Anne Arundel Area Rentals
- From $1100 per night (USD)
VRBO
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)VRBO
- Click For Pricing
VRBO
Waterfront home in Eastport with Water taxi service available from property.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
Click For PricingVRBO
- 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)
Expedia
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)Expedia
- From $183 per night (USD)
VRBO
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)VRBO
- 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
Quaint Cottage is the perfect getaway retreat in Eastport.
- 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 ...
Click For PricingVRBO
- From $1566 per night (USD)
Expedia
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 $1566 per night (USD)Expedia
- From $629 per night (USD)
VRBO
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 $629 per night (USD)VRBO
- From $1177 per night (USD)
Expedia
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)Expedia
- 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 $743 per night (USD)
Expedia
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 $743 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $160 per night (USD)VRBO
- 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 $350 per night (USD)
VRBO
Fully Furnished 4 Bedroom\/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $350 per night (USD)VRBO
- From $99 per night (USD)
VRBO
Bright and cheery home. Just a short 2 blocks from the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
REN - 143722 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $99 per night (USD)VRBO
- From $1100 per night (USD)
VRBO
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)VRBO
- 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)
VRBO
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)VRBO
- From $800 per night (USD)
Expedia
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)Expedia
- From $264 per night (USD)
VRBO
Guest quarters at the inn - 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the -Bay in the historic and charming to ...
From $264 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful, clean and Peaceful surrounded by parks
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
There is a room to rent in a three level floor beautiful townhome . The bedrooms are on the third floor with a full bat ...
Click For PricingExpedia
- 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 $263 per night (USD)
Expedia
Guest quarters at the inn - 204
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $263 per night (USD)Expedia
- 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
- From $450 per night (USD)
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 ...
From $450 per night (USD)VRBO
- 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 $280 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 $280 per night (USD)VRBO
- From $95 per night (USD)
VRBO
Chesapeake Bayside Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently updated 1 bedroom, 1 bathroom loft studio unit with fully equipped kitchen, Smart TV in bedroom and free high s ...
From $95 per night (USD)VRBO
- Click For Pricing
VRBO
Modern Loft in Scenic Setting - NEW LISTING FOR POWER SHOW!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our loft is a quiet, private retreat in Arnold, just 15 minutes from Annapolis. Located above the garage of our home, it ...
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 $736 per night (USD)
Expedia
Vacation house near Downtown Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
Enjoy a weekend away in a secluded house in a lovely neighborhood right outside Annapolis. Our house is set back from th ...
From $736 per night (USD)Expedia
- Click For Pricing
VRBO
Look How Close! Annapolis gem near City Dock, USNA, Walk to Main & Market!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
ABOUT THE LOCATION: Just 1/4 mile walk to: — top restaurants (incl. Main & Market, Jack’s Fortune, and Starbucks) — publ ...
Click For PricingVRBO
- 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
- Click For Pricing
VRBO
Quiet One Bedroom for the traveling worker
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This is a quiet house with everything included except a washer and dryer. We share the kitchen and the bathroom. The hou ...
Click For PricingVRBO
- From $193 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 $193 per night (USD)VRBO
- From $171 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 $171 per night (USD)VRBO
- From $181 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 $181 per night (USD)VRBO
- From $193 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 $193 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Stunning Furnished Modern Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If location, convenience and access to amenities are important to you, this beautiful house is certainly worth considera ...
From $180 per night (USD)Expedia
- 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
- Click For Pricing
Expedia
Cute, cozy rancher close to down town Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For PricingExpedia
- From $333 per night (USD)
VRBO
Free Parking with private fenced-in backyard with pool table at Weekender
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly-renovated duplex townhome in Annapolis is walkable to Eastport and just 1.5 miles to the Annapolis Waterfront ...
From $333 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Large Crabtown Colonial near water 4bd\/4br
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Crabtown Colonial located in Severna Park is only 7 miles from Annapolis. Washington, D.C. Is 29 miles and Baltimore is ...
From $500 per night (USD)Expedia
- From $275 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 $275 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)
VRBO
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)VRBO
- 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 $99 per night (USD)
VRBO
1 Bedroom Basement Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Beautiful one Bedroom Basement apartment located in the beautiful Seven Oaks Community, Odenton, Maryland. - Walking d ...
From $99 per night (USD)VRBO
- From $473 per night (USD)
Expedia
Historic & sunny home w\/ Fireplace steps from USNA & Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $473 per night (USD)Expedia
- From $276 per night (USD)
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 ...
From $276 per night (USD)VRBO
- From $341 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 $341 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
- Bedrooms:
- 5
- 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 $800 per night (USD)VRBO
- From $148 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 $148 per night (USD)VRBO
- From $376 per night (USD)
VRBO
Plant-Filled Oasis Near Beach Town with Passes & Tips
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to A Haven Away! Relax in a plant-filled oasis which offers the perfect setting to unplug, relax, and connect wi ...
From $376 per night (USD)VRBO
- From $157 per night (USD)
VRBO
Lovely 3 bedroom 2 bath cottage Sleeps 6 just a few blocks from the water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a clean neat quaint home to stay while visiting the North Beach, Chesapeake Beach area? Well honey you have ...
