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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Sunderland

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

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

10.0 out of 10, Exceptional, (48)
"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
Cottage Located on the Patuxent River!
Sun loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"A gorgeous property perfect for a quiet getaway from the city noise. The cottage is very charming, and perfect for two people. Very clean, accommodating, private and peaceful. The private beach is beyond charming and the local spots are amazing. We recommend the frying pan and highly HIGHLY recommend the spider hall farm stand (get the apple cobbler). Nonetheless the cottage is truly amazing and a perfect get away. "
The price is AED 1,107
AED 1,341 total
includes taxes & fees
18 Jul - 19 Jul
Cottage Located on the Patuxent River!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Marina

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

10.0 out of 10, Exceptional, (11)
"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
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher

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

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

9.2 out of 10, Wonderful, (25)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
On the beach

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

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AED 661
AED 1,080 total
includes taxes & fees
28 Jul - 29 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Terrace/patio

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!
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (250)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (4)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

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
Exterior

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
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (160)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
North Beach Cottage - Walk to Chesapeake Bay
Interior

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
Charming Waterfront Cottage Retreat near St. Michaels
Fridge, microwave, oven, stovetop

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (7)
"Our stay at this beautiful cottage was truly unforgettable! The space was clean, cozy, and well-appointed, with every detail carefully considered. Nestled right on the water’s edge, every inch of the house was tastefully decorated and had all the amenities you could ask for. The tasteful decor, fully stocked kitchen, and comfortable bed made us feel right at home from the moment we arrived.The hosts went above and beyond to make this an enjoyable stay, with excellent communication and thoughtful...
Charming Waterfront Cottage Retreat near St. Michaels
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!
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, (7)
"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
Enchanting West River Retreat
Outdoor dining

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
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, (45)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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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