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Compare 47 Cottages in Sunderland with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Property grounds
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our long weekend stay. We spent great time together in the cozy and spacious living room, as well as enjoying the nice waterfront outdoor areas. The house is unique, well equipped, very clean, and with great attention to details in every room. Host was very proactive and responsive in the communication. Canoes and bikes are available, what we enjoyed. Views from the house were wonderful, including a beautiful sunrise. It was a very relaxing family weekend and we can’t wait...
The price is SAR 1,686
SAR 3,533 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (203)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area
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
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, (33)
"A beautiful stay on the Chesapeake."
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
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Waterfront property with private boat ramp and new dock!
Exterior
Waterfront property with private boat ramp and new dock!
9.6 out of 10, Exceptional, (8)
"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!
North Beach Cottage - Walk to Chesapeake Bay
North Beach Vacation Rental | 3BR | 2BA | 1,304 Sq Ft | Steps Required to Access
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (27)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Outdoor dining
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, (12)
"What a wonderful bungalow! Convenient location for Calvert Cliffs hiking, Cove Point lighthouse, PAX Naval Air Museum and Calvert Marine Museum. We really enjoyed the screened porch for relaxing and our meals. Special treat with the coffee bar. Kitchen was stocked with everything we needed. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (156)
"Great cottage along a quiet road in a private setting. This is just what my family was looking for to escape the busy weekend in Annapolis. Will not hesitate to schedule future stays at this home."
The Yellow Cottage on Harness Creek
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter
Updated North Beach Cottage: Pet Friendly!
10.0 out of 10, Exceptional, (11)
"We came into town over the weekend for a family funeral. The house was perfect. So cute and clean. Location is great. House has everything you need and comfy beds. Would definitely stay here again."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Living area
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living area
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is SAR 526
SAR 1,087 total
includes taxes & fees
17 Nov - 18 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Cozy Cottage with access to and partially obstructed views of the bay.
Exterior
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cottage Located on the Patuxent River!
Room
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is SAR 1,221
SAR 1,473 total
includes taxes & fees
16 Nov - 17 Nov
Cottage Located on the Patuxent River!
Family-friendly Chesapeake Beach House With Deck!
Living area
Family-friendly Chesapeake Beach House With Deck!
3.0 star property
6.0 out of 10, (1)
Family-friendly Chesapeake Beach House With Deck!
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 751
SAR 1,227 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H
Inviting cottage beside wooded lot for privacy.
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H
9.6 out of 10, Exceptional, (90)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H
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 Sunderland

Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (47)
"Everything close by!"
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.

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