search location
Travel Dates:
Reset Dates
307 Rentals In Annapolis
United States
Maryland
Anne Arundel Area
Annapolis
Filters
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
5
3.0
10
Annapolis Maryland Private vacation home
From $577 per night
(USD)
Cozy 2br home w/ parking in downtown Annapolis
2
1.0
6
Annapolis Maryland Private vacation home
From $443 per night
(USD)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
2
1.0
6
Annapolis Maryland Guest house
From $335 per night
(USD)
Charming garden row home, easy 4 block walk to the heart of Annapolis.
3
1.0
6
Annapolis Maryland Private vacation home
From $394 per night
(USD)
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
3
2.0
6
Annapolis Maryland Private vacation home
From $640 per night
(USD)
Historic Capital Views, w Free Off-Site Parking & Patio
3
2.0
8
Annapolis Maryland Private vacation home
From $630 per night
(USD)
Walkable to Main Street at Seashell in the City with 2 parking spots
4
2.0
8
Annapolis Maryland Private vacation home
From $653 per night
(USD)
Anchor's Away in the Heart of Eastport!
1
1.0
3
Annapolis Maryland Apartment
Click For Pricing
Cozy 1st Floor King George one bedroom apartment right across from USNA
1
1.0
4
Annapolis Maryland Apartment
From $247 per night
(USD)
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
2
1.0
6
Annapolis Maryland Apartment
From $400 per night
(USD)
Charming Downtown 3rd Floor 1 Bedroom Apt
1
1.0
4
Annapolis Maryland Apartment
From $241 per night
(USD)
Beautiful Downtown Annapolis Townhome!
3
3.0
8
Annapolis Maryland Private vacation home
From $1010 per night
(USD)
Eastport Cottage .5 mi from Downtown Annapolis
2
1.0
3
Annapolis Maryland Private vacation home
From $599 per night
(USD)
Walk to USNA, Main St w Parking Historic Wisteria
3
4.0
8
Annapolis Maryland Private vacation home
From $629 per night
(USD)
\"Around the Corner\" from Eastport Hot Spots with Fenced-In Yard and Parking
3
2.0
8
Annapolis Maryland Private vacation home
From $613 per night
(USD)
Walk to Waterfront from Eastport Gem w Fire Pit, Porch & Fenced-In Yard
2
1.0
7
Annapolis Maryland Private vacation home
From $559 per night
(USD)
New Downtown Annapolis Condo With Free Parking
2
2.0
4
Annapolis Maryland Condo
From $291 per night
(USD)
Spectacular Location: State Circle Apartment
2
2.0
7
Annapolis Maryland Apartment
From $539 per night
(USD)
Eastport Historic Firehouse with Parking, Dogs OK
2
3.0
8
Annapolis Maryland Private vacation home
From $613 per night
(USD)
Annapolis Condominium in the heart of the historic center
3
2.0
6
Annapolis Maryland Condo
From $383 per night
(USD)
Parking at Randall House Across from USNA Gate 1
4
4.0
11
Annapolis Maryland Private vacation home
From $882 per night
(USD)
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
4
3.0
7
Annapolis Maryland Private vacation home
From $494 per night
(USD)
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
2
1.0
6
Annapolis Maryland Apartment
From $491 per night
(USD)
Historic Chapel Views, Steps to USNA Gate 1 w Private Patio & Off-Site Parking
3
2.0
7
Annapolis Maryland Private vacation home
From $647 per night
(USD)
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
3
2.0
10
Annapolis Maryland Private vacation home
From $633 per night
(USD)
Historic Hanover House Across from USNA Gate 3 w Private Patio
3
2.0
8
Annapolis Maryland Private vacation home
From $625 per night
(USD)
Bay View Studio Apartment
1
1.0
4
Annapolis Maryland Apartment
From $388 per night
(USD)
ACROSS FROM STADIUM - walk to downtown Annapolis.
4
3.0
10
Annapolis Maryland Private vacation home
From $532 per night
(USD)
Prime Location Modern Comfort 1 Block to Gate 1 w Bar & Parking
3
2.0
12
Annapolis Maryland Private vacation home
From $890 per night
(USD)
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
2
2.0
5
Annapolis Maryland Private vacation home
From $716 per night
(USD)
Beautiful Condo - Water View Near City Dock
1
1.0
4
Annapolis Maryland Condo
From $302 per night
(USD)
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
3
3.0
8
Annapolis Maryland Private vacation home
From $629 per night
(USD)
Charming Charles -Walkable Downtown Annapolis Home
2
2.0
6
Annapolis Maryland Private vacation home
From $411 per night
(USD)
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
3
2.0
8
Annapolis Maryland Private vacation home
From $578 per night
(USD)
Cute bungalow blocks to Stadium
2
1.0
6
Annapolis Maryland Private vacation home
From $526 per night
(USD)
Dog friendly! Next to Navy Stadium and DTA Shuttle!
