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Compare 55 Cottages in Sunderland with updated reviews, rates, and availability.

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.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland

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

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

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (1)
"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

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

10.0 out of 10, Exceptional, (8)
"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

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (242)
"If you’re looking for a remote location on the water, this is it. House was clean, hosts were nice. No complaints. "
Family and Pet-Friendly, Waterfront with Pier

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (14)
"It was very clean and not cluttered. I felt it had all the essentials, however, lacked closet space in the bed-rooms. Definitely would stay there again."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

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!

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again. "
Enchanting West River Retreat

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!

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

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
The price is AED 1,539
AED 3,340 total
includes taxes & fees
10 Mar - 11 Mar
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

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

10.0 out of 10, Exceptional, (42)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is AED 588
AED 1,125 total
includes taxes & fees
10 Mar - 11 Mar
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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.

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 1,185 total
includes taxes & fees
10 Mar - 11 Mar
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

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

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 Sunderland

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage

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.

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
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.

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