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Browse Select Parole Cottages

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (293)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (49)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (90)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (16)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (83)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (1)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!

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

9.8 out of 10, Exceptional, (29)
"Tranquil cottage by the river to relax and reconnect for couples. Quick drive to Annapolis mall and downtown. Lots of outdoor seating to enjoy. Hosts were very responsive to our questions and request for bikes. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (28)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (211)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (113)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (8)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

New Home w Luxe King Suite, Porch Vibes & Parking

New Home w Luxe King Suite, Porch Vibes & Parking

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Vacation Rental w/ Yard in Washington, DC, Area

3.0 star property
Vacation Rental w/ Yard in Washington, DC, Area

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Convenient enough and out of the way enough to enjoy Annapolis for the weekend. Well appointed and comfortable for the four of us. "
Enchanting West River Retreat
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.
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