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Top Cottages in Annapolis

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis MD

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This cottage features a garden, laundry facilities, and barbecue grills.

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA

Annapolis MD

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A hot tub is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Your Annapolis Waterfront retreat for a weekend getaway.

Annapolis MD

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This cottage features a garden, a picnic area, and barbecue grills.

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$657 nightly

$749 total

May 11 - May 12

Total with taxes and fees

This cottage features a terrace, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

The Yellow Cottage on Harness Creek

Annapolis MD

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This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

1 Block to Usna Stadium: Modern Annapolis Home!

Annapolis MD

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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Kitchen

Washer

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

Annapolis MD

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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Waterfront Annapolis Cottage: Fire Pit & Pier

Annapolis MD

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This cottage includes free WiFi in public areas and barbecue grills.

Walk to Everything - Historic Art’s District

Annapolis MD

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This cottage features laundry facilities.

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis MD

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A hot tub is featured at this cottage, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Annapolis MD

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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Walk to everything! Downtown Historic Annapolis “Arts District”

Annapolis MD

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Stay at this cottage in Annapolis. Enjoy air conditioning. Popular attractions Chesapeake Bay Bridge and Annapolis Civil Rights Plaque are located nearby.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.