Anne Arundel Area Rentals
- From $295 per night (USD)
VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $295 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis \/USNA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from ...
From $425 per night (USD)Expedia
- From $546 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $546 per night (USD)VRBO
- From $550 per night (USD)
Expedia
1 Block to USNA with Chapel Views big back patio and off-site parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $550 per night (USD)Expedia
- From $505 per night (USD)
VRBO
Hanover House across from USNA Gate 3 with private back patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $505 per night (USD)VRBO
- From $173 per night (USD)
Expedia
Tranquility Awaits
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and single. Full kitchen, laundry, de ...
From $173 per night (USD)Expedia
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VRBO
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
Click For PricingVRBO
- From $500 per night (USD)
Expedia
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 $500 per night (USD)Expedia
- From $661 per night (USD)
VRBO
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 $661 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $802 per night (USD)
Expedia
Steps to Gate 1 and Free Parking at Naval-Academy Themed Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking ...
From $802 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $555 per night (USD)
Expedia
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Please note 2026 and beyond commissioning week will need to be confirm ...
From $555 per night (USD)Expedia
- From $172 per night (USD)
VRBO
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 ...
From $172 per night (USD)VRBO
- From $232 per night (USD)
Expedia
Serenity Place in Annapolis- EV Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Serenity Place, your serene and clean vacation home with comfortable sleeping arrangements and strong wifi! ...
From $232 per night (USD)Expedia
- From $695 per night (USD)
VRBO
Heart of Downtown, superior location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Steps from the Annapolis City Dock and U.S. Naval Academy- Walk to all Shops, Restaurants, and Downtown Events. This pr ...
From $695 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Newport Condominium has a beautiful water view of Spa Creek in Eastport. This condo is newly decorated with new ca ...
From $189 per night (USD)Expedia
- From $556 per night (USD)
VRBO
Pristine Waterfront Home with Expansive Views.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
**Monthly discounts only apply for Off-Season rentals (October-April) If relaxing in luxury on the water is what you a ...
From $556 per night (USD)VRBO
- From $423 per night (USD)
VRBO
Waterfront Yacht Life!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Don't miss this rare opportunity to vacation aboard Sojourn, a beautiful, comfortable 2022 46+ ft. sailboat with stunnin ...
From $423 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Charming Charles Retreat- The perfect space for fun and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
From $228 per night (USD)VRBO
- From $498 per night (USD)
VRBO
Suite Retreat Luxurious 3 BR, 3 BathRoom Rancher has game room and house keeper.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Looking for a luxurious short term rental that will take your breath away, look no further than our stunning Suite Retre ...
From $498 per night (USD)VRBO
- From $203 per night (USD)
VRBO
Pasadena Hideaway w\/ Game Room & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
From hosting afternoon picnics to making memories in the game room, this Pasadena vacation rental has everything you nee ...
From $203 per night (USD)VRBO
- From $378 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $378 per night (USD)VRBO
- From $268 per night (USD)
VRBO
Glen Burnie Vacation Rental w\/ Private Deck!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the best of the East Coast from this spacious 3-bed, 5-bath vacation rental in Glen Burnie. Located just a shor ...
From $268 per night (USD)VRBO
- From $634 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $634 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Cozy Zen House
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 9
This clean cozy home is decorated with earth tones for a more relaxed and chill good-vibes-only experience. Clean comfor ...
From $150 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Six bedroom 2020 Fountaine Pajot catamaran
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Beautiful 6 bedroom 6 bathroom catamaran just miles from downtown Annapolis on the South River from June to November. Sa ...
From $1000 per night (USD)Expedia
- From $2400 per night (USD)
VRBO
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Why rent a hotel when you can be in a Floatel on a Fountaine Pajot Saba luxurious 50 foot catamaran six Cabin six head l ...
