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Annapolis Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
428 rentals in Annapolis.
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Amazing views, short walks to great dining!, vacation rental in Annapolis
Amazing views, short walks to great dining!, vacation rental in Annapolis
Amazing views, short walks to great dining!, vacation rental in Annapolis

Amazing views, short walks to great dining!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fantastic Location In DTA with its own Parking!, vacation rental in Annapolis
Fantastic Location In DTA with its own Parking!, vacation rental in Annapolis
Fantastic Location In DTA with its own Parking!, vacation rental in Annapolis

Fantastic Location In DTA with its own Parking!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy 1st Floor King George one bedroom apartment right across from USNA, vacation rental in Annapolis
Cozy 1st Floor King George one bedroom apartment right across from USNA, vacation rental in Annapolis
Cozy 1st Floor King George one bedroom apartment right across from USNA, vacation rental in Annapolis

Cozy 1st Floor King George one bedroom apartment right across from USNA

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy suite Located in Presidents Hill, vacation rental in Annapolis
Cozy suite Located in Presidents Hill, vacation rental in Annapolis
Cozy suite Located in Presidents Hill, vacation rental in Annapolis

Cozy suite Located in Presidents Hill

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach, vacation rental in Annapolis
Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach, vacation rental in Annapolis
Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach, vacation rental in Annapolis

Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, vacation rental in Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, vacation rental in Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, vacation rental in Annapolis

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bay View Studio Apartment, vacation rental in Annapolis
Bay View Studio Apartment, vacation rental in Annapolis
Bay View Studio Apartment, vacation rental in Annapolis

Bay View Studio Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Freshly renovated 3-story home 1 block from USNA!, vacation rental in Annapolis
Freshly renovated 3-story home 1 block from USNA!, vacation rental in Annapolis
Freshly renovated 3-story home 1 block from USNA!, vacation rental in Annapolis

Freshly renovated 3-story home 1 block from USNA!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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La Maison - Stunning waterfront views with pool, vacation rental in Annapolis
La Maison - Stunning waterfront views with pool, vacation rental in Annapolis
La Maison - Stunning waterfront views with pool, vacation rental in Annapolis

La Maison - Stunning waterfront views with pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis

Downtown Annapolis Townhome ! Beautiful!!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis

Location Location Location!!!50 Steps from Main Street and all of the action

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis

Welcome Aboard the Kathleen Marie!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chic Condo w/ Balcony in the Heart of Annapolis!, vacation rental in Annapolis
Chic Condo w/ Balcony in the Heart of Annapolis!, vacation rental in Annapolis
Chic Condo w/ Balcony in the Heart of Annapolis!, vacation rental in Annapolis

Chic Condo w/ Balcony in the Heart of Annapolis!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis
Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis
Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Carriage House close to USNA, walk to stadium, free parking,  pets+kids, vacation rental in Annapolis
Gorgeous Carriage House close to USNA, walk to stadium, free parking,  pets+kids, vacation rental in Annapolis
Gorgeous Carriage House close to USNA, walk to stadium, free parking,  pets+kids, vacation rental in Annapolis

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Nautical Feel to This Beautiful Eastport Home, vacation rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, vacation rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, vacation rental in Annapolis

Nautical Feel to This Beautiful Eastport Home

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, vacation rental in Annapolis
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, vacation rental in Annapolis
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, vacation rental in Annapolis

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard, vacation rental in Annapolis
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard, vacation rental in Annapolis
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard, vacation rental in Annapolis

Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis
Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis
Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis

Private Waterfront Woods | Dock, Kayaks, Views

Rental Home
5 bedrooms
4 bathrooms
Sleeps 19
Match: Sleeps
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Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis

Historic Annapolis Home 1.5 blocks from center of town.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, vacation rental in Annapolis
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, vacation rental in Annapolis
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, vacation rental in Annapolis

Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis
Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis
Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis

Charming Historic Townhouse Steps From USNA

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis

Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock

Rental Home
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!, vacation rental in Annapolis
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!, vacation rental in Annapolis
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!, vacation rental in Annapolis

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, vacation rental in Annapolis
Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, vacation rental in Annapolis
Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, vacation rental in Annapolis

Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,, vacation rental in Annapolis
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,, vacation rental in Annapolis
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,, vacation rental in Annapolis

