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
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 House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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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
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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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 House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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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 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 House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
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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 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 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 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 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 House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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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 House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Perfect historic home + Peloton, walk to downtown Annapolis
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer...
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Excellent Location, Super Clean, Super Spacious !!
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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Waterfront Chesapeake Cottage in Oyster Bay - Dock
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Beautifully furnished home close to Navy Stadium with Parking!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Large Luxury Apartment In Downtown Annapolis
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Charming Annapolis WaterVIEW Home
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps, Pet friendly
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Warm and welcoming Eastport home. Gracious sophistication in an ideal location.
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Beautiful family-friendly 4-Bdr home in Murray Hill
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, Pet friendly
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Parking & Pet Friendly USNA-themed Annapolis home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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ACROSS FROM STADIUM - walk to downtown Annapolis.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Little Magothy Riverfront Home With Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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All-stop. Rental Midships.
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Relaxing Bay Ridge Lagoon
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Parking and Pet Friendly Annapolis-themed home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Less than a block from Main Street - Heart Of Historic District!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Pet Friendly 2nd Floor Lofted apartment in Eastport
Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Pet friendly
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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
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NEW! Waterfront Annapolis Getaway w / Fishing Pier!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Beach Neighborhood Minutes From Naval Academy
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Cool 1870's Historic District Home with modern amenities
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Eastport Peninsula Charm
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Get Away On The Bay!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Everything's New - Annapolis Treasure
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Annapolis Garden Suite
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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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
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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 House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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The Heart of Historic Cool in Annapolis
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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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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