Severn River Rentals
- From $350 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 $350 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
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)Expedia
- 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 $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
- From $743 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 $743 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 $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 $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
- 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)
VRBO
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)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
- 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
- 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 $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 $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
- 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 $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 $893 per night (USD)
Expedia
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)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $260 per night (USD)
Expedia
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)Expedia
- 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)
Expedia
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)Expedia
- From $339 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- 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 $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
Expedia
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 PricingExpedia
- 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
- 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 $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
- Click For Pricing
VRBO
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 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
- Click For Pricing
Expedia
New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A brand new, clean pied-a-terre just a walk away from downtown Annapolis! Enjoy Commissioning Week/Blue Angels, Boat Sho ...
Click For PricingExpedia
- 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 $350 per night (USD)
Expedia
Spectacular Location: State Circle Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $350 per night (USD)Expedia
- Click For Pricing
Expedia
Take the water taxi, bike or drive to Downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous, clean, bright house in a great location. About a mile and a half to Downtown Annapolis. Playground around the ...
Click For PricingExpedia
- From $508 per night (USD)
Expedia
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $508 per night (USD)Expedia
- From $406 per night (USD)
VRBO
Available 2024 Commissioning Week 13 mins to USNA Big Family Space
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
**Still available for 2024 Commissioning Week - 5 night minimum! From the moment you walk into this lovely home, you wi ...
From $406 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- Click For Pricing
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 ...
Click For PricingExpedia
- From $1394 per night (USD)
VRBO
Stunning Waterfront Home with Incredible Water Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to your perfect family getaway at this stunning 6,000 square foot waterfront home in Bay Ridge, Annapolis. Nestl ...
From $1394 per night (USD)VRBO
- From $745 per night (USD)
VRBO
NEW, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This clean, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect for families ...
From $745 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Annapolis Condominium in the heart of the historic center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $273 per night (USD)Expedia
- From $330 per night (USD)
VRBO
Chic Condo w\/ Balcony in the Heart of Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
From $330 per night (USD)VRBO
- 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 $445 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 $445 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Charming Historic Townhouse Steps From USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...
From $250 per night (USD)Expedia
- 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 $500 per night (USD)
Expedia
Historic Annapolis Home Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
From $500 per night (USD)Expedia
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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 $549 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 $549 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 $350 per night (USD)
Expedia
Annapolis Downtown Entire Townhome 3 bed 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $350 per night (USD)Expedia
- 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 ...
Click For PricingVRBO
- Click For Pricing
Expedia
Historic Annapolis Home, Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For PricingExpedia
- Click For Pricing
VRBO
Modern Comfort in Great Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A beautiful new 3-level town home in gated community: stainless steel appliances, hardwood floors, indoor/outdoor firepl ...
Click For PricingVRBO
- From $1021 per night (USD)
Expedia
Free Parking at Randall House in Downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1021 per night (USD)Expedia
- Click For Pricing
VRBO
Eastport Hideaway - Perfect little guesthouse for 2
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Welcome to our newest listing in Annapolis . Tucked away is this sweet little guesthouse that has been newly renovated . ...
Click For PricingVRBO
- From $1300 per night (USD)
Expedia
5 BDRM across from the USNA Stadium
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
From $1300 per night (USD)Expedia
- From $1375 per night (USD)
VRBO
Stunning Waterfront Home in Round Bay
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Available for Boat Shows! Ask us about the option to add on the 5th bedroom. This beautiful home with unobstructed view ...
From $1375 per night (USD)VRBO
- From $570 per night (USD)
Expedia
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Our quiet 3 bed 2.5 bath home is the perfect Annapolis getaway! On a dead end road. A quick walk to the best downtown r ...
From $570 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Adorable home steps from Navy Stadium!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $375 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 $252 per night (USD)
VRBO
Eastport Bungalow - Popular house Walk to Downtown & USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
*Flexible Commissioning Week Cancellation Policy* This unique built in 1927, is a classic Bungalow with historic charm. ...
From $252 per night (USD)VRBO
- From $216 per night (USD)
Expedia
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Five blocks to Naval Bagels, Agave, Chessie's Wharf, Evelyn's, Bean Rush Cafe, Rutabagas, Grauls Groceries and other sho ...
From $216 per night (USD)Expedia
- Click For Pricing
VRBO
Spacious home with outdoor fireplace & fenced yard with outdoor kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Stone's Throw Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingVRBO
- From $417 per night (USD)
Expedia
Riverfront home with multiple decks, central AC, washer\/dryer - two dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Chase Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $417 per night (USD)Expedia
- From $1008 per night (USD)
VRBO
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 15
Bella Chateau Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1008 per night (USD)VRBO
- From $727 per night (USD)
Expedia
Newly renovated downtown home with patio, gas grill, and gas fireplace
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $727 per night (USD)Expedia