expedia
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 $748 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Our charming carriage house, nestled in privacy on 42 acres, offers a relaxing Adirondack-type getaway for up to 5 gues ...
From $318 per night (USD)
VRBO
From $972 per night (USD)
VRBO
102 5-star Reviews located inside the City of Annapolis in Murray Hill.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located on a dead end street, this charming brick colonial with a slate roof sits on a beautiful lot just 1/2 block from ...
From $972 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Waterfront Apartment with Fantastic Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We call this recently renovated luxury apartment Hale Kai, which is Hawaiian for 'Sea House.' It is fully furnished and ...
From $254 per night (USD)
VRBO
From $765 per night (USD)
VRBO
Lots free parking, hot tub, 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 $765 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $736 per night (USD)
VRBO
Ultraclean Family Waterfront Home Annapolis Area - 200+ Top Reviews!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Breathtaking views from our waterfront property ... 10 minutes outside Annapolis, Maryland. Light-filled and open floor ...
From $736 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New Outdoor Space for 2026! Enjoy sunrises on the newly built porch. A great space for morning coffee or to spend an ev ...
From $469 per night (USD)
VRBO
From $865 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 $865 per night (USD)
VRBO
From $1107 per night (USD)
VRBO
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Spacious 5-bedroom (4 full- and 2 half-baths) waterfront getaway built along the natural topography of Fairhaven Cliffs. ...
From $1107 per night (USD)
VRBO
From $930 per night (USD)
VRBO
Waterfront home in Annapolis MD with private pier
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Waterfront home, 2000 sq feet, in Annapolis, MD on Magothy River, overlooking Chesapeake Bay, Gibson Island with private ...
From $930 per night (USD)
VRBO
$Historic District\Crab Cakes and Football\$
From $600 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 $600 per night (USD)
VRBO
From $2295 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 $2295 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Pasadena, MD close to Annapolis/WDC/Baltimore
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Rest, relax in the color and light of the house, breathe and welcome the calm. 20 minutes to Annapolis and Baltimore, 15 ...
From $346 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $279 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 $279 per night (USD)
VRBO
From $580 per night (USD)
VRBO
4-Bedroom Eastport Haven + Walk to Downtown & USNA + Rare Multi-Car Parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your ultimate Annapolis getaway! Tucked into a quiet, private cul-de-sac in desirable Eastport, our home offe ...
From $580 per night (USD)
VRBO
From $176 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 $176 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready an ...
From $279 per night (USD)
Expedia
$Annapolis waterfront \tiny house\ in garden setting$
From $176 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 $176 per night (USD)
VRBO
From $394 per night (USD)
Expedia
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 $394 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Chesapeake Sparkles Sky-Lit Studio Flat + Solarium
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your party will have two lovely private spaces, connected by a door, on the second floor of the Chesapeake Paradise Hou ...
From $279 per night (USD)
VRBO
From $649 per night (USD)
VRBO
Gorgeous Annapolis Area Waterfront Home!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Beautiful views of the river as you enter this 5 bedroom waterfront home. Imagine watching boats from the screened-in po ...
From $649 per night (USD)
VRBO
From $1064 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 $1064 per night (USD)
VRBO
From $1986 per night (USD)
VRBO
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Bedrooms:
4
Bathrooms:
5
Sleeps:
18
This home has everything for enjoying waterfront and poolside living, while also being very convenient to major tourist ...
From $1986 per night (USD)
VRBO
From $427 per night (USD)
VRBO
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 $427 per night (USD)
VRBO
From $439 per night (USD)
Expedia
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 $439 per night (USD)
Expedia
From $259 per night (USD)
VRBO
National Historic home w/ Serene & Quiet Setting
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Originally founded in the 1600's, Abington Farm, a.k.a Abbington Manor & Stables, is a historic home and stables in Crow ...
From $259 per night (USD)
VRBO
From $640 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 $640 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Annapolis Bay House BOAT SHOW & USNA Families 2 Bedroom with Den sleeps 5
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Charming Bay Cottage just steps from a beautiful beach and the Chesapeake Bay, a short drive or walk to the crabbing an ...