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Coastal Cabins., vacation rental in Annapolis
Coastal Cabins., vacation rental in Annapolis
Coastal Cabins., vacation rental in Annapolis

Coastal Cabins.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ideal Eastport/ Annapolis Location, vacation rental in Annapolis
Ideal Eastport/ Annapolis Location, vacation rental in Annapolis
Ideal Eastport/ Annapolis Location, vacation rental in Annapolis

Ideal Eastport/ Annapolis Location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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History & Charm steps from Main Street and City Dock, vacation rental in Annapolis
History & Charm steps from Main Street and City Dock, vacation rental in Annapolis
History & Charm steps from Main Street and City Dock, vacation rental in Annapolis

History & Charm steps from Main Street and City Dock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Adorable home steps from Navy Stadium!, vacation rental in Annapolis
Adorable home steps from Navy Stadium!, vacation rental in Annapolis
Adorable home steps from Navy Stadium!, vacation rental in Annapolis

Adorable home steps from Navy Stadium!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tastefully decorated fully-equipped Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated fully-equipped Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated fully-equipped Eastport Annapolis house with water views, vacation rental in Annapolis

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 4BR 2BA w/ outdoor patio! 5 min walk to Navy Stadium and DT, vacation rental in Annapolis
Charming 4BR 2BA w/ outdoor patio! 5 min walk to Navy Stadium and DT, vacation rental in Annapolis
Charming 4BR 2BA w/ outdoor patio! 5 min walk to Navy Stadium and DT, vacation rental in Annapolis

Charming 4BR 2BA w/ outdoor patio! 5 min walk to Navy Stadium and DT

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Recently Renovated Annapolis Home - Conveniently Located, vacation rental in Annapolis
Recently Renovated Annapolis Home - Conveniently Located, vacation rental in Annapolis
Recently Renovated Annapolis Home - Conveniently Located, vacation rental in Annapolis

Recently Renovated Annapolis Home - Conveniently Located

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace, vacation rental in Annapolis
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace, vacation rental in Annapolis
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace, vacation rental in Annapolis

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Anchor's Away in the Heart of Eastport!, vacation rental in Annapolis
Anchor's Away in the Heart of Eastport!, vacation rental in Annapolis
Anchor's Away in the Heart of Eastport!, vacation rental in Annapolis

Anchor's Away in the Heart of Eastport!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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NEW lovely studio apartment with onsite parking!, vacation rental in Annapolis
NEW lovely studio apartment with onsite parking!, vacation rental in Annapolis
NEW lovely studio apartment with onsite parking!, vacation rental in Annapolis

NEW lovely studio apartment with onsite parking!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!, vacation rental in Annapolis
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!, vacation rental in Annapolis
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!, vacation rental in Annapolis

Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded Cozy Cottage in Historic Downtown, vacation rental in Annapolis
Secluded Cozy Cottage in Historic Downtown, vacation rental in Annapolis
Secluded Cozy Cottage in Historic Downtown, vacation rental in Annapolis

Secluded Cozy Cottage in Historic Downtown

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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2003 Craftsman; Heart of Eastport!, vacation rental in Annapolis
2003 Craftsman; Heart of Eastport!, vacation rental in Annapolis
2003 Craftsman; Heart of Eastport!, vacation rental in Annapolis

2003 Craftsman; Heart of Eastport!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
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Heart of Eastport 4 bedroom Modern Craftsman!, vacation rental in Annapolis
Heart of Eastport 4 bedroom Modern Craftsman!, vacation rental in Annapolis
Heart of Eastport 4 bedroom Modern Craftsman!, vacation rental in Annapolis

Heart of Eastport 4 bedroom Modern Craftsman!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Charming Downtown 3rd Floor 1 Bedroom Apt, vacation rental in Annapolis
Charming Downtown 3rd Floor 1 Bedroom Apt, vacation rental in Annapolis
Charming Downtown 3rd Floor 1 Bedroom Apt, vacation rental in Annapolis

Charming Downtown 3rd Floor 1 Bedroom Apt

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Annapolis Tree House Apartment- luxury shower, separate space, vacation rental in Annapolis
Annapolis Tree House Apartment- luxury shower, separate space, vacation rental in Annapolis
Annapolis Tree House Apartment- luxury shower, separate space, vacation rental in Annapolis

Annapolis Tree House Apartment- luxury shower, separate space

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Showing results 1-50 of 428
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