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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 352 Vacation Homes in Sunderland with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"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!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

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
View from property

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
On the beach

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
Interior

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
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Everything was perfect and the host was very kind! Would definitely recommend, especially for anyone staying in the area for a wedding."
The Lazy Crab Beach House - Free beach passes
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

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 SAR 361
SAR 1,039 total
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 732
SAR 1,407 total
includes taxes & fees
8 May - 9 May
The Cottage
7 mins away from Downtown Annapolis
Outdoor dining

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"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
Fridge, microwave, oven, stovetop

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~
On the beach, beach towels

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
Interior

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

9.8 out of 10, Exceptional, (6)
"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 SAR 375
SAR 1,318 total
includes taxes & fees
21 Apr - 22 Apr
Wright's Cottage- Pet's Welcome & EV Charging
Cozy Cottage 3 beds 2 baths
Outdoor dining

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
Outdoor dining

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
Beach

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!
Fridge, microwave, oven, stovetop

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 SAR 1,032
SAR 1,909 total
includes taxes & fees
12 May - 13 May
Beautiful Waterfront Retreat in Cambridge!
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

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!
Property grounds

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!
Private Cottage on gated estate
Beach

Private Cottage on gated estate

10.0 out of 10, Exceptional, (22)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
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
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"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
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (24)
"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
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"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
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.