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From $519 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 $519 per night (USD)
VRBO
From $239 per night (USD)
VRBO
New Bungalow with view of South River!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern bungalow that ha ...
From $239 per night (USD)
VRBO
From $920 per night (USD)
VRBO
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views, and private salt-water pool, perfect for tha ...
From $920 per night (USD)
VRBO
From $485 per night (USD)
VRBO
Tastefully decorated fully-equipped Eastport Annapolis house with water views
Bedrooms:
3
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 $485 per night (USD)
VRBO
$Private Waterfront Home w\/ Pier and 2+ Acres!$
From $521 per night (USD)
VRBO
Private Waterfront Home w\/ Pier and 2+ Acres!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
For endless water views and enviable privacy - look no further! Situated on two acres of lush green grass, this true pen ...
From $521 per night (USD)
VRBO
$Cozy 2br home w\/ parking in downtown Annapolis$
From $324 per night (USD)
Expedia
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 $324 per night (USD)
Expedia
$Nice retreat apartment\/private patio, min. away from USNA & Downtown Annapolis$
Click For Pricing
VRBO
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
VRBO
$Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break\n$
From $310 per night (USD)
Expedia
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Welcome to Firefly Cottage in beautiful Cape St. Claire! Our cozy cottage sits on a ¼ acre of land for your exclusive u ...
From $310 per night (USD)
Expedia
From $369 per night (USD)
VRBO
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 $369 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Sweet Bamboo Beach Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
If you are looking for a sweet, comfortable and clean home for your stay while visiting our beaches or other Calvert Cou ...
From $200 per night (USD)
VRBO
From $1100 per night (USD)
VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
Bedrooms:
4
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 $1100 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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 $291 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Beautifully Renovated Historic District Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $573 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Charming Historic Annapolis Home With Two Off-street Parking Places!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $759 per night (USD)
Expedia
From $1077 per night (USD)
VRBO
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lovely 3 bedroom house, beautifully furnished, 2 gourmet kitchens, outdoor oasis with pool, jacuzzi, sauna, steam room ...
From $1077 per night (USD)
VRBO
$Huge Beach Bungalow w\/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants$
From $513 per night (USD)
Expedia
Huge Beach Bungalow w\/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This huge, newly designed home has 4 bedrooms (2 king beds + 2 queen beds). It is a few minutes to the beach, restaurant ...
From $513 per night (USD)
Expedia
From $647 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 $647 per night (USD)
VRBO
From $533 per night (USD)
VRBO
Our Home on the Cove: waterfront, peaceful, wooded, comfy, family friendly
Bedrooms:
2
Bathrooms:
7
Sleeps:
15
Sitting on 8 acres of water front property, Our Home on the Cove is a cottage with 5 bedrooms and room for a family of 4 ...
From $533 per night (USD)
VRBO
$A WATERFRONT ESTATE ON THE CHESAPEAKE BAY, \THE DRIFTWOOD LODGE\.$
From $1312 per night (USD)
VRBO
A WATERFRONT ESTATE ON THE CHESAPEAKE BAY, \"THE DRIFTWOOD LODGE\".
Bedrooms:
5
Bathrooms:
7
Sleeps:
20
Enjoy panoramic waterfront views of the Chesapeake Bay, in this awe inspiring moment surrounded by nature. The home is s ...
From $1312 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy 1-bed with pool access, just steps from mall.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Studio basement apartment just steps from Waugh Chapel Outdoor Mall & IMAX Theater, Gambrills. Hot Plate/Air Fryer/Micro ...
Click For Pricing
Expedia
From $469 per night (USD)
VRBO
Waterfront, Private Beach, Peaceful Family Getaway
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience the Chesapeake from your very own front row seat at Murphy Point on the Chesapeake! Watch dolphins, turtles, ...
From $469 per night (USD)
VRBO
Click For Pricing
Expedia
Downtown Annapolis Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
Click For Pricing
Expedia
From $357 per night (USD)
VRBO
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 $357 per night (USD)
VRBO
From $193 per night (USD)
Expedia
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 $193 per night (USD)
Expedia
From $451 per night (USD)
VRBO
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 $451 per night (USD)
VRBO
$Jode's Retreat \Your home away from home$
From $231 per night (USD)
Expedia
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)
Expedia
From $584 per night (USD)
VRBO
Nautical Feel to This Beautiful Eastport Home
Bedrooms:
3
Bathrooms:
3
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 $584 per night (USD)
VRBO
From $471 per night (USD)
Expedia
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 $471 per night (USD)
Expedia
From $245 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 $245 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $1014 per night (USD)
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 ...
