Smith Island Vacation Rentals

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Vacation Rentals in Smith Island

Historic home on Smith Island w/ dock!
Beach
Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, (31)
"During our stay at The Pearl, we encountered our own boat issues, but the hosts were extremely helpful. Their communication was above and beyond!! The people on the island were also extremely helpful, and they went out of their way to help in any way they could. They all truly wanted us to have a great experience on Smith Island. The Pearl had everything we needed for our stay, and there was plenty of room for us. We took our pet Corgi and she felt right at home and loved the big yard! We CANNOT...
Historic home on Smith Island w/ 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
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, (12)
"Kim and Mickey made us feel very welcomed and the waterfront home was immaculate with a well equipped kitchen and beautiful flowers! We had a wonderful visit! Thanks again. Julie"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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Waterfront Reedville Home w/ Private Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (8)
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
Waterfront Reedville Home w/ Private Dock!
Cottage near the Bay
Private kitchen | Fridge, microwave, oven, stovetop
Cottage near the Bay
8.8 out of 10, Excellent, (15)
"The owner was quick to respond, informative, and polite. The property did the job we were asking from it by being near by our family, close to the bay, and being pet friendly. I was not impressed by the cleanliness, but it was not out right dirty or unsanitary. You get what you pay for. Over all we were pleased with our stay!"
The price is $90
$198 total
includes taxes & fees
Jun 25 - Jun 26
Cottage near the Bay
Beautiful Bayfront with Sanctuary Private Beach
Outdoor dining
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (12)
"The house is beautiful and very clean, not as isolated as we thought based on listing. View amazing, needed lots of bug spray- but were notified of this by owner ahead of time, so it was all good."
The price is $249
$407 total
includes taxes & fees
Jun 25 - Jun 26
Beautiful Bayfront with Sanctuary Private 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, (49)
"Beautiful little house right on the beach of the Chesapeake. Loved it. Everything was great and we will definitely be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Property grounds
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
10.0 out of 10, Exceptional, (26)
"It was great except tv did not work in one house. We were disappointed. The add said paddle boats and they were not there. It was a lovely home and the view was breathtaking"
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
Outdoor pool
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
10.0 out of 10, Exceptional, (21)
"The condo was beautiful and exceptional! We had everything we needed and more. It was obvious that time had been taken to think through the processes of what people may need. We recommend this property! We thoroughly enjoyed the balcony and screened porch for morning coffee, and happy hour. We were there Monday through Thursday and the town was very quiet. We had jumbo crabs from Linton’s, and took the ferry out to Tangier Island. The cream chip beef “From Scratch” Is very good. On Tangier...
Waterfront 3 bedroom condo. Summer has arrived, pool is open!
Come, sit back and relax at the "Catch of the Bay"
Terrace/patio
Come, sit back and relax at the "Catch of the Bay"
10.0 out of 10, Exceptional, (3)
"It was very good, very clean and cozy. I would recommend the place for sure."
Come, sit back and relax at the "Catch of the Bay"
Virginia Retreat on Wicomico River w/ Dock!
TV, fireplace, DVD player, foosball
Virginia Retreat on Wicomico River w/ Dock!
10.0 out of 10, Exceptional, (8)
"The house was great, had beautiful views, and lots of room to stretch out. Very responsive host as well. We enjoyed our stay!"
Virginia Retreat on Wicomico River w/ Dock!
Bay Front Small Contemporary
Aerial view
Bay Front Small Contemporary
9.8 out of 10, Exceptional, (90)
"This property was so clean, the views out the windows were spectacular, and the water is right there! I greatly enjoyed the kayak and my dog just loved the privacy he had to play in the water. The host was extremely quick to respond and was one of the nicest hosts we've ever had. Highly recommend this spot and we can't wait to return!"
Bay Front Small Contemporary
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
View from property
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
10.0 out of 10, Exceptional, (1)
"This condo was spacious and lovely. Nicely decorated and very pristine. The view was amazing as well as the sunsets! Enjoyed the delightful pool overlooking the water and marina. Definitely peaceful and we had it practically to ourselves! The owner was friendly, helpful and easy to communicate with. An ideal place to visit and unwind. Highly recommend!!"
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake 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, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Rock Hall on the water
Lake
Rock Hall on the water
9.4 out of 10, Exceptional, (43)
"We had a great time in this home. It was extremely clean and perfect for our family. The huge yard was amazing. We had coffee on the porch as the sun came up. Very quiet and private. We definitely will go back!"
Rock Hall on the water
Secluded Waterfront Retreat: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!
Game room
Secluded Waterfront Retreat: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!
10.0 out of 10, Exceptional, (35)
"My husband and infant twins enjoyed a relaxing stay in Reedville- the house is clean and welcoming and had everything we needed. The view is great and we enjoyed the kayaks. We enjoyed local seafood for dinner and a drive to kilmarnock. Hope to come back soon!"
Secluded Waterfront Retreat: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
Aerial view
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
10.0 out of 10, Exceptional, (19)
"For 2 busy professionals, staying at this property was restorative, delightful and invigorating. We stopped by a local farm, rode bikes & played golf, rose to the sunrise over the water and took sunset photos on the dock (embarrasing but true) and enjoyed the local crab/seaside fare. It is a casual, rural setting with every detail considered and amazing host communication. A+"
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
BEACH COTTAGE BY THE SEA....
Property grounds
BEACH COTTAGE BY THE SEA....
9.8 out of 10, Exceptional, (17)
"We loved this quiet property, right on the water. The house was clean and perfect for my mom and me. I didn’t use the kitchen but it was stocked with a lot of stuff. Towels for the beach were provided, along with chairs for sitting on the beach. There is a rinse off area in the back of the house, but to turn the water on you have to go in front of the house. I absolutely would return. "
BEACH COTTAGE BY THE SEA....
Idyllic Waterfront Home w/ Game Room, Shared Dock
Property grounds
Idyllic Waterfront Home w/ Game Room, Shared Dock
9.8 out of 10, Exceptional, (16)
"Everything was great about the place. Only downside was the water pressure was low at times so we had to cordinate taking showers but that was a small issue. Overall would stay again"
Idyllic Waterfront Home w/ Game Room, Shared Dock
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Smart TV, fireplace
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, (101)
"The condo was perfect. Checkin was easy, was as described and the view was amazing. Would recommend to anyone looking for a relaxing getaway"
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Don't see what you're looking for?
See all available properties in Smith Island
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.

