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Pet Friendly Holiday Rentals in Annapolis

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80 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, Pet friendly
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Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis

Charming historic home just steps from Main Street!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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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, Pet friendly
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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, Pet friendly
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, Pet friendly
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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, Pet friendly
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 7
Match: Sleeps, Pet friendly
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Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, holiday rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, holiday rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, holiday rental in Annapolis

Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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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, Pet friendly
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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, Pet friendly
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Historic District Renovated Home Available for 2023 Legislative Session, holiday rental in Annapolis
Historic District Renovated Home Available for 2023 Legislative Session, holiday rental in Annapolis
Historic District Renovated Home Available for 2023 Legislative Session, holiday rental in Annapolis

Historic District Renovated Home Available for 2023 Legislative Session

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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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, Pet friendly
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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, Pet friendly
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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, Pet friendly
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Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis

Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Historic District"Crab Cakes and Football", holiday rental in Annapolis
Historic District"Crab Cakes and Football", holiday rental in Annapolis
Historic District"Crab Cakes and Football", holiday rental in Annapolis

Historic District"Crab Cakes and Football"

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis

Nautical Feel to This Beautiful Eastport Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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, Pet friendly
More info
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Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., holiday rental in Annapolis
Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., holiday rental in Annapolis
Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer..., holiday rental in Annapolis

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
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Excellent Location, Super Clean, Super Spacious !!, holiday rental in Annapolis
Excellent Location, Super Clean, Super Spacious !!, holiday rental in Annapolis
Excellent Location, Super Clean, Super Spacious !!, holiday rental in Annapolis

Excellent Location, Super Clean, Super Spacious !!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
More info
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Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis

Waterfront Chesapeake Cottage in Oyster Bay - Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Beautifully furnished home close to Navy Stadium with Parking!, holiday rental in Annapolis
Beautifully furnished home close to Navy Stadium with Parking!, holiday rental in Annapolis
Beautifully furnished home close to Navy Stadium with Parking!, holiday rental in Annapolis

Beautifully furnished home close to Navy Stadium with Parking!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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Large Luxury Apartment In Downtown Annapolis, holiday rental in Annapolis
Large Luxury Apartment In Downtown Annapolis, holiday rental in Annapolis
Large Luxury Apartment In Downtown Annapolis, holiday rental in Annapolis

Large Luxury Apartment In Downtown Annapolis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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 13
Match: Sleeps, Pet friendly
More info
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Warm and welcoming Eastport home. Gracious sophistication in an ideal location., holiday rental in Annapolis
Warm and welcoming Eastport home. Gracious sophistication in an ideal location., holiday rental in Annapolis
Warm and welcoming Eastport home. Gracious sophistication in an ideal location., holiday rental in Annapolis

Warm and welcoming Eastport home. Gracious sophistication in an ideal location.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Beautiful family-friendly 4-Bdr home in Murray Hill, holiday rental in Annapolis
Beautiful family-friendly 4-Bdr home in Murray Hill, holiday rental in Annapolis
Beautiful family-friendly 4-Bdr home in Murray Hill, holiday rental in Annapolis

Beautiful family-friendly 4-Bdr home in Murray Hill

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, Pet friendly
More info
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Parking & Pet Friendly USNA-themed Annapolis home, holiday rental in Annapolis
Parking & Pet Friendly USNA-themed Annapolis home, holiday rental in Annapolis
Parking & Pet Friendly USNA-themed Annapolis home, holiday rental in Annapolis

Parking & Pet Friendly USNA-themed Annapolis home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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 10
Match: Sleeps, Pet friendly
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, Pet friendly
More info
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All-stop.  Rental Midships., holiday rental in Annapolis
All-stop.  Rental Midships., holiday rental in Annapolis
All-stop.  Rental Midships., holiday rental in Annapolis

All-stop. Rental Midships.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
More info
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Relaxing Bay Ridge Lagoon, holiday rental in Annapolis
Relaxing Bay Ridge Lagoon, holiday rental in Annapolis
Relaxing Bay Ridge Lagoon, holiday rental in Annapolis

Relaxing Bay Ridge Lagoon

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere., holiday rental in Annapolis
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere., holiday rental in Annapolis
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere., holiday rental in Annapolis

