Annapolis Rentals
From $577 per night (USD)VRBO
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $577 per night (USD)VRBO
From $443 per night (USD)Expedia
Cozy 2br home w/ parking in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $443 per night (USD)Expedia
From $640 per night (USD)VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $640 per night (USD)VRBO
From $630 per night (USD)Expedia
Historic Capital Views, w Free Off-Site Parking & Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Experience Historic Annapolis in Comfort and Style ...
From $630 per night (USD)Expedia
From $653 per night (USD)VRBO
Walkable to Main Street at Seashell in the City with 2 parking spots
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this gorgeous fully-renovated home, res ...
From $653 per night (USD)VRBO
Click For PricingExpedia
Anchor's Away in the Heart of Eastport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
Click For PricingExpedia
From $247 per night (USD)VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $247 per night (USD)VRBO
From $241 per night (USD)Expedia
Charming Downtown 3rd Floor 1 Bedroom Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park y ...
From $241 per night (USD)Expedia
From $1010 per night (USD)VRBO
Beautiful Downtown Annapolis Townhome!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $1010 per night (USD)VRBO
From $599 per night (USD)Expedia
Eastport Cottage .5 mi from Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, t ...
From $599 per night (USD)Expedia
From $629 per night (USD)VRBO
Walk to USNA, Main St w Parking Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis How many homes in Downtown Annapolis have 4 Bedroo ...
From $629 per night (USD)VRBO
From $613 per night (USD)Expedia
\"Around the Corner\" from Eastport Hot Spots with Fenced-In Yard and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Still available for Commissioning Week 2025! ...
From $613 per night (USD)Expedia
From $559 per night (USD)VRBO
Walk to Waterfront from Eastport Gem w Fire Pit, Porch & Fenced-In Yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis Walk to waterfront restaurants, hop the water taxi ...
From $559 per night (USD)VRBO
From $291 per night (USD)Expedia
New Downtown Annapolis Condo With Free Parking
- 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 $291 per night (USD)Expedia
From $494 per night (USD)VRBO
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $494 per night (USD)VRBO
From $539 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 $539 per night (USD)Expedia
From $613 per night (USD)VRBO
Eastport Historic Firehouse with Parking, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis This is a unique home like none other in downtown ...
From $613 per night (USD)VRBO
From $383 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 $383 per night (USD)Expedia
From $882 per night (USD)VRBO
Parking at Randall House Across from USNA Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Experience the Difference: Professionally Managed by iTrip Annapolis The Randall House is an historic gem in the heart ...
From $882 per night (USD)VRBO
From $491 per night (USD)Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street p ...
From $491 per night (USD)Expedia
From $647 per night (USD)VRBO
Historic Chapel Views, Steps to USNA Gate 1 w Private Patio & Off-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis When the owners decided to find their Annapolis ho ...
From $647 per night (USD)VRBO
From $633 per night (USD)Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 2
- 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 $633 per night (USD)Expedia
From $625 per night (USD)VRBO
Historic Hanover House Across from USNA Gate 3 w Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis The fully-renovated 1800 historic home is just ste ...
From $625 per night (USD)VRBO
From $388 per night (USD)Expedia
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 ...
From $388 per night (USD)Expedia
From $532 per night (USD)VRBO
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 ...
From $532 per night (USD)VRBO
From $890 per night (USD)Expedia
Prime Location Modern Comfort 1 Block to Gate 1 w Bar & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Modern Elegance in Historic Annapolis ...
From $890 per night (USD)Expedia
From $716 per night (USD)VRBO
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 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $716 per night (USD)VRBO
From $629 per night (USD)VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Skridt fra Annapolis By Dock og US Naval Academy- gåtur til alle butikker, restauranter og downtown begivenheder. Denne ...