From $1014 per night (USD)
VRBO
From $774 per night (USD)
VRBO
80 Five Star Reviews & located in a quiet neighborhood in the City of Annapolis!
Bedrooms:
4
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 $774 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Waterfront Apartment with Fantastic Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
We call this recently renovated luxury apartment Hale Kai, which is Hawaiian for 'Sea House.' It is fully furnished and ...
From $182 per night (USD)
VRBO
From $1166 per night (USD)
VRBO
Relaxing Bay Ridge Lagoon
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Brand new to VRBO! We have been renting out for the Naval Academy Commissioning (Graduation) Week and now the house will ...
From $1166 per night (USD)
VRBO
From $641 per night (USD)
VRBO
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
Bedrooms:
3
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 $641 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Entire House Near BWI Airport Glen Burnie MD
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This is a brand-new house and is fresh and crisp. This house is located in the Ferndale area of Glen Burnie MD. The Fern ...
From $302 per night (USD)
VRBO
From $644 per night (USD)
VRBO
Ultraclean Family Waterfront Home Annapolis Area - 193+ 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 $644 per night (USD)
VRBO
From $353 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 $353 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Beautiful Waterfront Townhome In Historic Annapolis
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $690 per night (USD)
VRBO
From $195 per night (USD)
VRBO
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still only a 30 minute drive to Annap ...
From $195 per night (USD)
VRBO
From $1083 per night (USD)
Expedia
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Spacious 5-bedroom (4 full- and 2 half-baths) waterfront getaway built along the natural topography of Fairhaven Cliffs. ...
From $1083 per night (USD)
Expedia
From $806 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 $806 per night (USD)
VRBO
$Historic District\Crab Cakes and Football\$
From $479 per night (USD)
VRBO
Historic District\"Crab Cakes and Football\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $479 per night (USD)
VRBO
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 $1978 per night (USD)
VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Bedrooms:
4
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 $1978 per night (USD)
VRBO
$Pasadena, MD close to Annapolis\/WDC\/Baltimore$
From $328 per night (USD)
VRBO
Pasadena, MD close to Annapolis\/WDC\/Baltimore
Bedrooms:
3
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 $328 per night (USD)
VRBO
$Perfect family\/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb$
From $444 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 $444 per night (USD)
Expedia
From $750 per night (USD)
VRBO
34 Miles to DC Inauguration on the tranquil waters of Annapolis! 24 mi to Metro
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Attending Presidential inauguration festivities? Escape the crowds to the tranquility of Annapolis, MD; only 34 miles to ...
From $750 per night (USD)
VRBO
From $1553 per night (USD)
Expedia
Murray Hill Gem - Your Commissioning Week Home Away from Home
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
NBS22-145072 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $1553 per night (USD)
Expedia
From $242 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 $242 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. They will be given on request. Rates a ...
From $570 per night (USD)
VRBO
From $151 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 $151 per night (USD)
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 $392 per night (USD)
VRBO
Amazing views, short walks to great dining!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Valentine's Day weekend in Annapolis? "The view is better for two"! Annapolis Restaurant Week - February 22 to March ...
From $392 per night (USD)
VRBO
$Annapolis waterfront \tiny house\ in garden setting$
From $154 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 $154 per night (USD)
VRBO
From $684 per night (USD)
VRBO
Waterfront home on the Magothy River. Perfect for family vacation.
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Waterfront home in Severna Park on the Magothy River. Twenty minutes to the Chesapeake Bay by boat. Three bedrooms and f ...
From $684 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $215 per night (USD)
VRBO
From $218 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 $218 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Welcome to our newest property in The Exclusive Maritime Eastport section of Annapolis . Just a short stroll ( half mile ...
From $521 per night (USD)
VRBO
From $577 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 $577 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Charming Annapolis Victorian
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $852 per night (USD)
Expedia
From $2047 per night (USD)
VRBO
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
This home has everything for enjoying waterfront and poolside living, while also being very convenient to major tourist ...
From $2047 per night (USD)
VRBO
From $274 per night (USD)
Expedia
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
It was “MAGIC” when I discovered this town years ago. Beautiful sunrises right here on the Chesapeake Bay & glorious “mo ...
From $274 per night (USD)
Expedia
$Cute Bay Home\/Fantastic View and Sandy Beach$
From $351 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 $351 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Bell Estates-Brand New Bay View, Beautiful Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bell Estates is a newly built corner lot across the street from the bay with stunning views of the water from the Master ...
