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Vacation Rentals
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World
>
USA
>
Maryland
>
Annapolis
3
BR /
2
BA /
Sleeps
8
Featured
4
BR /
4
BA /
Sleeps
14
From $500/nt
Featured
4
BR /
2
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Sleeps
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BR /
2
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Sleeps
11
From $500/nt
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BR /
3
BA /
Sleeps
10
From $350/nt
Featured
Annapolis with Fireplace
(78)
sort by
HomeAway Sort
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Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
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Price: Low to High
Number of Reviews
Special Offers First
Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views!
3 Bedrooms,
3
Bathrooms
, Sleeps 10
$350 - $500
per night
Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views!
Book it Now!
2 night minimum stay
3
BR,
3
BA,
Sleeps
10
Maryland
>
Annapolis House
#968476
(20)
Compare
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, wifi ,Family/Retreat
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 15
$400 - $975
per night
Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, wifi ,Family/Retreat
Book it Now!
2 - 3 night minimum stay
5
BR,
2
BA,
1
HF BA,
Sleeps
15
Maryland
>
Annapolis House
#223105
(32)
Compare
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
5 Bedrooms,
3
Bathrooms
, Sleeps 20
$495 - $695
per night
Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa!
Book it Now!
2 - 3 night minimum stay
5
BR,
3
BA,
Sleeps
20
Maryland
>
Annapolis Cottage
#390303vb
(24)
Compare
Annapolis Area Severn River Waterfront
5 Bedrooms,
2
Bathrooms
,
2
Half Baths
, Sleeps 11
$500
per night
Annapolis Area Severn River Waterfront
4 night minimum stay
5
BR,
2
BA,
2
HF BA,
Sleeps
11
Maryland
>
Annapolis House
#360959
(10)
Compare
Beautiful Annapolis Getaway - Walk Everywhere!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$300 - $400
per night
Beautiful Annapolis Getaway - Walk Everywhere!
2 night minimum stay
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#461541vb
(9)
Compare
Stunning Downtown Home Steps From the Academy!
3 Bedrooms,
3
Bathrooms
,
2
Half Baths
, Sleeps 9
$750 - $875
per night
Stunning Downtown Home Steps From the Academy!
2 night minimum stay
3
BR,
3
BA,
2
HF BA,
Sleeps
9
Maryland
>
Annapolis House
#345765
(12)
Compare
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4 Bedrooms,
4
Bathrooms
, Sleeps 14
$500 - $1,200
per night
Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
4
BR,
4
BA,
Sleeps
14
Maryland
>
Annapolis House
#241350
(13)
Compare
Renovated Historic Home Located Downtown -Walk Everywhere!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Renovated Historic Home Located Downtown -Walk Everywhere!
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#951256
(28)
Compare
Gorgeous Southern Colonial on the Water in Annapolis-
6 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 16
Gorgeous Southern Colonial on the Water in Annapolis-
6
BR,
4
BA,
1
HF BA,
Sleeps
16
Maryland
>
Annapolis Cottage
#283672
(44)
Compare
Luxurious Historic Home in the Heart of Downtown Annapolis!
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 7
$375 - $475
per night
Luxurious Historic Home in the Heart of Downtown Annapolis!
Book it Now!
2 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
7
Maryland
>
Annapolis House
#173289
(58)
Compare
Wonderful Location! 10% Discounts for select Nov & Dec dates.
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
Wonderful Location! 10% Discounts for select Nov & Dec dates.
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Maryland
>
Annapolis House
#319055
(26)
Compare
Waterfront Relaxing Retreat in Annapolis Area
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$375
per night
Waterfront Relaxing Retreat in Annapolis Area
3 night minimum stay
3
BR,
3
BA,
1
HF BA,
Sleeps
10
Maryland
>
Annapolis House
#432131vb
(11)
Compare
One block from the naval academy entrance!! Historical Annapolis!!
3 Bedrooms,
2
Bathrooms
,
2
Half Baths
, Sleeps 8
$450
per night
One block from the naval academy entrance!! Historical Annapolis!!
Book it Now!
2 night minimum stay
3
BR,
2
BA,
2
HF BA,
Sleeps
8
Maryland
>
Annapolis House
#989211
1 Review
Compare
Oak Bluff - Waterfront on a Peninsula - Private Pier. Great Crabbing - Wi-Fi.
3 Bedrooms,
2
Bathrooms
, Sleeps 7
$250 - $340
per night
Oak Bluff - Waterfront on a Peninsula - Private Pier. Great Crabbing - Wi-Fi.
