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Holiday Rentals in Annapolis

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409 rentals in Annapolis.
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis

The Yellow Cottage on Harness Creek

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis

Space & Relaxation you Crave ! With plenty of Parking!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis

La Maison - Stunning waterfront views with pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis

Welcome Aboard the Kathleen Marie!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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We Get Repeat Renters!!, holiday rental in Annapolis
We Get Repeat Renters!!, holiday rental in Annapolis
We Get Repeat Renters!!, holiday rental in Annapolis

We Get Repeat Renters!!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Large Contemporary in Wooded Privacy, holiday rental in Annapolis
Large Contemporary in Wooded Privacy, holiday rental in Annapolis
Large Contemporary in Wooded Privacy, holiday rental in Annapolis

Large Contemporary in Wooded Privacy

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Water Views - Close to Downtown Annapolis, holiday rental in Annapolis
Water Views - Close to Downtown Annapolis, holiday rental in Annapolis
Water Views - Close to Downtown Annapolis, holiday rental in Annapolis

Water Views - Close to Downtown Annapolis

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis

Charming Annapolis Victorian

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Historic District Renovated Home, holiday rental in Annapolis
Historic District Renovated Home, holiday rental in Annapolis
Historic District Renovated Home, holiday rental in Annapolis

Historic District Renovated Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis
Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis
Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis

Annapolis Condominium in the heart of the historic center

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis

Tastefully decorated Eastport Annapolis house with water views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis

The Cottage on Spa Creek

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis

Historic Annapolis Home And Garden

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quiet Relaxing Waterfront Suisse Chalet - Valentine&#39;s Day weekend Special!, holiday rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Valentine&#39;s Day weekend Special!, holiday rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Valentine&#39;s Day weekend Special!, holiday rental in Annapolis

Quiet Relaxing Waterfront Suisse Chalet - Valentine&#39;s Day weekend Special!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis

Heart of Historic District!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis

Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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a charming 2 bedrooms home in historic Annapolis with parking!!, holiday rental in Annapolis
a charming 2 bedrooms home in historic Annapolis with parking!!, holiday rental in Annapolis
a charming 2 bedrooms home in historic Annapolis with parking!!, holiday rental in Annapolis

a charming 2 bedrooms home in historic Annapolis with parking!!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, holiday rental in Annapolis
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, holiday rental in Annapolis
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, holiday rental in Annapolis

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Lovely Family Home Just Minutes From Annapolis, holiday rental in Annapolis
Lovely Family Home Just Minutes From Annapolis, holiday rental in Annapolis
Lovely Family Home Just Minutes From Annapolis, holiday rental in Annapolis

Lovely Family Home Just Minutes From Annapolis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis

PERFECT LOCATION in the heart of history

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
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Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis

Walk to Naval Academy + City Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
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Perfect historic home + Peloton, walk to downtown Annapolis, holiday rental in Annapolis
Perfect historic home + Peloton, walk to downtown Annapolis, holiday rental in Annapolis
Perfect historic home + Peloton, walk to downtown Annapolis, holiday rental in Annapolis

Perfect historic home + Peloton, walk to downtown Annapolis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis

Two Blocks to Town, Underground Parking Garage

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, holiday rental in Annapolis
Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, holiday rental in Annapolis
Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis, holiday rental in Annapolis

Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis

Beautiful Historic Home With Great Location!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis

Best Location. Best Price. Across from Gate One & Steps from the Waterfront

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis

Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis, holiday rental in Annapolis
Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis, holiday rental in Annapolis
Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis, holiday rental in Annapolis

Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Now Available Commissioning Week 2023! (May 19th to May 27th), holiday rental in Annapolis
Now Available Commissioning Week 2023! (May 19th to May 27th), holiday rental in Annapolis
Now Available Commissioning Week 2023! (May 19th to May 27th), holiday rental in Annapolis

Now Available Commissioning Week 2023! (May 19th to May 27th)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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*Perfect spot for a Weekend Getaway or longer term rental*, holiday rental in Annapolis
*Perfect spot for a Weekend Getaway or longer term rental*, holiday rental in Annapolis
*Perfect spot for a Weekend Getaway or longer term rental*, holiday rental in Annapolis

*Perfect spot for a Weekend Getaway or longer term rental*

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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Waterfront Oasis of Annapolis Blue, holiday rental in Annapolis
Waterfront Oasis of Annapolis Blue, holiday rental in Annapolis
Waterfront Oasis of Annapolis Blue, holiday rental in Annapolis

Waterfront Oasis of Annapolis Blue

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Little Magothy Riverfront Home With Pool, holiday rental in Annapolis
Little Magothy Riverfront Home With Pool, holiday rental in Annapolis
Little Magothy Riverfront Home With Pool, holiday rental in Annapolis

Little Magothy Riverfront Home With Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-50 of 409
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