From $2400 per night (USD)VRBO
- From $733 per night (USD)
Expedia
Waterfront 5 Bedroom Near BWI\/Annapolis\/Baltimore
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Escape to paradise in this stunning 5-bedroom private waterfront oasis, only 20 minutes from BWI airport, US Na ...
From $733 per night (USD)Expedia
- From $210 per night (USD)
VRBO
Bung-a-flo Tiny Bohemian Designed Floating Home w\/ 360 Waterfront Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
| OVERVIEW | Welcome aboard FLOHOM 3 | Bung-a-flo, a Bohemian-inspired floating tiny home docked at the scenic Ferry P ...
From $210 per night (USD)VRBO
- Click For Pricing
Expedia
1 bedroom 1 bath 10-15 minutes to Maryland live Casino . KITCHEN.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
15 minutes Maryland live Casino and BWI airport and 15-20 minutes to Baltimore . 20-25 min Annapolis , Walmart , Planet ...
Click For PricingExpedia
- From $527 per night (USD)
VRBO
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
From $527 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Dog-Friendly Crofton Home: 13 Mi to Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Guarantee your next getaway is spent staying in style when you book this Crofton home-away-from-home! With a vibrant int ...
From $295 per night (USD)Expedia
- From $235 per night (USD)
VRBO
SYR Properties
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space We aim to provide guests with a clean, comfortable, and safe "home away from home." Our location is con ...
From $235 per night (USD)VRBO
- From $78 per night (USD)
Expedia
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Blackout curtains are just perfect for a good night’s sleep, a restaurant district, and a night sky perfect for stargazi ...
From $78 per night (USD)Expedia
- Click For Pricing
Expedia
~Home Away From Home~ (2) Lower Level Rooms! (ALL TO YOURSELF, NOT SHARED)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
You'll stay in (2) lower level bedrooms with bunkbed and double bed and will have access to kitchen, living room, and 1. ...
Click For PricingExpedia
- Click For Pricing
Expedia
Deluxe King Suite
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy easy access to everything from this centrally located place. Located minutes from BWI airport, and within ...
Click For PricingExpedia
- From $60 per night (USD)
VRBO
Executive King Suite\/ Entire House
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
You will enjoy easy access to everything from this centrally located place. Located minutes from BWI airport, and within ...
From $60 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $320 per night (USD)Expedia
- From $2300 per night (USD)
VRBO
Premium Home in West Annapolis: Perfect for Navy Events, Boat Shows, Walkable!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
You will be close to everything when you stay at this well appointed, centrally-located home. This elegant, stylish, a ...
From $2300 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Cute bungalow blocks to Stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $138 per night (USD)Expedia
- From $48 per night (USD)
VRBO
~ Entire Guest House ~
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Hi. This property is pretty spacious and always undergoing upgrades to improve. There is a larger than standard size ref ...
From $48 per night (USD)VRBO
- From $1643 per night (USD)
VRBO
Elegant Eastport Entertaining Dream House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NBS23-145363 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1643 per night (USD)VRBO
- Click For Pricing
VRBO
Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR00803 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
Click For PricingVRBO
- Click For Pricing
Expedia
Marvelous Home with Backyard Living Room in Murray Hill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
Click For PricingExpedia
- Click For Pricing
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
Click For PricingVRBO
- From $733 per night (USD)
Expedia
5 Min to Downtown Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This brand-new build Eastport luxury home has everything you and your guests need for an upgraded stay in Annapolis. Eac ...
From $733 per night (USD)Expedia
- From $152 per night (USD)
VRBO
Minutes from History: Room w\/ Free Breakfast Near Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $152 per night (USD)VRBO
- From $181 per night (USD)
VRBO
Enjoy Complimentary Breakfast at Our Welcoming Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $181 per night (USD)VRBO
- From $155 per night (USD)
VRBO
Annapolis Adventure: Room w\/ Outdoor Pool + Easy Access to Historic Sites
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $155 per night (USD)VRBO
- From $100 per night (USD)
Expedia
Luxury entire place BWI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Quiet place close to the BWI airport and a lot of beautiful attractions, 40 mins away from Washington DC, we going to do ...
