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Annapolis Vacation Rentals

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402 rentals in Annapolis.
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Walk to Main Street from this newly-renovated Historic home!, vacation rental in Annapolis
Walk to Main Street from this newly-renovated Historic home!, vacation rental in Annapolis
Walk to Main Street from this newly-renovated Historic home!, vacation rental in Annapolis

Walk to Main Street from this newly-renovated Historic home!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
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Cozy place close to the city dock, vacation rental in Annapolis
Cozy place close to the city dock, vacation rental in Annapolis
Cozy place close to the city dock, vacation rental in Annapolis

Cozy place close to the city dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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
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Eastport Condo in Building with Rooftop Water Views of Spa Creek!, vacation rental in Annapolis
Eastport Condo in Building with Rooftop Water Views of Spa Creek!, vacation rental in Annapolis
Eastport Condo in Building with Rooftop Water Views of Spa Creek!, vacation rental in Annapolis

Eastport Condo in Building with Rooftop Water Views of Spa Creek!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Calico Cottage Guest House, vacation rental in Annapolis
Calico Cottage Guest House, vacation rental in Annapolis
Calico Cottage Guest House, vacation rental in Annapolis

Calico Cottage Guest House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Private Apartment - Minutes to USNA, vacation rental in Annapolis
Private Apartment - Minutes to USNA, vacation rental in Annapolis
Private Apartment - Minutes to USNA, vacation rental in Annapolis

Private Apartment - Minutes to USNA

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS, vacation rental in Annapolis
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS, vacation rental in Annapolis
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS, vacation rental in Annapolis

COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Welcome Aboard the Back of the Moon, vacation rental in Annapolis
Welcome Aboard the Back of the Moon, vacation rental in Annapolis
Welcome Aboard the Back of the Moon, vacation rental in Annapolis

Welcome Aboard the Back of the Moon

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Spacious and Comfortable Basement Apartment, vacation rental in Annapolis
Spacious and Comfortable Basement Apartment, vacation rental in Annapolis
Spacious and Comfortable Basement Apartment, vacation rental in Annapolis

Spacious and Comfortable Basement Apartment

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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A Serene Tiny Home Experience, vacation rental in Annapolis
A Serene Tiny Home Experience, vacation rental in Annapolis
A Serene Tiny Home Experience, vacation rental in Annapolis

A Serene Tiny Home Experience

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Cozy Downtown Annapolis Apartment, vacation rental in Annapolis
Cozy Downtown Annapolis Apartment, vacation rental in Annapolis
Cozy Downtown Annapolis Apartment, vacation rental in Annapolis

Cozy Downtown Annapolis Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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
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Downtown furnished apartment - walking distance to restaurants, vacation rental in Annapolis
Downtown furnished apartment - walking distance to restaurants, vacation rental in Annapolis
Downtown furnished apartment - walking distance to restaurants, vacation rental in Annapolis

Downtown furnished apartment - walking distance to restaurants

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Beautiful Condo by the Naval Academy, vacation rental in Annapolis
Beautiful Condo by the Naval Academy, vacation rental in Annapolis
Beautiful Condo by the Naval Academy, vacation rental in Annapolis

Beautiful Condo by the Naval Academy

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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WALK TO EASTPORT AND HISTORIC DOWNTOWN ANNAPOLIS - Quaint Cottage is the, vacation rental in Annapolis
WALK TO EASTPORT AND HISTORIC DOWNTOWN ANNAPOLIS - Quaint Cottage is the, vacation rental in Annapolis
WALK TO EASTPORT AND HISTORIC DOWNTOWN ANNAPOLIS - Quaint Cottage is the, vacation rental in Annapolis

WALK TO EASTPORT AND HISTORIC DOWNTOWN ANNAPOLIS - Quaint Cottage is the

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Eastport Hideaway - Perfect little guesthouse for 2, vacation rental in Annapolis
Eastport Hideaway - Perfect little guesthouse for 2, vacation rental in Annapolis
Eastport Hideaway - Perfect little guesthouse for 2, vacation rental in Annapolis