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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Parking and Pet Friendly Annapolis-themed home, holiday rental in Annapolis
Parking and Pet Friendly Annapolis-themed home, holiday rental in Annapolis
Parking and Pet Friendly Annapolis-themed home, holiday rental in Annapolis

Parking and Pet Friendly Annapolis-themed home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
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Less than a block from Main Street - Heart Of Historic District!, holiday rental in Annapolis
Less than a block from Main Street - Heart Of Historic District!, holiday rental in Annapolis
Less than a block from Main Street - Heart Of Historic District!, holiday rental in Annapolis

Less than a block from Main Street - Heart Of Historic District!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
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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, Pet friendly
More info
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The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium, holiday rental in Annapolis
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium, holiday rental in Annapolis
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium, holiday rental in Annapolis

The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
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, Pet friendly
More info
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Beach Neighborhood Minutes From Naval Academy, holiday rental in Annapolis
Beach Neighborhood Minutes From Naval Academy, holiday rental in Annapolis
Beach Neighborhood Minutes From Naval Academy, holiday rental in Annapolis

Beach Neighborhood Minutes From Naval Academy

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Cool 1870's Historic District Home with modern amenities, holiday rental in Annapolis
Cool 1870's Historic District Home with modern amenities, holiday rental in Annapolis
Cool 1870's Historic District Home with modern amenities, holiday rental in Annapolis

Cool 1870's Historic District Home with modern amenities

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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Eastport Peninsula Charm, holiday rental in Annapolis
Eastport Peninsula Charm, holiday rental in Annapolis
Eastport Peninsula Charm, holiday rental in Annapolis

Eastport Peninsula Charm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Get Away On The Bay!, holiday rental in Annapolis
Get Away On The Bay!, holiday rental in Annapolis
Get Away On The Bay!, holiday rental in Annapolis

Get Away On The Bay!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis, holiday rental in Annapolis
Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis, holiday rental in Annapolis
Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis, holiday rental in Annapolis

Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
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Everything's New - Annapolis Treasure, holiday rental in Annapolis
Everything's New - Annapolis Treasure, holiday rental in Annapolis
Everything's New - Annapolis Treasure, holiday rental in Annapolis

Everything's New - Annapolis Treasure

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Annapolis Garden Suite, holiday rental in Annapolis
Annapolis Garden Suite, holiday rental in Annapolis
Annapolis Garden Suite, holiday rental in Annapolis

Annapolis Garden Suite

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
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Private Pet-friendly Coastal Suite with water views just minutes to Annapolis, holiday rental in Annapolis
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis, holiday rental in Annapolis
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis, holiday rental in Annapolis

Private Pet-friendly Coastal Suite with water views just minutes to Annapolis

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
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Admiral's Retreat - Pet friendly, 1 mile to Navy Stadium with Parking!, holiday rental in Annapolis
Admiral's Retreat - Pet friendly, 1 mile to Navy Stadium with Parking!, holiday rental in Annapolis
Admiral's Retreat - Pet friendly, 1 mile to Navy Stadium with Parking!, holiday rental in Annapolis

Admiral's Retreat - Pet friendly, 1 mile to Navy Stadium with Parking!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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Eastport Gem - Popular house Walk to Downtown & USNA, holiday rental in Annapolis
Eastport Gem - Popular house Walk to Downtown & USNA, holiday rental in Annapolis
Eastport Gem - Popular house Walk to Downtown & USNA, holiday rental in Annapolis

Eastport Gem - Popular house Walk to Downtown & USNA

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Adorable home steps from Navy Stadium!, holiday rental in Annapolis
Adorable home steps from Navy Stadium!, holiday rental in Annapolis
Adorable home steps from Navy Stadium!, holiday rental in Annapolis

Adorable home steps from Navy Stadium!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
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The Heart of Historic Cool in Annapolis, holiday rental in Annapolis
The Heart of Historic Cool in Annapolis, holiday rental in Annapolis
The Heart of Historic Cool in Annapolis, holiday rental in Annapolis

The Heart of Historic Cool in Annapolis

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
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Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, holiday rental in Annapolis

Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
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Payment Protection

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