From $325 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Bedrooms:
2
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 $352 per night (USD)
VRBO
$National Historic home w\/ Serene & Quiet Setting$
From $231 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 $231 per night (USD)
VRBO
From $648 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 $648 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Annapolis Bay House BOAT SHOW & USNA Families 2 Bedroom with Den sleeps 5
Bedrooms:
3
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 $343 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront River Breezes with private pier, parking and billiards room
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
*Ask us about renting the 1Bedroom/1Bath River Cottage on the same property. This stunning historic home, located on 3 ...
Click For Pricing
VRBO
From $373 per night (USD)
VRBO
Historic Downtown Charmer, Water Views and Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $373 per night (USD)
VRBO
From $1202 per night (USD)
VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-r ...
From $1202 per night (USD)
VRBO
From $772 per night (USD)
Expedia
Historic home steps to Main St w Capital views, free off-site parking, patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Still available for Commissioning Week 2025! Experience Historic Annapolis in Comfort and Style This charming 4-bedroom ...
From $772 per night (USD)
Expedia
From $938 per night (USD)
VRBO
Annapolis -Eastport - -3 Bedroom- 3 bath with parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of nat ...
From $938 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Cozy 2 BR home with parking and views of the Annapolis Harbor - Walk to everything!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
STR23-145349 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $573 per night (USD)
Expedia
From $312 per night (USD)
VRBO
338 judysplaces in Lansdowne, 6BR, 2 BA, renovated SFH
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Welcome to a beautiful, totally renovated single family home in a quiet private neighborhood. Close to everything, about ...
From $312 per night (USD)
VRBO
From $1487 per night (USD)
VRBO
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)
VRBO
$Retreat on Sage Brush Court (Basement Suite w\/private entrance)$
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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 ...
Click For Pricing
VRBO
From $112 per night (USD)
VRBO
Whiskey Bottom Saloon by LLOYD SUITES
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SPACE You will have our entire Saloon for your enjoyment during your stay. The Saloon is located on the first level of t ...
From $112 per night (USD)
VRBO
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
$Waterfront Annapolis w\/swimming pool & pier -3 night stay CW 2025 available$
From $677 per night (USD)
VRBO
Waterfront Annapolis w\/swimming pool & pier -3 night stay CW 2025 available
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
In this lovely house in a quiet neighborhood in Annapolis, MD, you will find yourself just a short 12-minute car ride a ...
From $677 per night (USD)
VRBO
From $808 per night (USD)
VRBO
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
Bedrooms:
3
Bathrooms:
5
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 $571 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
3
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 $571 per night (USD)
Expedia
$Beautifully updated Annapolis Historic District rowhome w\/ parking and rooftop deck$
From $696 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 $696 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Chesapeake Bay single family home
Bedrooms:
4
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 $597 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Nora's Guest House- fine living by LLOYD SUITES
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary Nora's Guest House offers its guests a complete luxury home. We're 25 mins from DC, 20 mins from Baltimore, a fe ...
From $319 per night (USD)
VRBO
From $342 per night (USD)
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 ...
From $342 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Waterfront living 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 $396 per night (USD)
VRBO
From $215 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment One B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $215 per night (USD)
VRBO
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 $245 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 $245 per night (USD)
Expedia
From $270 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 $270 per night (USD)
VRBO
From $1284 per night (USD)
Expedia
RARELY AVAILABLE FOR COMMISSIONING WEEK! Stunning colonial on a private 1.6 acre lot!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
STR00844 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1284 per night (USD)
Expedia
From $1391 per night (USD)
VRBO
A most envious location! Home includes a beautiful gourmet kitchen with a dining area and a Guest House with Bedroom and Full Bath!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
STR 264 - PLEASE NOTE: THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HA ...
From $1391 per night (USD)
VRBO
From $1191 per night (USD)
VRBO
Luxurious home with parking in historic downtown Annapolis!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
NBS22-145083 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $1191 per night (USD)
VRBO
From $252 per night (USD)
VRBO
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 $252 per night (USD)
VRBO
From $308 per night (USD)
Expedia
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 $308 per night (USD)
Expedia
From $280 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 $280 per night (USD)
VRBO
$Indoor\/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!$
From $1688 per night (USD)
Expedia
Indoor\/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
STR21-144966 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1688 per night (USD)
Expedia

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