From $157 per night (USD)VRBO
- From $893 per night (USD)
VRBO
Deep in the Heart of Annapolis; Parking for days!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $893 per night (USD)VRBO
- Click For Pricing
Expedia
New Listing! Walk to USNA\/Capitol\/Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
Click For PricingExpedia
- From $260 per night (USD)
VRBO
Historic Annapolis Home 1.5 blocks from center of town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $260 per night (USD)VRBO
- From $440 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 $440 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $275 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $339 per night (USD)Expedia
- Click For Pricing
VRBO
Indoor Soft Hot Tub - Family Stay @ The Cape!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...
Click For PricingVRBO
- From $394 per night (USD)
Expedia
Nice | BWI Airport | WIFI | 5 BDR | 3 BATH | Baltimore | Casino | 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 $394 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Downtown Annapolis Condo w\/ Free Parking + Coffee
- 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 $159 per night (USD)VRBO
- From $436 per night (USD)
Expedia
Quiet Home Close to Downtown Annapolis and Parks
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...
From $436 per night (USD)Expedia
- From $800 per night (USD)
VRBO
West Annapolis Cottage
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
CONTACT OWNER FOR CW2024/2025 RATES/BOOKING! Recently renovated, this is the perfect location for your family & friends ...
From $800 per night (USD)VRBO
- From $209 per night (USD)
VRBO
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Modern three-bedroom, two full bath home with half-bath and new furnishings. Quiet neighborhood easily accessible to Sa ...
From $209 per night (USD)VRBO
- From $875 per night (USD)
VRBO
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)VRBO
- From $280 per night (USD)
Expedia
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of Annapolis' historic district sits this one bedroom, 1.5 bath cozy apartment. A mere stone's thr ...
From $280 per night (USD)Expedia
- From $800 per night (USD)
VRBO
WATERFRONT Historic Home on the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $800 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
- Click For Pricing
VRBO
Annapolis House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For PricingVRBO
- From $325 per night (USD)
Expedia
Harbor Breezes at Herrington Harbor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $325 per night (USD)Expedia
- 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
- From $222 per night (USD)
VRBO
Annapolis Garden Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, co ...
From $222 per night (USD)VRBO
- From $242 per night (USD)
VRBO
Cheerful 3 bedroom home with ample space and parking on premise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Find your next home away from home in our “Mini Manor”. Enjoy room to spare with 3 bedrooms, two bathrooms, a kitchen w ...
From $242 per night (USD)VRBO
- From $223 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 $223 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 $383 per night (USD)
Expedia
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $383 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Still Available for 2024 Commissioning Week! Historic gem steps to USNA
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $476 per night (USD)VRBO
- From $417 per night (USD)
Expedia
Charming 4BR 2BA w\/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Come stay at this fully updated cozy 4-bedroom 2-bathroom home. Conveniently located with a .6 mile walk to the Naval Ac ...
From $417 per night (USD)Expedia
- From $192 per night (USD)
VRBO
Annapolis Tree House Apartment- luxury shower, separate space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $192 per night (USD)VRBO
- From $367 per night (USD)
Expedia
Free Parking at Admiral's Retreat, 1 mile to Stadium, Backyard, all on one level
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this completely renovated midcentury ranch Annapolis home, jut a mile from the Naval Academy Football Stadium ...
From $367 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Free parking Historic Union House Downtown with private patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly res ...
From $318 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Pet Friendly! River Cottage for 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This adorable cottage sits on 3 picturesque acres overlooking the Magothy River. The charming, newly-furnished River Co ...
From $225 per night (USD)Expedia
- From $445 per night (USD)
VRBO
💥Your Annapolis Retreat near the beach and downtown💥
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to our recently renovated retreat in Annapolis. The place is located minutes from downtown, in the neighborhood ...
From $445 per night (USD)VRBO
- From $369 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 $369 per night (USD)VRBO
- From $258 per night (USD)
VRBO
Club Carp North Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Renovated throughout with three bedrooms and two full baths. This kid-friendly home has a large fenced yard with a swing ...
From $258 per night (USD)VRBO
- From $310 per night (USD)
Expedia
Large Home with Pool & 7 bedrooms; sleeps 21
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in ...
From $310 per night (USD)Expedia
- From $493 per night (USD)
VRBO
Waterfront Annapolis Home: Fire Pit & Fishing Pier
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Meridith Creek, which flows out to Whitehall and Chesapeake Bays, this charming vacation rental features a la ...
From $493 per night (USD)VRBO
- Click For Pricing
Expedia
Cheerful 1 bedroom w pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy one bedroom with pool outdoor eating space and expansive yard for the kids to play in. Private bedroom, bathroom, a ...
Click For PricingExpedia
- Click For Pricing
VRBO
New Townhome\/Room!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Owner and dog live in townhome. Seeking short rentals only. Spacious one bedroom with private bath for professionals see ...
Click For PricingVRBO
- From $626 per night (USD)
VRBO
Charming Romantic, or Navy Professional Historic Retreat—Steps to City Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our historic home in downtown Annapolis! Enjoy your morning coffee on the front porch and host a BBQ in our ...
From $626 per night (USD)VRBO
- Click For Pricing
VRBO
Charming 2 Br in the heart of Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated 2 Bedroom/ 2Bathroom Condo / Full Laundry Central Air Close to: USNA Downtown Annapolis Annapolis Towne Centr ...
Click For PricingVRBO
- From $510 per night (USD)
VRBO
Private pier by Kurtz Beach pet-friendly Dock of the Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to this home on a stunning peninsula with expansive views of the Chesapeake Bay from the kitchen, family room, l ...
From $510 per night (USD)VRBO