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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 61 Cottages in Friendship with updated reviews, rates, and availability.

Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Eastern Shore Waterside Cottage Near St. Michaels
Terrace/patio

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
Exterior

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
Exterior

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
Property grounds

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

9.8 out of 10, Exceptional, (24)
"Perfect place for a family, centrally located to everything you need for a fun vacation."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Amazing views, short walks to great dining!
Iron/ironing board, travel crib, free WiFi, bed sheets

Amazing views, short walks to great dining!

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 to great dining!
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, (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
Fridge, microwave, stovetop, dishwasher

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (30)
"Our family was in town to attend the promotion in the air force of a nephew at Ft. McNair. Close to everything. Beautiful house prefect for us. Enjoyed walking the boardwalk. Would highly recommend this property. Excellent communication with the host. "
North Beach Cottage - Walk to Chesapeake Bay
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, (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!
Interior

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
Fridge, microwave, oven, stovetop

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!
Outdoor dining

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
Exterior

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

10.0 out of 10, Exceptional, (39)
"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "
Accessible, Screened-in porch, Water Access, 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, (43)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is SAR 600
SAR 1,177 total
includes taxes & fees
28 Apr - 29 Apr
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, (8)
"Perfect location for family visit at USNA! House was super clean and cozy with easy access to all downtown and academy events."
The price is SAR 1,501
SAR 2,524 total
includes taxes & fees
5 May - 6 May
Secluded Cozy Cottage in Historic Downtown
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

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.
Exterior

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
Exterior

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.
Terrace/patio

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 SAR 750
SAR 1,194 total
includes taxes & fees
14 May - 15 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher

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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Other property types in Friendship

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (211)
"Everything was just as advertised!! Very charming house in a perfect location. Wonderful gas fireplace in the living room, cute back patio, everything we needed and more! This house was absolutely spotless!! A to the cleaning people!! John was a wonderful host! Went out of his way to check on us and offer any assistance if we needed it. We "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (74)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Chesapeake Houseboat Getaway on Kent Island, Maryland
Smart TV, fireplace

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (24)
"Our weekend stay at Julia’s Arc was truly the perfect weekend!!! The location is perfect and the boat is so clean, cozy, beautifully decorated, and generously stocked. We felt so calm and happy during our whole stay. The top deck is a perfect spot to have a cup of coffee or watch the sunset. Plus, the host, Julia was so accommodating and sweet. We really hope to go back soon! "
Chesapeake Houseboat Getaway on Kent Island, Maryland
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.