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Holiday Rentals in Annapolis

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
490 rentals in Annapolis.
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis

Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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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
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Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis
Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis
Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis

Waterfront Oasis of Annapolis FIRSTIE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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Cozy Downtown Annapolis Apartment, holiday rental in Annapolis
Cozy Downtown Annapolis Apartment, holiday rental in Annapolis
Cozy Downtown Annapolis Apartment, holiday rental in Annapolis

Cozy Downtown Annapolis Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Payment Protection
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 3
Match: Sleeps
More info
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Cozy place close to the city dock, holiday rental in Annapolis
Cozy place close to the city dock, holiday rental in Annapolis
Cozy place close to the city dock, holiday rental in Annapolis

Cozy place close to the city dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis

Charming Waterfront Cottage with Views, Dock & Boat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis

3 Story Stunner in Murray Hill <1 mile from USNA!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis
Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis
Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis

Historic District Charm with two mid-size or smaller parking spots!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy 1st Floor King George one bedroom apartment right across from USNA, holiday rental in Annapolis
Cozy 1st Floor King George one bedroom apartment right across from USNA, holiday rental in Annapolis
Cozy 1st Floor King George one bedroom apartment right across from USNA, holiday 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
More info
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ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis

ACROSS FROM STADIUM - walk to downtown Annapolis.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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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 3
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
0 bathrooms
Sleeps 2
Match: Sleeps
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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 8
Match: Sleeps
More info
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Charming Annapolis WaterVIEW Home, holiday rental in Annapolis
Charming Annapolis WaterVIEW Home, holiday rental in Annapolis
Charming Annapolis WaterVIEW Home, holiday rental in Annapolis

Charming Annapolis WaterVIEW Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Cozy suite Located in Presidents Hill, holiday rental in Annapolis
Cozy suite Located in Presidents Hill, holiday rental in Annapolis
Cozy suite Located in Presidents Hill, holiday rental in Annapolis

Cozy suite Located in Presidents Hill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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
2 bedrooms
2 bathrooms
Sleeps 5
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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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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Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis
Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis
Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis

Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis
Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis
Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis

Happy days on the Bay at dog-friendly beachfront home on the Chesapeake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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 2
Match: Sleeps
More info
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Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, holiday rental in Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, holiday rental in Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with  private garage  Annapolis, holiday rental in Annapolis

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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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Bay View Studio Apartment, holiday rental in Annapolis
Bay View Studio Apartment, holiday rental in Annapolis
Bay View Studio Apartment, holiday rental in Annapolis

Bay View Studio Apartment

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

Freshly renovated 3-story home 1 block from USNA!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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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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Your Annapolis adventure starts here!!, holiday rental in Annapolis
Your Annapolis adventure starts here!!, holiday rental in Annapolis
Your Annapolis adventure starts here!!, holiday rental in Annapolis

Your Annapolis adventure starts here!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, holiday rental in Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, holiday rental in Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, holiday rental in Annapolis

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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 3
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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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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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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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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'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis
'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis
'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis

'Newer Cottage Incredibly and Comfortably Furnished.'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis
Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis
Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great location, free parking, holiday rental in Annapolis
Great location, free parking, holiday rental in Annapolis
Great location, free parking, holiday rental in Annapolis

Great location, free parking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
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Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis

Downtown Annapolis Townhome ! Beautiful!!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Condo Amazing Views with Resort Amenities, holiday rental in Annapolis
Waterfront Condo Amazing Views with Resort Amenities, holiday rental in Annapolis
Waterfront Condo Amazing Views with Resort Amenities, holiday rental in Annapolis

Waterfront Condo Amazing Views with Resort Amenities

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Payment Protection
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis

New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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Pet Friendly 2nd Floor Lofted apartment in Eastport, holiday rental in Annapolis
Pet Friendly 2nd Floor Lofted apartment in Eastport, holiday rental in Annapolis
Pet Friendly 2nd Floor Lofted apartment in Eastport, holiday rental in Annapolis

Pet Friendly 2nd Floor Lofted apartment in Eastport

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Chic Condo w/ Balcony in the Heart of Annapolis!, holiday rental in Annapolis
Chic Condo w/ Balcony in the Heart of Annapolis!, holiday rental in Annapolis
Chic Condo w/ Balcony in the Heart of Annapolis!, holiday rental in Annapolis

Chic Condo w/ Balcony in the Heart of Annapolis!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis
NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis
NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis

NEW! Waterfront Annapolis Getaway w / Fishing Pier!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 490
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