Holiday Homes in Smith Island

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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Featured Holiday Homes in Smith Island

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Dining

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
9.4 out of 10, Exceptional, (3)
"The house worked out good for 4 hunters."
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Waterfront Scotland Beach Retreat w/ Private Beach
On the beach

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
On the beach

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Miscellaneous

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2.0 star property
6.0 out of 10, (2)
"I did do some cooking and did not find a sheet pan."
The price is AU$465
includes taxes & fees
25 Jan - 26 Jan
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
On the beach

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
Virginia Retreat on Wicomico River w/ Dock!
Interior

Virginia Retreat on Wicomico River w/ Dock!

10.0 out of 10, Exceptional, (16)
"My mom didn’t want to leave. Beautiful family retreat. Quiet and restful. "
Virginia Retreat on Wicomico River w/ Dock!
Bay House with Amazing View & Swimming Pool (open May- Sept.)
On the beach

Bay House with Amazing View & Swimming Pool (open May- Sept.)

9.8 out of 10, Exceptional, (116)
"It is a dream place; my family and I had a great time, thanks to Jenn's prompt response. It is a very comfortable place and well-equipped for whatever one needs. I'll try to look them up on Facebook to follow them. Thank you very much for everything; it is a beautiful place with amazing views "
Bay House with Amazing View & Swimming Pool (open May- Sept.)
18-Acre Waterfront Sanctuary: Peace & Privacy
Aerial view

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
Waterfront Marion Station Retreat w/ Private Dock!
Fridge, microwave, stovetop, dishwasher

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!
Secluded River Front Cottage
Beach

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Bay Estate by AvantStay | Waterfront, Private Pond
On the beach

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond
Chesapeake Bay and Lakefront home with Private Beach
Interior

Chesapeake Bay and Lakefront home with Private Beach

10.0 out of 10, Exceptional, (36)
"This was the most epic of summer trips. This lovely home, not a house a home, gave our family time to connect, unwind and enjoy the wonders of the bay. Even when the weather was not sunny beach weather, we loved the gathering spaces to play games and enjoy family time. Our hosts were lovely and when we met a neighbor and her lovely dogs they were just as lovely. Just heaven"
Chesapeake Bay and Lakefront home with Private Beach
Historical Queen Anne on Main Street Reedville!
Fridge, microwave, oven, stovetop

Historical Queen Anne on Main Street Reedville!

10.0 out of 10, Exceptional, (7)
"Hope to stay there again next year!"
Historical Queen Anne on Main Street Reedville!
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball in Onancock
Miscellaneous

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball in Onancock

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball in Onancock
Serene waterfront getaway, fire pit, patio w/grill, nature, dog friendly
Property grounds

Serene waterfront getaway, fire pit, patio w/grill, nature, dog friendly

10.0 out of 10, Exceptional, (2)
"Well appointed and very clean. Property manager and owners added special touches to welcome us. Thank you for opening your house to us. We will be back."
Serene waterfront getaway, fire pit, patio w/grill, nature, dog friendly
Private Creek Retreat w/ king suite, firepit, kayaks
Exterior

Private Creek Retreat w/ king suite, firepit, kayaks

10.0 out of 10, Exceptional, (5)
"This is beautifully decorated, clean, and a wonderful spot to get away."
Private Creek Retreat w/ king suite, firepit, kayaks
Waterfront Reedville Home w/ Private Dock!
Fridge, microwave, stovetop, dishwasher

Waterfront Reedville Home w/ Private Dock!

10.0 out of 10, Exceptional, (15)
"This was an ideal solution to having all the adult children, grandchild and in-laws close to us for the holidays! House was lovely, well appointed with everything that was needed for a comfortable and worry free visit. Will be back!"
Waterfront Reedville Home w/ Private Dock!
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Outdoor dining

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

9.8 out of 10, Exceptional, (32)
"Very nice and quiet. We were there end of December. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (183)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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 Smith Island

Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior

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

10.0 out of 10, Exceptional, (15)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
Property grounds

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

10.0 out of 10, Exceptional, (1)
"As many reviewers say, Smith Island is not a hot spot teaming with places to go. We knew this when booking. We brought our cameras, our water colors to paint, books, knitting, cards.... we had a WONDERFUL time. The cottage was beautiful and had everything we needed. The host even supplied us with board games and bug spray. We walked the length of the island several times and spent most mornings with our binoculars and cameras birding. If you want to relax and can entertain yourself it is a...
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
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.