2
1.0
6
Annapolis Maryland Private vacation home
From $547 per night
(USD)
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.
3
2.0
5
Annapolis Maryland Private vacation home
From $420 per night
(USD)
Downtown Pinkney House w/Parking
2
2.0
4
Annapolis Maryland Private vacation home
From $485 per night
(USD)
Historic Annapolis Home!
2
1.0
6
Annapolis Maryland Private vacation home
From $564 per night
(USD)
Maryland Inn 2 Double Beds | Historic Inns | 0.3 Mi to Naval Academy
1
1.0
4
Annapolis Maryland Hotel
From $189 per night
(USD)
Real Maryland Unit | 0.3 Mi to Banneker-Douglass Museum | Steps to State Capitol
1
1.0
4
Annapolis Maryland Hotel
From $189 per night
(USD)
2 Maryland Units | Perfect for Historic Getaways | Pets are Allowed
2
2.0
8
Annapolis Maryland Hotel
From $370 per night
(USD)
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
1
1.0
2
Annapolis Maryland Hotel
From $189 per night
(USD)
Maryland Inn 2 Doubles | Pet-Friendly | 2 Units
2
2.0
8
Annapolis Maryland Hotel
From $367 per night
(USD)
2 Maryland Inn Units at Historic Inns of Annapolis | Waterfront Vicinity
2
2.0
8
Annapolis Maryland Hotel
From $370 per night
(USD)
Just Steps from Waterfront | Robert Johnson King | 0.3mi to US Naval Academy
1
1.0
2
Annapolis Maryland Hotel
From $197 per night
(USD)
Unique Victorian Stay | Steps from Waterfront | 0.1mi to State House
1
1.0
4
Annapolis Maryland Hotel
From $197 per night
(USD)
Robert Johnson Townhouse | 0.1mi State House | 0.3mi Naval Academy
1
1.0
4
Annapolis Maryland Hotel
From $325 per night
(USD)
Governor Calvert 2 Double Beds | Historic Inns | Near Naval Academy
1
1.0
4
Annapolis Maryland Hotel
From $189 per night
(USD)
Maryland Inn King, Historic Inns, Elegant Dining, Waterfront Proximity
1
1.0
2
Annapolis Maryland Hotel
From $189 per night
(USD)
Robert Johnson 2 Double Beds | Historic Inns | 0.8 miles to Cheston Avenue Wharf
1
1.0
4
Annapolis Maryland Hotel
From $197 per night
(USD)
Robert Johnson Townhouse | 0.2mi to Main Street Shops & 0.3mi to Waterfront
1
1.0
4
Annapolis Maryland Hotel
From $329 per night
(USD)
Robert Johnson King | Historic Inns | Near Top Dining & City Attractions
1
1.0
2
Annapolis Maryland Hotel
From $197 per night
(USD)
Charming Downtown Hotel Room w/ Vintage Character + Historic Site
1
1.0
4
Annapolis Maryland Hotel
From $189 per night
(USD)
Elegant Boutique Hotel Near Maryland State House - Short Walk
1
1.0
2
Annapolis Maryland Hotel
From $189 per night
(USD)
2 Historic Ambiance Stays for Perfect Getaways | Pets Are Allowed
2
2.0
8
Annapolis Maryland Hotel
From $367 per night
(USD)
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
2
1.0
6
Annapolis Maryland Private vacation home
From $354 per night
(USD)
Walk to Everything - Historic Art’s District
2
1.0
6
Annapolis Maryland Cottage
From $522 per night
(USD)
Steps to USNA Gate 3, On-Site Parking & Private Patio at Historic Gatehouse
5
4.0
10
Annapolis Maryland Private vacation home
From $824 per night
(USD)
Spacious Converted Carriage House in Historic District near USNA
4
3.0
8
Annapolis Maryland Private vacation home
From $1943 per night
(USD)
Historic Suite 2 Blocks from Main St with On-Site Parking & Dog-Friendly
2
1.0
6
Annapolis Maryland Apartment
From $625 per night
(USD)
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
1
1.0
5
Annapolis Maryland Private vacation home
From $428 per night
(USD)
Historic dog-friendly home 2 blocks to Main St
1
1.0
4
Annapolis Maryland Apartment
From $574 per night
(USD)
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
3
3.0
8
Annapolis Maryland Private vacation home
From $846 per night
(USD)
Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
3
3.0
12
Annapolis Maryland Private vacation home
From $1056 per night
(USD)
Mins to DTA - King Beds - Parking
3
2.0
6
Annapolis Maryland Private vacation home
From $692 per night
(USD)
Steps to Marinas & Shops w Parking in Eastport
2
1.0
6
Annapolis Maryland Private vacation home
From $595 per night
(USD)
Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard
4
2.0
9
Annapolis Maryland Private vacation home
From $598 per night
(USD)
Heart of Annapolis King George Home Steps to USNA Gate 1 & Main Street
