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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

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

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

9.2 out of 10, Wonderful, (20)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (33)
"The place was wonderful, clean and well stocked. It was a great place to stay - kudos to the hosts for an inviting atmosphere."
North Beach Cottage - Walk to Chesapeake Bay
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (44)
"We live in Washington DC and wanted to get out of town for inauguration weekend, so we stayed at this home. This was our second time staying here and we will definitely be going back. The home is perfect. Super cozy, super clean, and very quiet. The hosts are the nicest people ever, which makes staying there even more pleasurable. "
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

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

10.0 out of 10, Exceptional, (44)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is AED 588
AED 1,129 total
includes taxes & fees
8 Jun - 9 Jun
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is AED 1,488
AED 2,512 total
includes taxes & fees
2 Jun - 3 Jun
Secluded Cozy Cottage in Historic Downtown
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

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

10.0 out of 10, Exceptional, (27)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

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

10.0 out of 10, Exceptional, (208)
"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
Perfect location for USNA Commissioning Week
View from property

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (82)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Perfect location for USNA Commissioning Week
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Marina

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

9.8 out of 10, Exceptional, (36)
"We had a great stay in this quiet beautiful house. Annapolis was close by and a fun time."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (10)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

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

9.8 out of 10, Exceptional, (28)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (91)
"Great property right outside of north beach"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Really enjoyed our stay, pool was nice and had plenty of amenities. We will definitely be coming back for another stay."
Eastern Shore Waterside Cottage Near St. Michaels
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

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

10.0 out of 10, Exceptional, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Miscellaneous

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 1,169 total
includes taxes & fees
9 Jun - 10 Jun
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books

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
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (15)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
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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