Anne Arundel Area Rentals
- From $716 per night (USD)
VRBO
New Waterfront Home on the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
New built waterfront home with sweeping views of the Chesapeake Bay located on a quiet, private road in the community of ...
From $716 per night (USD)VRBO
- From $177 per night (USD)
VRBO
Annapolis\/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $177 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Quality and Dependable!! 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You’ll find our guest rooms spacious, affordable and comfortable. Whether your tucking into our huge beds and soft beddi ...
From $119 per night (USD)VRBO
- From $500 per night (USD)
VRBO
All-stop. Rental Midships.
- Bedrooms:
- 3
- 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 $500 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Renovated Rowhome in the Heart of Downtown Annapolis Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR-145006 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $350 per night (USD)VRBO
- From $342 per night (USD)
VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $342 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Chesapeake Cottages- 2 Quaint Waterfront Retreats
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Our tastefully appointed cottages sit on almost an acre of waterfront land. Peaceful and tranquil, yet close to shops an ...
From $425 per night (USD)VRBO
- From $442 per night (USD)
VRBO
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $442 per night (USD)VRBO
- From $173 per night (USD)
VRBO
Free Breakfast Buffet! Pool | Staybridge Near BWI Airport
- 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 $173 per night (USD)VRBO
- From $176 per night (USD)
VRBO
Shared Pool. Near BWI Airport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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 $176 per night (USD)VRBO
- Click For Pricing
VRBO
WALK TO THE STADIUM! Gorgeous, newly built 5 bedroom home.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
USNA grad owned! Beautiful house (built in 2017) located less than two blocks from Navy-Marine Corps Memorial Stadium, w ...
Click For PricingVRBO
- From $425 per night (USD)
VRBO
The Liberty House- Pristine Renovation with parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $425 per night (USD)VRBO
- From $2172 per night (USD)
VRBO
Relax at our 4-acre South River Waterfront with a Saltwater Pool near Annapolis
- Bedrooms:
- 6
- Bathrooms:
- 10
- Sleeps:
- 24
Welcome to your serene retreat on the South River! Nestled on a 4-acre parcel, this enchanting property offers a perfect ...
From $2172 per night (USD)VRBO
- From $882 per night (USD)
VRBO
Riva Waterfront *The Luxe*
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to The Luxe! A newly renovated 5 bedroom 3.5 bath home on the South River, 15 minutes outside of downtown Annapo ...
From $882 per night (USD)VRBO
- Click For Pricing
VRBO
Free Parking and Hot Tub at Pet Friendly Annapolis-themed home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Annapolis-themed 3 Bedroom home now has a new hot tub! It has a twin sister next-door, The MidshipDen, and is a mir ...
Click For PricingVRBO
- From $262 per night (USD)
Expedia
Parking & Pet Friendly USNA-themed Annapolis home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Flexible Commissioning Week Cancellation Policy** This Naval Academy-themed 3 Bedroom home was just fully renovated a ...
From $262 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $450 per night (USD)VRBO
- From $393 per night (USD)
VRBO
Cozy Annapolis Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $393 per night (USD)VRBO
- From $516 per night (USD)
VRBO
★ Midcentury Modern Getaway ★ Prime Location ★
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $516 per night (USD)VRBO
- From $218 per night (USD)
Expedia
The Heron's Nest at Atlantic Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bay breezes and magnificent views make this quaint cottage the perfect getaway! Only steps away from the beach, this n ...
From $218 per night (USD)Expedia
- Click For Pricing
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
Click For PricingVRBO
- From $492 per night (USD)
VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $492 per night (USD)VRBO
- Click For Pricing
VRBO
River Cottage with Beach and Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Get away from the city to this charming cottage on the West River- a calm inlet right off the Chesapeake Bay. Crab or fi ...
Click For PricingVRBO
- From $875 per night (USD)
Expedia
La Maison - Stunning waterfront views with pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Light-filled, modernly furnished 4-bedroom, 2.5 bathroom waterfront house on the South River, with a private pool - minu ...
From $875 per night (USD)Expedia
- Click For Pricing
VRBO
Less than a block from Main Street - Heart Of Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Circa 1847 Townhouse - one of the "Rainbow Houses" that was historically part of the Mann's Tavern. Renovated inside and ...
Click For PricingVRBO
- From $326 per night (USD)
VRBO
Walk to Naval Academy + City Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to The Constellation House, located in the heart of Downtown Annapolis! Within walking distance to the U.S. Nava ...
From $326 per night (USD)VRBO
- From $151 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 $151 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $2500 per night (USD)
VRBO
Nantucket on the Chesapeake Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2500 per night (USD)VRBO
- From $109 per night (USD)
Expedia
Private detached 1bedroom guest house.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Just few miles away from Baltimore downtown, Ft Meade, NSA, Annapolis and Washington DC. Less than 5 miles away from BWI ...
