Search Smith Island Cottage Rentals from CA $225

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Browse Select Smith Island Cottages

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (72)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.

BEACH COTTAGE BY THE SEA....

9.8 out of 10, Exceptional, (30)
"A beautiful little cottage with a beautiful beach front access and plenty of amenities."
BEACH COTTAGE BY THE SEA....

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"
Hays Beach House - Hot Tub - Private Beach

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (118)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

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!

9.8 out of 10, Exceptional, (19)
"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!

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

Walk to Beach: Pet-Friendly Gem in Scotland!

10.0 out of 10, Exceptional, (4)
"Great space for a short stay getaway!"
Walk to Beach: Pet-Friendly Gem in Scotland!

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"The house is absolutely beautiful and the view is spectacular ! If by chance you forget to bring something with you dont worry they have it all right down to the lotion. The neighbors are great too ! Loved our stay."
Waterfront Maryland Retreat w/ Dock & Bay View!

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

9.6 out of 10, Exceptional, (4)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is CA $225
CA $489 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

3-bedroom water-front cottage on 2 1/2 secluded acres near Reedville,VA

10.0 out of 10, Exceptional, (12)
"Can’t say enough good things about this cottage. Great location and accommodations!"
3-bedroom water-front cottage on 2 1/2 secluded acres near Reedville,VA

Cheery Waterfront Cottage w/Boat Dock

10.0 out of 10, Exceptional, (8)
"Very nice place with convenient access to a small private beach and dock. The property was clean, well maintained and stocked with all the essentials."
Cheery Waterfront Cottage w/Boat Dock

"Dragonfly" Waterfront Cottage on Chesapeake Bay

2.5 star property
10.0 out of 10, Exceptional, (2)
"Great getaway location right on th4e water. Highly recommended"
"Dragonfly" Waterfront Cottage on Chesapeake Bay

'river's Edge Retreat With Kayaks & River Access!

3.0 star property
'river's Edge Retreat With Kayaks & River Access!

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10.0 out of 10, Exceptional, (120)
"Thanks for a great stay at Hay's Beach. We loved your little get-away home and with a second child starting at St. Mary's College of Maryland next year, we'll be sure to be back a time or two. "
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

10.0 out of 10, Exceptional, (17)
"Loved every minute of our stay! The house was so clean and well equipped. Couldn’t beat the location to the beach and the beauty of all the scenery! We will definitely be back!"
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

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!

Charming Waterfront 3-Bedroom Cottage with Hot Tub, Kayaks, Workspace, Fishing

9.4 out of 10, Exceptional, (3)
"Wonderfully relaxing weekend on the water with the kids. So peaceful. Property gorgeous. Photos spot on. So many cozy hangouts in the house. Games, Roku TV. Fully functional kitchen, for those cooks out there. Would recommend just grabbing your groceries at Food Lion in the way in from town, and then slow down and enjoy!"
Charming Waterfront 3-Bedroom Cottage with Hot Tub, Kayaks, Workspace, Fishing

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!

Sunrise and Sunset at the Bay

10.0 out of 10, Exceptional, (23)
"beautiful place with waterfront stay, plus sunrise and sunset view! Had a great time"
Sunrise and Sunset at the Bay
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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Top Smith Island Hotel Reviews