Sunderland Vacation Rentals

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Browse Select Sunderland Vacation Homes

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (53)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Would stay again."
The Lazy Crab Beach House - Free beach passes

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $95
CA $335 total
includes taxes & fees
Apr 28 - Apr 29
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (15)
"A warm and cozy property that can hold that big holiday gathering you want. Well stocked, comfortable, and full of what you need."
7 mins away from Downtown Annapolis

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (22)
"It was the perfect romantic getaway! "
25-50% Off~Private Beach~Hot Tub~Fire Table~

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (8)
"Great location. Small but perfect for myself, my daughter & our big goofy dog. Old house but well maintained and cozy, fenced back yard. Really enjoyed our stay!"
The price is CA $139
CA $485 total
includes taxes & fees
Apr 29 - Apr 30
Wright's Cottage- Pet's Welcome & EV Charging

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (3)
"What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer"
Time Stands Still At the Dock.

Cozy Cottage 3 beds 2 baths

9.8 out of 10, Exceptional, (78)
"Absolutely perfect, will stay here again and again when visting family in Maryland. "
Cozy Cottage 3 beds 2 baths

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

5 bedroom, 8 bed, 3 story house a block from beach

9.6 out of 10, Exceptional, (13)
"Everything went extremely smooth. Check in was easy. House was nice and clean. Had a lot of fun with the gaming stuff they had set up! The house had everything you could imagine and more! Owners were extremely nice and informative. Recommended good places to go and eat. Overall great experience and would definitely go again."
5 bedroom, 8 bed, 3 story house a block from beach

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (33)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is CA $381
CA $710 total
includes taxes & fees
May 1 - May 2
Beautiful Waterfront Retreat in Cambridge!

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (17)
"Very nice property, relaxing comforatable stay"
Bay views with kayaks, bikes, fire pit, crabbing and more

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (77)
"Beautiful place "
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
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

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (53)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (245)
"This is a beautiful site and the hosts were incredibly welcoming and hospitable. We highly recommend it to anyone looking for a place to stay in the area."
Family and Pet-Friendly, Waterfront with Pier

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"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.