From $109 per night (USD)Expedia
- Click For Pricing
VRBO
Quiet & Relaxing Waterfront Home Near Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Quiet and Relaxing Waterfront home 5 minutes from Downtown Annapolis. Ideal for Business stays, Relocation Home, Get Tog ...
Click For PricingVRBO
- From $400 per night (USD)
VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
- Bedrooms:
- 2
- 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 $400 per night (USD)VRBO
- From $298 per night (USD)
VRBO
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
We welcome you to our brand new listing on Fleet Street . Purchased in 2016 and taken down to the studs this property is ...
From $298 per night (USD)VRBO
- From $177 per night (USD)
VRBO
The Cool, Pool - BWI - Work Here - Fully Stocked - Fast Internet
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Entire apartment near the BWI airport and BWI business district. During this time, it is very important to provide a cl ...
From $177 per night (USD)VRBO
- From $204 per night (USD)
VRBO
The Artist, Fast Internet - Pool - BWI - Gym - New Listing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Entire apartment near the BWI airport and BWI business district. During this time, it is very important to provide a cl ...
From $204 per night (USD)VRBO
- From $192 per night (USD)
VRBO
The Golden City, Gym - Pool - Fast Internet - Fully Stocked - BWI - New Listing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Entire apartment near the BWI airport and BWI business district. During this time, it is very important to provide a cl ...
From $192 per night (USD)VRBO
- From $186 per night (USD)
VRBO
The Savvy Traveler, Pool - Gym - Fast Internet - BWI - New Listing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Entire apartment near the BWI airport and BWI business district. During this time, it is very important to provide a cl ...
From $186 per night (USD)VRBO
- From $233 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 $233 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Renovated Historic Home located downtown with parking - Walk everywhere !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
❤️❤️New kitchen , 2 system central AC and Heat , parking spot , Master bath and deck installed in 2021 New patio in Sp ...
From $295 per night (USD)VRBO
- From $349 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 $349 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Fall at the beach! Check our weekly discount! Near Herrington Harbour South.
- 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 $350 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
Beautiful 4BR Waterfront Home in Historic Downtown Annapolis - Close Proximity to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1100 per night (USD)Expedia
- From $107 per night (USD)
VRBO
West Annapolis Condo! Ideal location - Close to downtown Annapolis and commuter routes
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
STR-143827 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $107 per night (USD)VRBO
- From $1429 per night (USD)
Expedia
A huge deck and screen porch on this contemporary cape in Edgewater offers great views of Beard's Creek and out onto the South River.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
STR-395 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTE ...
From $1429 per night (USD)Expedia
- From $800 per night (USD)
VRBO
Delightful large Historic Downtown Annapolis Victorian 4BR home has been lovingly restored.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $800 per night (USD)VRBO
- From $142 per night (USD)
VRBO
Golfers? Kids? Pets? This elegant town home is beautifully furnished and is located in the Bay Hills golf course community.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $142 per night (USD)VRBO
- From $716 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 $716 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Downtown Historic District Annapolis Town Home (built in 2008) with Garage Parking!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
REN08-139834 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $183 per night (USD)Expedia
- Click For Pricing
VRBO
Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleeps 16!!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
STR266 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED ...
Click For PricingVRBO
- From $106 per night (USD)
VRBO
Charming \"doll house\" in a delightful Eastport neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $106 per night (USD)VRBO
- Click For Pricing
VRBO
Gorgeous renovation in HistoricDistrict -New listing !
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our newest listing in Downtown Annapolis. Brand new renovation with a nautical flair this is the perfect spot ...
Click For PricingVRBO
- From $900 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 $900 per night (USD)Expedia
- Click For Pricing
VRBO
Lovely contemporary in water-privileged community
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
Click For PricingVRBO
- From $650 per night (USD)
VRBO
Perfect weekend getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town ce ...
From $650 per night (USD)VRBO
- From $643 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 $643 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Charming cottage - easy walk to downtown with parking
- 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 $275 per night (USD)VRBO
- From $370 per night (USD)
VRBO
2 BR home in historic Downtown Annapolis. Walk to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $370 per night (USD)VRBO
- From $1125 per night (USD)
Expedia
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1125 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Annapolis Historic District row home with 1 small off street parking space and a small rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR-143392 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $416 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Charming 3 BR\/2BA home at Arundel on the Bay features a community beach, boat slips, playground.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR-000324 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $475 per night (USD)Expedia
- From $754 per night (USD)
VRBO
Elegant yet modern historic home in the heart of downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $754 per night (USD)VRBO
- From $565 per night (USD)
Expedia
Charming 3BR house in the Heart of the Annapolis Historical District - 3rd fl. private suite
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR-143804 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $565 per night (USD)Expedia
- From $457 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 $457 per night (USD)VRBO
- From $1071 per night (USD)
Expedia
4 BR Colonial home just outside of Annapolis - Beautiful 4 Seasons room overlooking fenced backyard with beautiful pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1071 per night (USD)Expedia
- From $1000 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 $1000 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all. 3 sides of direct bay waterfront.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
STR-250 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1100 per night (USD)Expedia
- From $1519 per night (USD)
VRBO
Behold your perfect Annapolis getaway home! Gorgeous 4 bdrm, 2.5 bath with breathtaking views of the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR129 Please note: If you request to book this property, your reservation is not confirmed until you are contacted by ...
