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Browse Select Deal Island Cottages

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (48)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (17)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Dog-Friendly Westover Cottage w/ River Access!

10.0 out of 10, Exceptional, (11)
"We stayed for a weekend - wished it would've been longer! Great, quiet family home with lots of character in a beautiful spot by the river. Kitchen is well equipped with all that's needed. Everything is very organized and clean. We enjoyed kayaking and the campfire in the evening. Thanks Kelly - we'll try to come back again soon."
Dog-Friendly Westover Cottage w/ River Access!

Pet-friendly Smith Island Cottage w/ Golf Cart!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
Pet-friendly Smith Island Cottage w/ Golf Cart!

Dog-friendly Westover Cottage w/ River Access!

3.0 star property
8.0 out of 10, Very good, (1)
"It was great and family enjoyed our relaxation "
Dog-friendly Westover Cottage w/ River Access!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The most well stocked property we've ever stayed! everything from extra phone chargers to blankets, tons of games and the kitchen as well."
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Walk to Main Street: Family-friendly Crisfield Gem

3.0 star property
Walk to Main Street: Family-friendly Crisfield Gem

Private Beach & Fishing Pier: Wicomico River House

3.0 star property
Private Beach & Fishing Pier: Wicomico River House

1 Mi to Boat Ramp: Peaceful Deal Island Home!

3.0 star property
1 Mi to Boat Ramp: Peaceful Deal Island Home!

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!

Waterfront Maryland Retreat w/ Dock & Bay View!

3.0 star property
Waterfront Maryland Retreat w/ Dock & Bay View!

Year Round Playground - Rare Rustic-Modern Getaway

2.0 star property
Year Round Playground - Rare Rustic-Modern Getaway

Riverfront Gem w/ Fire Pit in Eden

3.0 star property
Riverfront Gem w/ Fire Pit in Eden

Waterfront Marion Station Retreat w/ Private Dock!

3.0 star property
Waterfront Marion Station Retreat w/ Private Dock!

Updated Home - Walk to Salisbury University!

3.0 star property
Updated Home - Walk to Salisbury University!
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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