2 - 3 night minimum stay
3
BR,
2
BA,
Sleeps
7
Maryland
>
Annapolis House
#208564
(11)
Compare
Quiet, Relaxing Waterfront Suisse Chalet with Dock for Boats
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
Quiet, Relaxing Waterfront Suisse Chalet with Dock for Boats
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Maryland
>
Annapolis Chalet
#905951
(5)
Compare
Waterfront 5BR Home - Annapolis/Severna Park
5 Bedrooms, Sleeps 12
Waterfront 5BR Home - Annapolis/Severna Park
5
BR,
Sleeps
12
Maryland
>
Annapolis House
#64039vb
1 Review
Compare
Waterfront Cottage - Chesapeake Bay -Near Annapolis
4 Bedrooms,
2
Bathrooms
, Sleeps 10
$1,950 - $2,600
per week
Waterfront Cottage - Chesapeake Bay -Near Annapolis
2 - 7 night minimum stay
4
BR,
2
BA,
Sleeps
10
Maryland
>
Annapolis Cottage
#211561
(5)
Compare
Waterfront with Stunning Views! Private Pier
Studio, Sleeps 8
$450 - $500
per night
Waterfront with Stunning Views! Private Pier
Book it Now!
2 night minimum stay
Studio,
Sleeps
8
Maryland
>
Annapolis House
#474810vb
Compare
Coastal Cottage Living in Historic Annapolis-Eastport
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$375 - $400
per night
Coastal Cottage Living in Historic Annapolis-Eastport
Book it Now!
2 night minimum stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Maryland
>
Annapolis Cottage
#3490726
Compare
Annapolis Waterfront South River Chesapeake Bay
3 Bedrooms,
3
Bathrooms
, Sleeps 7
$250 - $295
per night
Annapolis Waterfront South River Chesapeake Bay
3 night minimum stay
3
BR,
3
BA,
Sleeps
7
Maryland
>
Annapolis House
#116553
(15)
Compare
Charming Vintage Cottage.Walk to Cafe/Shops/Bay
2 Bedrooms,
1
Bathroom
, Sleeps 8
Charming Vintage Cottage.Walk to Cafe/Shops/Bay
2
BR,
1
BA,
Sleeps
8
Maryland
>
Annapolis Cottage
#909302
(40)
Compare
Walk to Naval Academy Stadium, Only 1.5 Mile to City Dock
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$350
per night
Walk to Naval Academy Stadium, Only 1.5 Mile to City Dock
3 night minimum stay
2
BR,
2
BA,
Sleeps
4
Maryland
>
Annapolis Apartment
#900870
(7)
Compare
Downtown Annapolis for Grad Week, Boat Shows, Entertaining
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
Downtown Annapolis for Grad Week, Boat Shows, Entertaining
3
BR,
3
BA,
1
HF BA,
Sleeps
10
Maryland
>
Annapolis House
#378238
(10)
Compare
'Newer Cottage Incredibly and Comfortably Furnished.'
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$185
per night
'Newer Cottage Incredibly and Comfortably Furnished.'
2 night minimum stay
2
BR,
2
BA,
Sleeps
6
Maryland
>
Annapolis Cottage
#151554
(13)
Compare
Elegant and Luxurious Home facing the Annapolis Harbor
5 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 10
$1,050
per night
Elegant and Luxurious Home facing the Annapolis Harbor
3 night minimum stay
5
BR,
4
BA,
1
HF BA,
Sleeps
10
Maryland
>
Annapolis House
#248720
Compare
Casa Arundel
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Casa Arundel
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#282625
(13)
Compare
Charming Family Size home Walking distance to Everything
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Charming Family Size home Walking distance to Everything
3
BR,
3
BA,
Sleeps
8
Maryland
>
Annapolis House
#266174
Compare
Memories on the Bay
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 14
Memories on the Bay
5
BR,
3
BA,
1
HF BA,
Sleeps
14
Maryland
>
Annapolis House
#3025232
1 Review
Compare
Naval Stadium access at its BEST. Unique, Great for Celebration/City Tour Home
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Naval Stadium access at its BEST. Unique, Great for Celebration/City Tour Home
3
BR,
2
BA,
Sleeps
8
Maryland
>
Annapolis House
#249787
Compare
49 More choices from HomeAway International Websites
Charming Historic Home Just Steps From Main Street!
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$450
per night
Charming Historic Home Just Steps From Main Street!
Book it Now!
2 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Maryland
>
Annapolis House
#458610vb
(5)
Compare
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