Holiday Rentals near Annapolis Historic District
Main Street, Annapolis, Maryland 21401
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
353 rentals in Annapolis.
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Holiday Rental House
8.7 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Condo/Apartment
0.8 kilometres from Annapolis Historic District
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
Holiday Rental House
0.5 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Upscale home with parking for 4 cars in driveway. Walk to downtown.
Holiday Rental House
1.0 kilometres from Annapolis Historic District
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
Holiday Rental House
1.4 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Condo/Apartment
0.5 kilometres from Annapolis Historic District
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Cozy place close to the city dock
Condo/Apartment
3.7 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Historic Downtown Charmer, Water Views and Parking!
Holiday Rental House
0.3 kilometres from Annapolis Historic District
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
West Annapolis Waterfront Stay with Views, Dock & Boat
Condo/Apartment
1.6 kilometres from Annapolis Historic District
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
3 Story Stunner in Murray Hill <1 mile from USNA!
Holiday Rental House
0.5 kilometres from Annapolis Historic District
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Historic District Charm with two mid-size or smaller parking spots!
Holiday Rental House
0.3 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Cozy 1st Floor King George one bedroom apartment right across from USNA
Condo/Apartment
0.5 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
ACROSS FROM STADIUM - walk to downtown Annapolis.
Holiday Rental House
1.6 kilometres from Annapolis Historic District
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Holiday Rental House
1.6 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Renovated Historic Home located downtown with parking - Walk everywhere !
Holiday Rental House
0.3 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Annapolis Condominium in the heart of the historic center
Condo/Apartment
0.2 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stunning Waterfront Cottage with Breathtaking Views!
Holiday Rental House
1.9 kilometres from Annapolis Historic District
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
PERFECT LOCATION in the heart of history
Holiday Rental House
0.5 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charming Annapolis WaterVIEW Home
Holiday Rental House
6.9 kilometres from Annapolis Historic District
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Holiday Rental House
1.1 kilometres from Annapolis Historic District
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charming Historic Annapolis Home With Two Off-street Parking Places!
Holiday Rental House
0.5 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Heart of Historic District!
Holiday Rental House
0.3 kilometres from Annapolis Historic District
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard
Holiday Rental House
1.3 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Happy days on the Bay at dog-friendly beachfront home on the Chesapeake
Holiday Rental House
2.1 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Yellow Cottage on Harness Creek
Holiday Rental House
4.5 kilometres from Annapolis Historic District
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Condo/Apartment
5.6 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
Holiday Rental House
0.8 kilometres from Annapolis Historic District
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
As seen on
Bay View Studio Apartment
Condo/Apartment
2.1 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Freshly renovated 3-story home 1 block from USNA!
Holiday Rental House
0.3 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Condo/Apartment
1.6 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Your Annapolis adventure starts here!!
Holiday Rental House
2.9 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Condo/Apartment
0.5 kilometres from Annapolis Historic District
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Holiday Rental House
0.5 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
La Maison - Stunning waterfront views with pool
Holiday Rental House
6.6 kilometres from Annapolis Historic District
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
New rates! Historic happy home, steps to Main Street, parking and lots of
Holiday Rental House
0.2 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Condo/Apartment
1.1 kilometres from Annapolis Historic District
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Waterfront Oasis in Eastport - Walk to Downtown and USNA
Holiday Rental House
0.8 kilometres from Annapolis Historic District
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Little Magothy Riverfront Home With Pool
Holiday Rental House
8.9 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Holiday Rental House
1.3 kilometres from Annapolis Historic District
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Downtown Annapolis Townhome ! Beautiful!!
Holiday Rental House
0.3 kilometres from Annapolis Historic District
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Location Location Location!!!50 Steps from Main Street and all of the action
Holiday Rental House
0.2 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic
Holiday Rental House
0.2 kilometres from Annapolis Historic District
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Welcome Aboard the Kathleen Marie!
Holiday Rental House
1.6 kilometres from Annapolis Historic District
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Chic Condo w/ Balcony in the Heart of Annapolis!
Condo/Apartment
0.5 kilometres from Annapolis Historic District
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
New Rates! Modern and cozy Captain’s Crossing Cape house in West Annapolis
Holiday Rental House
1.8 kilometres from Annapolis Historic District
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
NEW! Waterfront Annapolis Getaway w / Fishing Pier!
Holiday Rental House
7.6 kilometres from Annapolis Historic District
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Condo/Apartment
1.6 kilometres from Annapolis Historic District
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Nautical Feel to This Beautiful Eastport Home
Holiday Rental House
1.1 kilometres from Annapolis Historic District
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Holiday Rental House
0.5 kilometres from Annapolis Historic District
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
Holiday Rental House
2.1 kilometres from Annapolis Historic District
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 353
Annapolis TourismAnnapolis AccommodationAnnapolis Holiday RentalsAnnapolis FlightsAnnapolis RestaurantsAnnapolis AttractionsAnnapolis Travel ForumAnnapolis PhotosAnnapolis MapAnnapolis Guide
All Annapolis HotelsAnnapolis Hotel DealsLast Minute Hotels in Annapolis
Things to DoRestaurantsFlightsHoliday RentalsTravel StoriesCruisesRental CarsAnnapolis MotelsFamily Hotels AnnapolisBusiness Hotels AnnapolisAnnapolis Green HotelsRomantic Hotels AnnapolisLuxury Hotels Annapolis
Choice Hotels in AnnapolisMarriott Hotels in AnnapolisInterContinental (IHG) Hotels in AnnapolisHilton Hotels in AnnapolisHilton Garden Inns in Annapolis
Annapolis Exotic HotelsAnnapolis Hotels with Bike RentalsAnnapolis Hotels with Allergy-free RoomsAnnapolis Hotels with EV ChargingAnnapolis Hotels with Breakfast BuffetAnnapolis Hotels with Heated PoolAnnapolis Adventure HotelsAnnapolis Hotels with Banquet HallAnnapolis Hotels with Bridal SuiteAnnapolis Hotels with Valet Parking