From $629 per night (USD)VRBO
From $302 per night (USD)VRBO
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $302 per night (USD)VRBO
From $411 per night (USD)Expedia
Charming Charles -Walkable Downtown Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to your private oasis in this stylish 2-bed, 2.5-bath townhome in the heart of Downtown Annapolis. This ...
From $411 per night (USD)Expedia
From $578 per night (USD)VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
- Bedrooms:
- 2
- 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 $578 per night (USD)VRBO
From $547 per night (USD)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 ...
From $547 per night (USD)Expedia
From $189 per night (USD)VRBO
Maryland Inn 2 Double Beds | Historic Inns | 0.3 Mi to Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Real Maryland Unit | 0.3 Mi to Banneker-Douglass Museum | Steps to State Capitol
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $370 per night (USD)VRBO
2 Maryland Units | Perfect for Historic Getaways | Pets are Allowed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $370 per night (USD)VRBO
From $189 per night (USD)VRBO
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $367 per night (USD)VRBO
Maryland Inn 2 Doubles | Pet-Friendly | 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $367 per night (USD)VRBO
From $370 per night (USD)VRBO
2 Maryland Inn Units at Historic Inns of Annapolis | Waterfront Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $370 per night (USD)VRBO
From $197 per night (USD)VRBO
Just Steps from Waterfront | Robert Johnson King | 0.3mi to US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $197 per night (USD)VRBO
Unique Victorian Stay | Steps from Waterfront | 0.1mi to State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $325 per night (USD)VRBO
Robert Johnson Townhouse | 0.1mi State House | 0.3mi Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $325 per night (USD)VRBO
From $189 per night (USD)VRBO
Governor Calvert 2 Double Beds | Historic Inns | Near Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Maryland Inn King, Historic Inns, Elegant Dining, Waterfront Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $197 per night (USD)VRBO
Robert Johnson 2 Double Beds | Historic Inns | 0.8 miles to Cheston Avenue Wharf
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $329 per night (USD)VRBO
Robert Johnson Townhouse | 0.2mi to Main Street Shops & 0.3mi to Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $329 per night (USD)VRBO
From $197 per night (USD)VRBO
Robert Johnson King | Historic Inns | Near Top Dining & City Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $189 per night (USD)VRBO
Charming Downtown Hotel Room w/ Vintage Character + Historic Site
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Elegant Boutique Hotel Near Maryland State House - Short Walk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $367 per night (USD)VRBO
2 Historic Ambiance Stays for Perfect Getaways | Pets Are Allowed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $367 per night (USD)VRBO
From $354 per night (USD)Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $354 per night (USD)Expedia
From $522 per night (USD)VRBO
Walk to Everything - Historic Art’s District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $522 per night (USD)VRBO
From $1943 per night (USD)Expedia
Spacious Converted Carriage House in Historic District near USNA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1943 per night (USD)Expedia
From $625 per night (USD)VRBO
Historic Suite 2 Blocks from Main St with On-Site Parking & Dog-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Still available for Commissioning Week 2025! ...
From $625 per night (USD)VRBO
From $428 per night (USD)Expedia
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $428 per night (USD)Expedia
From $846 per night (USD)VRBO
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $846 per night (USD)VRBO
From $692 per night (USD)Expedia
Mins to DTA - King Beds - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $692 per night (USD)Expedia
From $595 per night (USD)VRBO
Steps to Marinas & Shops w Parking in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Eastport's Third Time's the Charm – Steps from Mar ...
From $595 per night (USD)VRBO
From $598 per night (USD)Expedia
Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis A new home but managed by experienced hosts, iTrip ...
From $598 per night (USD)Expedia
From $588 per night (USD)VRBO
Heart of Annapolis King George Home Steps to USNA Gate 1 & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Your Historic Annapolis Retreat! Disc ...
From $588 per night (USD)VRBO
From $696 per night (USD)Expedia
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $696 per night (USD)Expedia
From $710 per night (USD)VRBO
Beautiful Historic Flat next to City Dock + USNA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis ...