From $100 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Annapolis Home on Black Walnut Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Single Family home on Black Walnut Creek located in the Bay Highlands community, Annapolis, MD https://www.bayhighlands. ...
From $375 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $254 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 $254 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Cozy One Bedroom Basement Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to our fully furnished basement apartment, a cozy and convenient retreat located in a peaceful neighborhood clos ...
From $125 per night (USD)Expedia
- From $242 per night (USD)
VRBO
The Annapolis Pinkney House- complete with parking!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to the Naval ...
From $242 per night (USD)VRBO
- From $249 per night (USD)
VRBO
Spacious basement apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Plenty of room in this 2000+ sq ft spacious basement apartment with queen size bed, lots of couches, full bath and dry b ...
From $249 per night (USD)VRBO
- From $785 per night (USD)
VRBO
315) Waterfront with Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Escape to paradise in this stunning 5-bedroom private waterfront oasis, only 20 minutes from BWI airport, US Naval Acade ...
From $785 per night (USD)VRBO
- From $633 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 3
- 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 $633 per night (USD)VRBO
- From $555 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 $555 per night (USD)VRBO
- From $682 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 19
Welcome to The Compass Rose, a serene haven with backyard shoreline surrounded by 4+ acres of pristine woods. Enjoy excl ...
From $682 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
Click For PricingVRBO
- From $585 per night (USD)
VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $585 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a beautiful spacious 5 bedroom 3.5 bath home in a quiet wooded setting overlooking the Magothy River. The home inc ...
Click For PricingVRBO
- From $450 per night (USD)
VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $450 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The charming home is a 3 bedroom 2 full bath that's been professionally decorated and has exotic tiger hardwood flooring ...
From $463 per night (USD)VRBO
- Click For Pricing
Expedia
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Beautiful waterfront property with a private beach and dock thirty minutes from Annapolis. Perfect for family reunions o ...
Click For PricingExpedia
- Click For Pricing
VRBO
Annapolis Entertainment Complex
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous four bedroom four bathroom home in Arnold that sleeps 10 is perfect for entertaining while you’re in Annap ...
Click For PricingVRBO
- From $499 per night (USD)
VRBO
5-years young STUNNING home with water view!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
5-years-young STUNNING home with OPEN concept, soaring ceilings, hardwoods, gas fireplace, separate laundry room, backya ...
From $499 per night (USD)VRBO
- Click For Pricing
VRBO
Luxury Catamaran Liveaboard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Live Wide" is a unique luxury 44 ft Antares Catamaran Yacht creating a memorable experience for a overnight, weekend or ...
Click For PricingVRBO
- From $339 per night (USD)
VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $339 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $400 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Historic Annapolis Home And Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This delightful two bedroom, two full bath duplex occupies the second and third floors of a lovely home built in 1900, u ...
From $350 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs ...
From $383 per night (USD)VRBO
- From $1610 per night (USD)
Expedia
New Waterfront Home near Annapolis, MD
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful waterfront home built in 2013 located on 75 acres of picturesque farmland. Exceptional, award-winning architec ...
From $1610 per night (USD)Expedia
- From $745 per night (USD)
VRBO
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Conveniently located just 4.5 miles from historic Annapolis the Coastie Cottage is the perfect homebase for your next vi ...
From $745 per night (USD)VRBO
- From $272 per night (USD)
VRBO
Wonder Cottage@Chesapeake Paradise Kayaks\/Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Listing Description: Escape the city hustle to relax on the Chesapeake! Savor our three-bedroom Cottage in this peaceful ...
From $272 per night (USD)VRBO
- From $645 per night (USD)
VRBO
Waterfront Oasis in Eastport - Walk to Downtown and USNA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our newest listing in listing in the Maritime section of Annapolis . This upscale , fully renovated waterfron ...