2
1.0
6
Annapolis Maryland Private vacation home
From $588 per night
(USD)
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
3
2.0
7
Annapolis Maryland Private vacation home
From $696 per night
(USD)
Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home
3
2.0
6
Annapolis Maryland Private vacation home
From $511 per night
(USD)
Beautiful Historic Flat next to City Dock + USNA
3
1.0
7
Annapolis Maryland Private vacation home
From $710 per night
(USD)
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
4
3.0
12
Annapolis Maryland Private vacation home
From $709 per night
(USD)
Experience Historic Annapolis Stay in This Unique Dual-Suite Home with On-Site Parking
3
2.0
10
Annapolis Maryland Private vacation home
From $705 per night
(USD)
Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking
3
3.0
8
Annapolis Maryland Private vacation home
From $632 per night
(USD)
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
3
2.0
6
Annapolis Maryland Private vacation home
From $635 per night
(USD)
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
4
4.0
10
Annapolis Maryland Private vacation home
From $1917 per night
(USD)
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
2
1.0
6
Annapolis Maryland Private vacation home
From $610 per night
(USD)
Historic downtown townhome with brick courtyard, sunroom & parking
3
2.0
6
Annapolis Maryland Private vacation home
From $634 per night
(USD)
Updated historic home with parking; near Academy, college & harbor - central AC
4
2.0
8
Annapolis Maryland Private vacation home
From $1007 per night
(USD)
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
4
3.0
8
Annapolis Maryland Private vacation home
From $747 per night
(USD)
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
4
2.0
10
Annapolis Maryland Private vacation home
From $548 per night
(USD)
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
2
2.0
4
Annapolis Maryland Private vacation home
From $572 per night
(USD)
Waterfront Annapolis Home Near USNA Stadium
3
2.0
6
Annapolis Maryland Private vacation home
From $987 per night
(USD)
Annapolis Charmer - Perfect Location
3
2.0
6
Annapolis Maryland Private vacation home
From $698 per night
(USD)
Unique and central in Eastport
4
3.0
8
Annapolis Maryland Private vacation home
From $428 per night
(USD)
Eastport 4 Bedroom Spacious Gem on Jefferson
4
3.0
8
Annapolis Maryland Private vacation home
From $1249 per night
(USD)
Chapel Gate 3BR Steps to City Dock & Naval Academy
3
1.0
6
Annapolis Maryland Condo
From $515 per night
(USD)
Downtown Annapolis 3 bedroom home with parking!
3
1.0
6
Annapolis Maryland Private vacation home
From $514 per night
(USD)
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4
2.0
10
Annapolis Maryland Private vacation home
From $726 per night
(USD)
Eastport 3 bedroom Cottage: Walk to Downtown
3
2.0
8
Annapolis Maryland Private vacation home
From $751 per night
(USD)
Spacious 4-bedroom house with AC in brilliant Annapolis
4
1.0
6
Annapolis Maryland Private vacation home
From $167 per night
(USD)
Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital
5
1.0
10
Annapolis Maryland Private vacation home
From $506 per night
(USD)
Classic 3 Bedroom Eastport Cottage with Large Yard and Free Parking
3
2.0
6
Annapolis Maryland Private vacation home
From $388 per night
(USD)
5 bedroom house with EV charger Near Downtown Annapolis
5
2.0
12
Annapolis Maryland Private vacation home
From $739 per night
(USD)
Charming, Newly-Renovated Historic Row Home w Private Patio & Parking
3
2.0
6
Annapolis Maryland Private vacation home
From $634 per night
(USD)
Historic Downtown Luxury • USNA • Waterfront
5
3.0
10
Annapolis Maryland Private vacation home
From $1450 per night
(USD)
Elegant 3-bedroom house with EV charger in Downtown Annapolis
3
1.0
6
Annapolis Maryland Private vacation home
From $393 per night
(USD)
Green on Fleet 1 Block to City Dock & USNA w Parking
2
1.0
4
Annapolis Maryland Private vacation home
From $601 per night
(USD)
Charming Living room in beautiful Annapolis with AC discount long stay
1
1.0
2
Annapolis Maryland Bed & breakfast
From $359 per night
(USD)
Load More Results