From $710 per night (USD)VRBO
From $705 per night (USD)Expedia
Experience Historic Annapolis Stay in This Unique Dual-Suite Home with On-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Stay right in the heart of Historic Annapolis, jus ...
From $705 per night (USD)Expedia
From $709 per night (USD)VRBO
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Mar ...
From $709 per night (USD)VRBO
From $632 per night (USD)Expedia
Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Step into Annapolis history at this beautifully re ...
From $632 per night (USD)Expedia
From $388 per night (USD)VRBO
Classic 3 Bedroom Eastport Cottage with Large Yard and Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the perfect Annapolis getaway in this charming three bedroom Eastport cottage. Ideally located just ...
From $388 per night (USD)VRBO
From $1917 per night (USD)Expedia
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience ...
From $1917 per night (USD)Expedia
From $610 per night (USD)VRBO
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, a ...
From $610 per night (USD)VRBO
From $634 per night (USD)Expedia
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and ...
From $634 per night (USD)Expedia
From $1007 per night (USD)VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, an ...
From $1007 per night (USD)VRBO
From $747 per night (USD)Expedia
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this tw ...
From $747 per night (USD)Expedia
From $548 per night (USD)VRBO
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great wa ...
From $548 per night (USD)VRBO
From $572 per night (USD)Expedia
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis' cha ...
From $572 per night (USD)Expedia
From $987 per night (USD)VRBO
Waterfront Annapolis Home Near USNA Stadium
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your waterfront Annapolis getaway! This inviting 3-bedroom home comfortably sleeps 6 and offers pea ...
From $987 per night (USD)VRBO
From $698 per night (USD)Expedia
Annapolis Charmer - Perfect Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy a stylish stay in this beautifully updated, centrally located home featuring brand-new furnishings and a ...
From $698 per night (USD)Expedia
From $515 per night (USD)VRBO
Chapel Gate 3BR Steps to City Dock & Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Chapel Gate! Ideally located just outside Gate 3 of the U.S. Naval Academy and only a few blocks fr ...
From $515 per night (USD)VRBO
From $726 per night (USD)Expedia
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Relax after a fun Annapolis day in this well-appointed and spacious home. Centrally located in peaceful Murray ...
From $726 per night (USD)Expedia
From $739 per night (USD)VRBO
5 bedroom house with EV charger Near Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Experience coastal charm and modern comfort at Voyagers’ Nest, a spacious 5-bedroom retreat near downtown Annapolis and ...
From $739 per night (USD)VRBO
From $601 per night (USD)Expedia
Green on Fleet 1 Block to City Dock & USNA w Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis Green on Fleet – Historic Annapolis Rowhouse (c.18 ...
From $601 per night (USD)Expedia
From $359 per night (USD)VRBO
Charming Living room in beautiful Annapolis with AC discount long stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Popular Annapolis, tents for $4000/night deeply discounted this bed & breakfast is a dream. Guests will find ...
From $359 per night (USD)VRBO
From $139 per night (USD)Expedia
Charming barn in Annapolis for a relaxing getaway not a room just a mattress
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to this awesome barn in picturesque Annapolis. Guests enjoy a welcoming space featuring a cozy bathroom with a re ...
From $139 per night (USD)Expedia
From $640 per night (USD)VRBO
Two Historic Rowhomes in Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Two connected, historic row homes in the heart of Downtown Annapolis! Perfect for two families or larger group ...
From $640 per night (USD)VRBO
From $1252 per night (USD)Expedia
Luxe Row Home Steps to USNA Gate 3!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience a beautifully restored and well appointed Greek Revival home on a calm street directly facing the U ...
From $1252 per night (USD)Expedia
From $639 per night (USD)VRBO
Walk To Main St & City Dock from Historic Downtown Dog-Friendly Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Historic Downtown Annapolis Apartment | Dog-Friend ...