From $393 per night (USD)
VRBO
From $553 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 $553 per night (USD)
VRBO
From $630 per night (USD)
VRBO
Historic Capital Views, w Free Off-Site Parking & Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Experience Historic Annapolis in Comfort and Style ...
From $630 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
In this lovely home in a quiet neighborhood in Cape St. Claire, Annapolis, MD, you are a short 12-minute car ride from t ...
From $609 per night (USD)
VRBO
From $1531 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 $1531 per night (USD)
VRBO
From $653 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this gorgeous fully-renovated home, res ...
From $653 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Chesapeake Bay single family home
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront ...
From $730 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $476 per night (USD)
VRBO
Waterfront cottage on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Live the Chesapeake life style in this 4 BR 2 bath home with a private dock on 150 ft of Back Creek waterfront. This hom ...
From $476 per night (USD)
VRBO
From $247 per night (USD)
Expedia
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)
Expedia
From $400 per night (USD)
VRBO
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 $400 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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 $241 per night (USD)
Expedia
From $398 per night (USD)
VRBO
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 $398 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Washington Baltimore Annapolis area home, great for re-lo or extended stay
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Nicely furnished, two story, 2745 sq ft. “colonial”, is located in quiet suburb of Baltimore and Annapolis. 45 minute ...
From $231 per night (USD)
VRBO
From $481 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 $481 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Million Dollar View of the Chesapeake Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
'Fredelig sted'(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine a ...
From $501 per night (USD)
Expedia
From $1010 per night (USD)
VRBO
Beautiful Downtown Annapolis Townhome!
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 $1010 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Historic Downtown House with Off Street Parking
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
From $426 per night (USD)
Expedia
From $351 per night (USD)
VRBO
The Yellow Cottage on Harness Creek
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The minute you step into our charming waterfront cottage you will feel right at home! Situated on Harness Creek, in a q ...
From $351 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
A perfect getaway spot, on a peninsula on the West River just across from Galesville. Houses on the point are mostly w ...
From $201 per night (USD)
VRBO
From $341 per night (USD)
VRBO
Nice clean townhome in the middle of everything mall, airport, DC, Baltimore ect
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
*Kingsize bed in master bedroom (nice sweet) * Beautiful view front and back *joint his and her bathroom *nice kitchen ...
From $341 per night (USD)
VRBO
From $632 per night (USD)
Expedia
Scenic Waterfront Retreat Mins to Annapolis w Panoramic Bay/Bridge Views & Fenced-In Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Relaxing Waterfront Retreat Near Annapolis – Pet F ...
From $632 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Annapolis Charm Waterfront Private Fishing Dock Pier Near Beach & Naval Academy
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier ...
From $549 per night (USD)
VRBO
From $1807 per night (USD)
Expedia
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Newly Renovated with larger bedrooms and 2 more bathrooms! Enjoy Annapolis with family & friends all year at this extrao ...
From $1807 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Eastport Cottage .5 mi from Downtown Annapolis
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 $599 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Walk to USNA, Main St w Parking Historic Wisteria
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis How many homes in Downtown Annapolis have 4 Bedroo ...
From $629 per night (USD)
Expedia
From $2824 per night (USD)
VRBO
Cool 1870's home anchored in the Historic District with modern amenities.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of t ...
From $2824 per night (USD)
VRBO
From $530 per night (USD)
Expedia
NEW 5 Bedroom Home with Pier by Water
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to this brand-new relaxing home with a pier by the water for your getaway. It is perfect for vacations, retreats ...
From $530 per night (USD)
Expedia
From $160 per night (USD)
VRBO
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 $160 per night (USD)
VRBO
$\Around the Corner\ from Eastport Hot Spots with Fenced-In Yard and Parking$
From $613 per night (USD)
Expedia
\"Around the Corner\" from Eastport Hot Spots with Fenced-In Yard and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Still available for Commissioning Week 2025! ...
