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Compare 64 Cottages in Friendship with updated reviews, rates, and availability.

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (19)
"We were traveling for a wedding at a near by venue. Plenty of room for our needs. We enjoyed visiting the small beach across the stress for coffee in the mornings! "
Cozy Cottage with access to and partially obstructed views of the bay.

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

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

10.0 out of 10, Exceptional, (207)
"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

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

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

10.0 out of 10, Exceptional, (24)
"We booked this rental for a few nights getaway for my family which included kids and "seasoned" adults. The view of the river was our favorite. The hot tub was a kid favorite. A pet friendly house was also a plus. The house is cozy, has charm and modern upgrades. 2 bathrooms is a plus. The spiral staircase was a challenge for the older adults but the outdoor stairs were more manageable for them. The house is clean, nicely decorated and had everything we needed. The owners were very...
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

10.0 out of 10, Exceptional, (80)
"We had a wonderful stay! Very cozy with beautiful views. Our host was very helpful and made sure our stay was great! Will definitely be back! "
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (32)
"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

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (3)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

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

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

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

10.0 out of 10, Exceptional, (40)
"We loved our stay. The house was spotless; Mark and Karen have provided everything one could possibly need, and they were super responsive. We enjoyed the porch, sauna, and fire pit; and our dog enjoyed the fully fenced backyard, nearby hikes, and dog-friendly local restaurants. Highly recommend!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (43)
"Quiet and tranquil. Nicely decorated and will definitely stay here again when we return to the area. "
The price is AED 588
AED 1,141 total
includes taxes & fees
6 May - 7 May
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"We had a very lovely stay . This is an excellent location . "
The price is AED 1,469
AED 2,471 total
includes taxes & fees
5 May - 6 May
Secluded Cozy Cottage in Historic Downtown

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more. "
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

9.8 out of 10, Exceptional, (34)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (157)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.0 out of 10, Wonderful, (2)
"The owner was very nice "
The price is AED 735
AED 1,189 total
includes taxes & fees
1 May - 2 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Adorable cottage with updated amenities. A great retreat for friends or a family!! "
Updated North Beach Cottage: Pet Friendly!
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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Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"We stayed at the host property for a long weekend in town for a family baby shower nearby. We were totally impressed with the cleanliness of the location, spacious accommodations and responsiveness of the host. There is a weekend farmers market and we wound up getting fresh produce to cook and some great food and desserts to eat. Parking was a breeze and the nearby park was wonderful for our daily walks. Highly recommended! 10 out of 10!!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (214)
"Great location near the Naval Academy, Main Street, Paca House, St. John's...loved walking the streets every evening with our dog. Helpful restaurant trips from John, convenient parking spot, everything was just right! Thank you!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes
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.