From $639 per night (USD)VRBO
From $412 per night (USD)Expedia
Historic Annapolis Home Walk to Downtown 3BR
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Stay in the heart of Annapolis in this beautifully restored historic home just a 5-minute walk from downtown. ...
From $412 per night (USD)Expedia
From $940 per night (USD)VRBO
Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NEWLY RENOVATED ENSUITE MASTER BATHROOM! Experience the perfect blend of historic Annapolis charm and modern comfort i ...
From $940 per night (USD)VRBO
From $741 per night (USD)VRBO
The Liberty House - Pristine Reno with parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Liberty House ! This pristine home in the Murray Hill section of downtown Annapolis is sure to check all you ...
From $741 per night (USD)VRBO
From $514 per night (USD)VRBO
Eastport Cottage Only 4 Blocks to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the best of Annapolis from this charming and beautifully updated home in the desirable Eastport neighborhood. Loca ...
From $514 per night (USD)VRBO
From $455 per night (USD)VRBO
DTA Row Home | Walk to City Dock & The Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay on one of Annapolis's most iconic streets in this renovated 3-level row home. Walk out the door and you'r ...
From $455 per night (USD)VRBO
From $516 per night (USD)VRBO
Cozy Townhome in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Modern Downtown Annapolis Retreat – Walk to Everything Welcome to 222 West Street – Unit A, a thoughtfully designed pri ...
From $516 per night (USD)VRBO
From $958 per night (USD)VRBO
Charming Annapolis Escape!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This Charming Annapolis property features 2 king beds and 2 queen beds; 2 living areas complete with large TVs. The Kitc ...
From $958 per night (USD)VRBO
From $1924 per night (USD)VRBO
Submariner's Gate - Historic 4-bedroom home in charming Annapolis with parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Step into Annapolis history at this lovingly restored 1867 home — said to be the first subdivision of the Hammond-Harwoo ...
From $1924 per night (USD)VRBO
From $535 per night (USD)VRBO
Charming Rowhome in Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church a ...
From $535 per night (USD)VRBO
- From $619 per night (USD)
VRBO
Walk to everything! Downtown Historic Annapolis “Arts District”
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
None delete delete delete delete delete delete delete delete delete delete delete delete delete deletebbbbbbvvvvvvvvvggg ...
From $619 per night (USD)VRBO
From $374 per night (USD)VRBO
West Annapolis Cottage | Porch, Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Bright, renovated, and perfectly positioned. This West Annapolis cottage has a screened porch for lazy morning ...
From $374 per night (USD)VRBO
From $674 per night (USD)VRBO
Modern Styled Home in Historic Annapolis Eastport Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $674 per night (USD)VRBO
From $1032 per night (USD)VRBO
Beautiful Historic Annapolis home just a few minutes walk from Main Street
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming Historic Annapolis Candlelight and Secret Garden tour home, built in 1879, with gorgeous heart pine floors. Cus ...
From $1032 per night (USD)VRBO
From $744 per night (USD)VRBO
Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
RENT-005995-2024-The Campbell House on Prince George offers the best of downtown Annapolis with a rare blend of historic ...
From $744 per night (USD)VRBO
From $577 per night (USD)VRBO
Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Yes! It really is the Perfect Vacation Rental in Annapolis!----Discover the perfect blend of historic charm and contemp ...
From $577 per night (USD)VRBO
From $462 per night (USD)VRBO
Historic District 2BR + Parking | Walk to City Dock & USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Stay in the heart of Annapolis’ Historic District, just a short walk from City Dock, the U.S. Naval Academy, restaurants ...
From $462 per night (USD)VRBO
From $522 per night (USD)VRBO
Historic Downtown Annapolis | 2BR En Suites | Walk to USNA & City Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in the heart of historic downtown Annapolis at this charming 2-bedroom, 2.5-bath townhome on quiet Pinkney Street. ...
From $522 per night (USD)VRBO