From $613 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Renovated Apt In Historic Dist w/2 Parking Spots
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exc ...
From $282 per night (USD)
VRBO
From $1012 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $1012 per night (USD)
VRBO
From $1588 per night (USD)
VRBO
Private Pool Paradise Modest Socials Welcomed
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Beautiful property with spacious home and grounds perfect for a modest get together of friends and family. If you’re int ...
From $1588 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Walk to Waterfront from Eastport Gem w Fire Pit, Porch & Fenced-In Yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Experience the Difference: Professionally Managed by iTrip Annapolis Walk to waterfront restaurants, hop the water taxi ...
From $559 per night (USD)
Expedia
From $196 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 $196 per night (USD)
VRBO
From $456 per night (USD)
VRBO
★ Odenton Oasis ★ Patio - Central to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our beautifully furnished, colonial-style townhome just minutes from MARC station with great proximity to DC, ...
From $456 per night (USD)
VRBO
From $568 per night (USD)
VRBO
BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
The house is in a quiet residential neighborhood. It has easy access to all major routes: I-97, I-695, I-95, I-295, rout ...
From $568 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Very cozy bedrooms with two incredible family rooms to enjoy internet tv, game room, built in bar, beautiful screened in ...
From $585 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Downtown Gem! Historic Carriage House Steps to Main St, City Dock & USNA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the Difference: Professionally Managed by iTrip Annapolis Originally built in 1857, this fully-restored home ...
From $587 per night (USD)
VRBO
From $675 per night (USD)
Expedia
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 $675 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Spacious Townhouse in the Heart of Washington D.C.
Bedrooms:
1
Bathrooms:
1
Sleeps:
7
Summary Enjoy a clean, quiet and spacious place to call your home. Best for visiting the landmarks of Washington DC. Loc ...
From $499 per night (USD)
VRBO
From $1352 per night (USD)
Expedia
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 $1352 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect Annapolis escape — a beautifully appointed, fully furnished cottage where every detail has been ...
From $395 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Chesapeake Bay Loft Retreat | Walk to Water | Sleeps 2 | 20 Min to Annapolis Your perfect summer escape starts here. W ...
From $329 per night (USD)
Expedia
From $800 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 $800 per night (USD)
VRBO
From $467 per night (USD)
VRBO
Charming Renovated Historic Home Downtown wParking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cute and comfortable home in the heart of the HISTORIC DISTRICT of DOWNTOWN Annapolis. Park the car (a spot is included) ...
From $467 per night (USD)
VRBO
From $506 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 $506 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Walk to the Chesapeake Bay! Herrington Harbour is a few blocks away.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Herrington Harbour South, Rose Haven's 2 acre waterfront park or the market, hair salon, bar and restaurant. Th ...
From $475 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Fleet St Retreat in Downtown - Great Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
We welcome you to our renovation on historic Fleet Street. Purchased in 2016 this house was taken down to the studs so e ...
From $304 per night (USD)
VRBO
From $428 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 $428 per night (USD)
VRBO
From $2908 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 $2908 per night (USD)
VRBO
From $678 per night (USD)
Expedia
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $678 per night (USD)
Expedia
From $1390 per night (USD)
VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. You feel li ...
From $1390 per night (USD)
VRBO
From $224 per night (USD)
VRBO
A Serene Tiny Home Experience
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnish ...
From $224 per night (USD)
VRBO
From $494 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 $494 per night (USD)
VRBO
From $291 per night (USD)
Expedia
New Downtown Annapolis Condo With Free Parking
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 $291 per night (USD)
Expedia
From $990 per night (USD)
VRBO
West Annapolis Cottage- 6BR Walk to Navy Stadium
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: Spacious 6BR/5BA Annapolis retreat, perfect for large groups & families! Recently renovated with a chef's kitc ...
From $990 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Waterfront Retreat in Riva· Pool, Pier & Kayaks · Sleeps 9 · 15 Min to Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
La Maison is a modern waterfront home set directly on the peaceful South River, offering sweeping water views from nearl ...
From $559 per night (USD)
Expedia

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