Smith Island Vacation Rentals

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Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Smith Island Vacation Homes

Our top choices for Smith Island vacation homes

Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is CA $111
CA $259 total
includes taxes & fees
Sep 3 - Sep 4
Cottage near the Bay
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Outdoor pool, a heated pool

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

9.6 out of 10, Exceptional, (92)
"This is a wonderful property to visit. It was in a great location with beautiful views. The property is clean, the host was friendly and accommodating. It is a location that I would definitely recommend and go back to visit again."
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
**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, (192)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Panoramic Waterfront Views: Firepit, Private Dock, Pedal Boat, Gameroom, Kayaks!
Game room

Panoramic Waterfront Views: Firepit, Private Dock, Pedal Boat, Gameroom, Kayaks!

9.8 out of 10, Exceptional, (52)
"I run a nonprofit for veterans five of us came down really enjoyed our stay. The house was perfect for what we needed. Would recommend it to anyone."
Panoramic Waterfront Views: Firepit, Private Dock, Pedal Boat, Gameroom, Kayaks!
Newly updated 3 bedroom cottage with Solo Stove fire pit
Smart TV

Newly updated 3 bedroom cottage with Solo Stove fire pit

9.6 out of 10, Exceptional, (9)
"This was a nice quiet place for family to enjoy."
The price is CA $124
CA $334 total
includes taxes & fees
Sep 2 - Sep 3
Newly updated 3 bedroom cottage with Solo Stove fire pit
Walk to Main Street: Family-Friendly Crisfield Gem
Fridge, microwave, stovetop, dishwasher

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Exterior

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

2.0 star property
8.0 out of 10, Very good, (5)
"I did do some cooking and did not find a sheet pan."
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Bay Front Small Contemporary
On the beach, sun loungers

Bay Front Small Contemporary

9.8 out of 10, Exceptional, (111)
"Perfect spot for a quiet Easter weekend with books and the sound of water while sitting in the Adirondack chairs each day. You won’t regret this stay, will definitely come back! "
Bay Front Small Contemporary
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
Property grounds

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

10.0 out of 10, Exceptional, (217)
"Went for spring break - weather was colder than we hoped for but a beautiful property with all the amenities! Very peaceful, owners attentive. Would definitely go back again!"
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
When you want to get away from everything Magnolia shores 2 acres of tranquility
Outdoor pool, a heated pool

When you want to get away from everything Magnolia shores 2 acres of tranquility

10.0 out of 10, Exceptional, (71)
"Nice property, clean. Perfect for a getaway !"
When you want to get away from everything Magnolia shores 2 acres of tranquility
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Property grounds

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is CA $309
CA $474 total
includes taxes & fees
Sep 9 - Sep 10
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Outdoor dining

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

9.6 out of 10, Exceptional, (40)
"Adorable home with an amazing view from any window! We kayaked right from the dock. The view is why you stay here! Breathtaking! Management responded quickly. We would definitely stay again and recommend to anyone who loves the water and views. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
River front Home built in 2021 with Private Pier
Fridge, microwave, oven, stovetop

River front Home built in 2021 with Private Pier

10.0 out of 10, Exceptional, (10)
"Great stay"
River front Home built in 2021 with Private Pier
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Outdoor dining

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Reedville Retreat, waterfront w/ private dock &outdoor sink-for fishing/crabbing
Exterior

Reedville Retreat, waterfront w/ private dock &outdoor sink-for fishing/crabbing

10.0 out of 10, Exceptional, (14)
"Excellent place, so convenient for us. The 4th of July activities were at our front door, was great watching races, parades, aand fireworks, all while sitting on the front porch."
Reedville Retreat, waterfront w/ private dock &outdoor sink-for fishing/crabbing
Bay Hideaway • Peaceful Vibes & Semi-Private Beach at "Bliss on the Bay"
Fridge, microwave, oven, stovetop

Bay Hideaway • Peaceful Vibes & Semi-Private Beach at "Bliss on the Bay"

9.4 out of 10, Exceptional, (11)
"What a wonderful location off the beaten path to spend a couple days away with the family! Great semi private beach that we had mostly to ourselves, and a very clean house with amenities that the kids loved! We will be coming back!"
Bay Hideaway • Peaceful Vibes & Semi-Private Beach at "Bliss on the Bay"
Waterfront Bay Home, Amazing Water Views, with Private Saltwater Pool
Pool

Waterfront Bay Home, Amazing Water Views, with Private Saltwater Pool

10.0 out of 10, Exceptional, (14)
"The perfect place for our family vacation."
Waterfront Bay Home, Amazing Water Views, with Private Saltwater Pool
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, (74)
"We had a great time. Private beach, spacious house, kayaks!"
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
18-Acre Waterfront Sanctuary: Peace & Privacy
Terrace/patio

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
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

Find out more about Smith Island

Find out more about Smith Island

Smith Island Vacation Homes information

Number of reviews
327
Accommodation
89 Vacation Homes
Lowest Price
CA $111
Highest Price
CA $309

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