Smith Island Vacation Rentals

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In two weeks
Sep 12 - Sep 14
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Dec 19 - Dec 21

Vacation Rentals in Smith Island

Our top choices for Smith Island vacation rentals

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!
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Smart TV, fireplace, table tennis, books

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 ￥33,082
￥50,808 total
includes taxes & fees
Sep 1 - Sep 2
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Interior

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (19)
"Calm island living. No beach, no booze, nice kind people. Good food. Lazy relaxed atmosphere. "
Pet-Friendly Smith Island Cottage w/ Golf Cart!
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, (18)
"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
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

10.0 out of 10, Exceptional, (1)
"Amazing adventure! Peaceful! Beautiful! Privacy! Gourmet Kitchen! The house is set back from the neighborhood on a large lot. The decks are new and comfortably furnished. We cooked breakfast and dinner for 3 days and the well-equipped kitchen was perfect. Our days started and ended with gourmet meals, on the deck, emersed in the salt marsh. We explored the creeks, guts, and islands all around Ewell, Rhodes Point and Tylerton. Rich and Dani helped coordinate a private charter boat to bring our...
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is ￥11,911
￥27,745 total
includes taxes & fees
Sep 1 - Sep 2
Cottage near the Bay
**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**
BEACH COTTAGE BY THE SEA....
Property grounds

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....
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!
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (118)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (72)
"Everything was as advertised. Clean and tidy. Easy to find. Had everything we needed while visiting some state parks. Kids loved the beach and already asked to go back"
Private Beach Front Getaway at The Sunshine Beach Cottage.
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
"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included
Fridge, microwave, stovetop, coffee/tea maker

"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

9.8 out of 10, Exceptional, (67)
"We made last minute plans and were happy with our decision to stay at Mary’s place. It was big enough for our family including our two teenage daughters. The location is quiet and peaceful. The home was clean and had everything we needed!"
"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included
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
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, (218)
"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!
Charming 3-bedroom house on PRIVATE BEACH in lovely Heathsville
Sun loungers, beach towels

Charming 3-bedroom house on PRIVATE BEACH in lovely Heathsville

10.0 out of 10, Exceptional, (2)
"A perfect multigenerational family getaway. A nicely renovated property with first class furnishings and amenities. Main floor bedroom and full bath ideal for family with children or those that can’t use stairs. Private sandy beach easily accessible perfect for wading or swimming (kids loved it!). Owner provided beach chairs, canopy, umbrella and beach toys for kids were high quality and in great condition. Easy driving from Richmond or DC. Lovely and peaceful location. Highly recommended!"
Charming 3-bedroom house on PRIVATE BEACH in lovely Heathsville
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
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Outdoor dining

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
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
Interior

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

9.6 out of 10, Exceptional, (126)
"Beautiful location in a great setting to spend time with family. So appreciated that the house was pet friendly and the neighbors were so nice."
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
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

Search for holiday rentals in Smith Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Smith Island using one of the methods below:

  • View our selection of featured holiday rentals in Smith Island
  • Use the map to find apartments and other holiday homes in the Smith Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Smith Island while they last

Look no further and take a look at our great range of rental properties in Smith Island!

Frequently asked questions

Can I find vacation rentals in Smith Island?

Yes, you can find vacation rentals close to the most popular attractions in Smith Island, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Smith Island?

Historic home on Smith Island w/ dock!: This highly rated vacation home rental in Smith Island is located on the waterfront and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books. Our travelers also rate Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart as a favorite home for rent in Smith Island.

How many vacation rentals are there in Smith Island?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Smith Island stay.

What can I see and do in Smith Island?

Smith Island and Horse Hammock are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Tylerton County Dock and Terrapin Sand Point.

What are vacation rentals like in Smith Island?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Smith Island. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.