From $1519 per night (USD)VRBO
- From $550 per night (USD)
Expedia
3BR Rowhome in Historic District - with Garage Parking for 1 - Location=AMAZING!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 - Please note: THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YO ...
From $550 per night (USD)Expedia
- From $1177 per night (USD)
VRBO
Murray Hill Gem! Enjoy your Annapolis stay in the beautiful 4 BR\/3 BA historic home.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145062 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $1177 per night (USD)VRBO
- Click For Pricing
VRBO
Large secluded\/wooded 4 bedroom home with waterview!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This unique contemporary waterfront home features gorgeous views of Maccubin's Cove! Set up your home office in the bonu ...
Click For PricingVRBO
- From $683 per night (USD)
VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
STR-143320 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $683 per night (USD)VRBO
- From $160 per night (USD)
Expedia
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 $160 per night (USD)Expedia
- From $83 per night (USD)
VRBO
Gorgeous Edgewater home with in-law apartment has beautiful wood floors, high ceilings and crown molding throughout.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $83 per night (USD)VRBO
- From $439 per night (USD)
Expedia
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 $439 per night (USD)Expedia
- From $1175 per night (USD)
VRBO
Spacious 4 BR with first FL. BR in Eastport is close to everything! AND PARKING!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
REN-00085 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1175 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
Beautiful home w\/elevator going to every floor. This house is accessible to all.
- Bedrooms:
- 4
- 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 $1100 per night (USD)Expedia
- From $382 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 $382 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Spacious 4 BR with first FL. BR in Eastport is close to everything! AND PARKING!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
REN - 00086 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $200 per night (USD)Expedia
- From $595 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 $595 per night (USD)VRBO
- Click For Pricing
VRBO
Annapolis Family Vacation Rental: Close to downtown and the Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located: 4.1mi (10 min) from Naval Academy: Annapolis Cove Neighborhood Open floor plan: Kitchen open to living room/sc ...
Click For PricingVRBO
- From $330 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 $330 per night (USD)VRBO
- From $375 per night (USD)
VRBO
★ Odenton Oasis ★ Patio - Central to Everything
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our beautifully furnished, colonial-style townhome just minutes from MARC station with great proximity to DC, ...
From $375 per night (USD)VRBO
- From $70 per night (USD)
VRBO
Charming 1 BDApt - 6 Minutes from BWI Airport, close to Ft. Meade and Baltimore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Less than 5 minutes from BWI Airport, near Fort Meade and 10 minutes to charming Baltimore City by car or Uber. This coz ...
From $70 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Charming Annapolis Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $237 per night (USD)VRBO
- From $890 per night (USD)
VRBO
Private Waterview Estate with 4 bedroom Suites & Hot Tub
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Sanare Estates! The ultra-private waterfront estate is like your own luxury resort, located on 20+ Acres with ...
From $890 per night (USD)VRBO
- From $620 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $620 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Covid 19 updates. In addition to blocking time between guests per CDC guidelines our professional cleaning staff is p ...
From $140 per night (USD)VRBO
- From $387 per night (USD)
Expedia
NEW 4 Bedroom Home with Pier by Water
- Bedrooms:
- 3
- 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 $387 per night (USD)Expedia
- From $185 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment Two A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The place to be for all USNA activities. Annapolis is a city abundant with history and culture. This former capital of t ...
From $185 per night (USD)VRBO
- From $2200 per night (USD)
VRBO
Cool 1870's Historic District Home with modern amenities.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
150 year old, five bed and three bath home with 3,000 square feet is centrally situated in the heart of the Historic Di ...
From $2200 per night (USD)VRBO
- From $163 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment Two B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $163 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely renovated street level 1 bedroom apartment with all the amenities of home. Perfect for a single traveler or ...
From $200 per night (USD)VRBO
- Click For Pricing
VRBO
The Cozy Suite .....
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Cozy Suite is a delightful cozy space for rest and relaxation. The Cozy Suite is partially above grade and the entra ...
Click For PricingVRBO
- From $90 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 $90 per night (USD)VRBO
- From $525 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 $525 per night (USD)VRBO
- From $225 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 $225 per night (USD)VRBO
- From $431 per night (USD)
VRBO
Beautiful Historic Home With Great Location!
- Bedrooms:
- 3
- 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 $431 per night (USD)VRBO
- From $376 per night (USD)
Expedia
Million Dollar View of the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
'Fredelig sted'(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine a ...
From $376 per night (USD)Expedia
- From $1040 per night (USD)
VRBO
Stunning colonial p on a private 1.6 acre lot situated on Broadneck Peninsula.
- 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 $1040 per night (USD)VRBO
- From $1035 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 $1035 per night (USD)VRBO