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Compare 353 Vacation Homes in Sunderland with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
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)
"Needed a little quiet time, and the fresh air. Had a nice time. The house is clean,stocked with basic essentials. The beds are comfortable, that is super important to me, I also enjoyed the color choices and decorations. Tracy was prompt and thorough. I’d stay again . "
Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
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)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
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)
"Enjoyed all 6 nights in this property. Manager was very responsive to all questions about the neighborhood and property. Kitchen was well stocked with pots and pans in the yard was nice to let the dog run around. "
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)
"Clean, Spacious, and exactly as advertised! "
The price is AED 251
AED 889 total
includes taxes & fees
28 Apr - 29 Apr
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)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
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)
"The property is beautiful. The house is spacious and has comfortable beds and excellent bathrooms. There were some things that could make a stay so much better. The bedrooms need at least one chair. Although there were books in a drawer with directions for the high end appliances, each one should have a quick explanation on usage next to it. The information said the table seated 8 and yet there were only six chairs! A putting green was described and even showed a picture of one in the original...
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)
"Our girls' weekend at this VRBO was absolutely perfect! From the moment we walked in, we were blown away by the gorgeous interior and stunning views. The house was fully equipped with everything we needed, making our stay incredibly comfortable and convenient. The hot tub was a huge hit and added an extra touch of luxury to our getaway.The beds were incredibly comfortable, and the entire house was spotlessly clean upon our arrival. We truly appreciated the attention to detail.The host was...
25-50% Off~Private Beach~Hot Tub~Fire Table~

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

9.8 out of 10, Exceptional, (8)
"Super cute, very peaceful. Would stay again "
The price is AED 367
AED 1,286 total
includes taxes & fees
28 Apr - 29 Apr
Wright's Cottage- Pet's Welcome & EV Charging

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (3)
"The house is lovely, comfortable, clean. It is on the Chesapeake, and the back deck is just wonderful for enjoying the beautiful views of the bay and sunset. We loved the house, and the people on Tilghman Island were very nice. The house is perhaps a 20 minute drive to St. Michael's, which was a great outing for the afternoon. And, Two if by Sea, the restaurant within a couple of blocks of the house, had a wonderful breakfast. We would love to come back. "
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 perfect Thanksgiving. House was just right for family of three although more people would have been fine too. Lived the crab shack and played lots of pool and ping pong. Kitchen well stocked. Owners were prompt in responding to any questions. We would come back in a heartbeat."
The price is AED 1,010
AED 1,892 total
includes taxes & fees
29 Apr - 30 Apr
Beautiful Waterfront Retreat in Cambridge!

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

9.6 out of 10, Exceptional, (17)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
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)
"An absolutely beautiful, architecturally fascinating, spotlessly clean, well stocked home with views that go on for literally miles. We spent a late winter weekend there with a fire roaring in the fireplace and mussels on the stove. Hosts were exceptionally responsive and very attentive. Highly recommended. One of the best experiences we've ever had in home rentals! "
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, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (245)
"This was the perfect location and property for our family. I only wished we booked a longer trip! The amenities inside and out, and the friendliness of our hosts made this a great way to relax away from the Beltway and get out on the water. The kids didn’t want to leave "
Family and Pet-Friendly, Waterfront with Pier

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"Rainy weather limited activities but would return to property"
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.