From $645 per night (USD)VRBO
- From $375 per night (USD)
VRBO
PERFECT LOCATION in the heart of history
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $375 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $300 per night (USD)VRBO
- From $480 per night (USD)
VRBO
Large Contemporary in Wooded Privacy
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Lovely, contemporary sitting on three and-a-half acres of wooded beauty. Lots of glass and cedar. Open and airy floor pl ...
From $480 per night (USD)VRBO
- From $791 per night (USD)
VRBO
Riva Waterfront *The Cottage*
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This home is located in Riva Maryland, adjacent to Annapolis Maryland. #GoNavy ! This hidden gem sits on 4 acres of la ...
From $791 per night (USD)VRBO
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VRBO
Craftsman Home in Annapolis Waterfront Suburb
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful, family-friendly home in St. Margaret's area of Annapolis. Only a few miles from downtown, the stadium and all ...
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- From $780 per night (USD)
VRBO
Excellent Location, Super Clean, Super Spacious \/ Near Bay & Downtown Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
Located in safe residential neighborhood. Backyard is a private wooded Oasis! Close to shopping, restaurants and the Che ...
From $780 per night (USD)VRBO
- From $910 per night (USD)
VRBO
USNA Stay w\/ Private Pool, Indoor Soft Hot Tub, King Beds, & CHILD FRIENDLY GEAR
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $910 per night (USD)VRBO
- From $169 per night (USD)
VRBO
Free Breakfast. Outdoor Pool. Near BWI Airport. | Staybridge King Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $169 per night (USD)VRBO
- From $193 per night (USD)
VRBO
Ideal Eastport\/ Annapolis Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious, fully furnished one bedroom1st floor apartment is perfectly located and has everything you need for your ...
From $193 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This fully renovated three bedroom home sleeps 8. A touch of Key West comes to Eastport in this beautiful cottage style ...
From $444 per night (USD)VRBO
- From $230 per night (USD)
VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis \/ Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $230 per night (USD)VRBO
- From $703 per night (USD)
VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
BOOK YOUR ANNAPOLIS VACATION AT BURLEY CREEK HIDEAWAY! Charming home owned by USNA grads. Lovely waterfront two-level ...
From $703 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Charming English Cottage in the heart of Eastport - park the car and walk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Restored and charming 2 bedroom 1.5 bath historic (circa 1921) cottage located in the heart of the popular Eastport and ...
From $239 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Chesapeake Bay Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In less than an hour from the D.C. Metro area you're transported to your own private shore on the Chesapeake Bay. This ...
From $299 per night (USD)VRBO
- From $170 per night (USD)
VRBO
King Suite Near BWI Airport. Free Breakfast Buffet, Pool Access | Staybridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $170 per night (USD)VRBO
- From $153 per night (USD)
VRBO
House of Cardz- comforts of home by LLOYD SUITES
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
SUMMARY We are pleased to bring you the "House of Cardz". This is our newest listing since launching the popular "Whiske ...
From $153 per night (USD)VRBO
- From $211 per night (USD)
VRBO
Truly Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cute cottage tucked away amongst the trees on Stoney Creek in Pasadena Md. Enjoy bird watching from the upper deck just ...
From $211 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Charming Annapolis WaterVIEW Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters o ...
From $299 per night (USD)VRBO
- From $290 per night (USD)
VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $290 per night (USD)VRBO
- From $98 per night (USD)
VRBO
Hanover!!! Full blast of Fun! Relax and Enjoy!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The property features coffee/tea in a common area, a seasonal outdoor pool, and a business center. Free WiFi in public a ...
From $98 per night (USD)VRBO
- Click For Pricing
VRBO
Brick Georgian w\/pool, 1-2 miles to all! Pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Lovely brick Georgian built in the 1920s with secluded heated inground pool, located in a quiet, beautiful waterfront ne ...
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