Smith Island Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Smith Island private vacation homes
Known landmarks
J. Millard Tawes Museum
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Smith Island you may be interested in

Historic home on Smith Island w/ dock!
Beach
Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, (31)
"During our stay at The Pearl, we encountered our own boat issues, but the hosts were extremely helpful. Their communication was above and beyond!! The people on the island were also extremely helpful, and they went out of their way to help in any way they could. They all truly wanted us to have a great experience on Smith Island. The Pearl had everything we needed for our stay, and there was plenty of room for us. We took our pet Corgi and she felt right at home and loved the big yard! We CANNOT...
Historic home on Smith Island w/ 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
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, (12)
"Kim and Mickey made us feel very welcomed and the waterfront home was immaculate with a well equipped kitchen and beautiful flowers! We had a wonderful visit! Thanks again. Julie"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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.

Everything you need to know about Smith Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smith Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smith Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smith Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smith Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Smith Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smith Island rentals

At Expedia, we put the best Smith Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Smith Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smith Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smith Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Waterfront Reedville Home w/ Private Dock!: This vacation home rental near Smith Island is located on the waterfront and has a selection of games, a barbecue grill, and air-conditioning 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.

How many vacation rentals are there in Smith Island?

With 3 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?

Explore the area and family-friendly sights such as Reedville Fishermen's Museum, or get out into nature at a spot like Smith Island. In the larger area, you’ll find Tangier Island and Point Lookout State Park.

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.

Recent reviews of Smith Island properties
Expedia verified reviews

Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.

5/5 Excellent
Everything was great!
"Beautiful little house right on the beach of the Chesapeake. Loved it. Everything was great and we will definitely be back!"
A verified traveler stayed at Private Beach Front Getaway at The Sunshine Beach Cottage.
Posted 2 days ago
Private Beach Front Getaway at The Sunshine Beach Cottage.