Eastport Hideaway - Perfect little guesthouse for 2

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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6 month minimum - Enjoy this wonderful condo in the heart of Eastport close to p, vacation rental in Annapolis
6 month minimum - Enjoy this wonderful condo in the heart of Eastport close to p, vacation rental in Annapolis
6 month minimum - Enjoy this wonderful condo in the heart of Eastport close to p, vacation rental in Annapolis

6 month minimum - Enjoy this wonderful condo in the heart of Eastport close to p

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Annapolis Garden Suite, vacation rental in Annapolis
Annapolis Garden Suite, vacation rental in Annapolis
Annapolis Garden Suite, vacation rental in Annapolis

Annapolis Garden Suite

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Annapolis Historic District rowhome w/ parking and rooftop deck, vacation rental in Annapolis
Annapolis Historic District rowhome w/ parking and rooftop deck, vacation rental in Annapolis
Annapolis Historic District rowhome w/ parking and rooftop deck, vacation rental in Annapolis

Annapolis Historic District rowhome w/ parking and rooftop deck

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., vacation rental in Annapolis
Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., vacation rental in Annapolis
Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., vacation rental in Annapolis

Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer...

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Eastport condo is located in a waterfront community with a community pool, vacation rental in Annapolis
Eastport condo is located in a waterfront community with a community pool, vacation rental in Annapolis
Eastport condo is located in a waterfront community with a community pool, vacation rental in Annapolis

Eastport condo is located in a waterfront community with a community pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis), vacation rental in Annapolis
New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis), vacation rental in Annapolis
New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis), vacation rental in Annapolis

New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Convenient Eastport condo with beautiful water views and community pool!, vacation rental in Annapolis
Convenient Eastport condo with beautiful water views and community pool!, vacation rental in Annapolis
Convenient Eastport condo with beautiful water views and community pool!, vacation rental in Annapolis

Convenient Eastport condo with beautiful water views and community pool!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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“Athens of America,” Annapolis Apartment Two A, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment Two A, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment Two A, vacation rental in Annapolis

“Athens of America,” Annapolis Apartment Two A

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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“Athens of America,” Annapolis Apartment Two B, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment Two B, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment Two B, vacation rental in Annapolis

“Athens of America,” Annapolis Apartment Two B

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Chill in Mellow Yellow with PARKING!, vacation rental in Annapolis
Chill in Mellow Yellow with PARKING!, vacation rental in Annapolis
Chill in Mellow Yellow with PARKING!, vacation rental in Annapolis

Chill in Mellow Yellow with PARKING!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Renovated Rowhome in the Heart of Downtown Annapolis Historic District!, vacation rental in Annapolis
Renovated Rowhome in the Heart of Downtown Annapolis Historic District!, vacation rental in Annapolis
Renovated Rowhome in the Heart of Downtown Annapolis Historic District!, vacation rental in Annapolis

Renovated Rowhome in the Heart of Downtown Annapolis Historic District!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Oasis of Annapolis Blue, vacation rental in Annapolis
Waterfront Oasis of Annapolis Blue, vacation rental in Annapolis
Waterfront Oasis of Annapolis Blue, vacation rental in Annapolis

Waterfront Oasis of Annapolis Blue

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, vacation rental in Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, vacation rental in Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, vacation rental in Annapolis

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Legislative Session Available, vacation rental in Annapolis
Legislative Session Available, vacation rental in Annapolis
Legislative Session Available, vacation rental in Annapolis

Legislative Session Available

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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This fabulous condo is picture perfect with its furnishings and appointments. En, vacation rental in Annapolis
This fabulous condo is picture perfect with its furnishings and appointments. En, vacation rental in Annapolis
This fabulous condo is picture perfect with its furnishings and appointments. En, vacation rental in Annapolis

This fabulous condo is picture perfect with its furnishings and appointments. En

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Bright Big Window Loft Heart of Eastport, vacation rental in Annapolis
Amazing Bright Big Window Loft Heart of Eastport, vacation rental in Annapolis
Amazing Bright Big Window Loft Heart of Eastport, vacation rental in Annapolis

Amazing Bright Big Window Loft Heart of Eastport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Spectacular Location: State Circle Apartment, vacation rental in Annapolis
Spectacular Location: State Circle Apartment, vacation rental in Annapolis
Spectacular Location: State Circle Apartment, vacation rental in Annapolis

Spectacular Location: State Circle Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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One-bedroom apartment with 3 fireplaces. Close to City Dock, vacation rental in Annapolis
One-bedroom apartment with 3 fireplaces. Close to City Dock, vacation rental in Annapolis
One-bedroom apartment with 3 fireplaces. Close to City Dock, vacation rental in Annapolis

One-bedroom apartment with 3 fireplaces. Close to City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Private Annapolis Guest Apartment! Walkable to downtown! Location!, vacation rental in Annapolis
Private Annapolis Guest Apartment! Walkable to downtown! Location!, vacation rental in Annapolis
Private Annapolis Guest Apartment! Walkable to downtown! Location!, vacation rental in Annapolis

Private Annapolis Guest Apartment! Walkable to downtown! Location!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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You will surely appreciate the convenience of off-street parking and the, vacation rental in Annapolis
You will surely appreciate the convenience of off-street parking and the, vacation rental in Annapolis
You will surely appreciate the convenience of off-street parking and the, vacation rental in Annapolis

You will surely appreciate the convenience of off-street parking and the

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport, vacation rental in Annapolis
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport, vacation rental in Annapolis
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport, vacation rental in Annapolis

Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Downtown Getaway- Across from US Naval Academy, vacation rental in Annapolis
Spacious Downtown Getaway- Across from US Naval Academy, vacation rental in Annapolis
Spacious Downtown Getaway- Across from US Naval Academy, vacation rental in Annapolis

Spacious Downtown Getaway- Across from US Naval Academy

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Waterfront Cottage with Views, Dock & Boat, vacation rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, vacation rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, vacation rental in Annapolis

Charming Waterfront Cottage with Views, Dock & Boat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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“Athens of America,” Annapolis Apartment One B, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment One B, vacation rental in Annapolis
“Athens of America,” Annapolis Apartment One B, vacation rental in Annapolis

“Athens of America,” Annapolis Apartment One B

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis
Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis
Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis

Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Recently remodeled 1 bedroom and 1 bathroom condo with water views of Spa Creek., vacation rental in Annapolis
Recently remodeled 1 bedroom and 1 bathroom condo with water views of Spa Creek., vacation rental in Annapolis
Recently remodeled 1 bedroom and 1 bathroom condo with water views of Spa Creek., vacation rental in Annapolis

Recently remodeled 1 bedroom and 1 bathroom condo with water views of Spa Creek.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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After a long day, park and take a walk to a favorite Eastport pub or restaurant, vacation rental in Annapolis
After a long day, park and take a walk to a favorite Eastport pub or restaurant, vacation rental in Annapolis
After a long day, park and take a walk to a favorite Eastport pub or restaurant, vacation rental in Annapolis

After a long day, park and take a walk to a favorite Eastport pub or restaurant

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful new condo in ideal West Annapolis location. This condo has vaulted, vacation rental in Annapolis
Beautiful new condo in ideal West Annapolis location. This condo has vaulted, vacation rental in Annapolis
Beautiful new condo in ideal West Annapolis location. This condo has vaulted, vacation rental in Annapolis

Beautiful new condo in ideal West Annapolis location. This condo has vaulted

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious 2nd Floor Apartment, with its own entrance and off-street parking., vacation rental in Annapolis
Spacious 2nd Floor Apartment, with its own entrance and off-street parking., vacation rental in Annapolis
Spacious 2nd Floor Apartment, with its own entrance and off-street parking., vacation rental in Annapolis

Spacious 2nd Floor Apartment, with its own entrance and off-street parking.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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Quaint, light-filed haven in heart of downtown Annapolis, vacation rental in Annapolis
Quaint, light-filed haven in heart of downtown Annapolis, vacation rental in Annapolis
Quaint, light-filed haven in heart of downtown Annapolis, vacation rental in Annapolis

Quaint, light-filed haven in heart of downtown Annapolis

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis, vacation rental in Annapolis
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis, vacation rental in Annapolis
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis, vacation rental in Annapolis

Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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