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!
9.4 out of 10, Exceptional, (30)
"This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night."
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, (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
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
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Beautiful Bayfront with Sanctuary Private Beach
Outdoor dining
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (10)
"House was exactly as advertised and expected. Would stay agian for sure"
The price is ￥37,325
per night
Jun 9 - Jun 10
Beautiful Bayfront with Sanctuary Private Beach
Cottage near the Bay
Private kitchen | Fridge, microwave, oven, stovetop
Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is ￥14,055
per night
Jun 6 - Jun 7
Cottage near the Bay
Waterfront 3 bedroom condo. Spring is here!
Outdoor pool
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (20)
"Very relaxing time. The condo was beautiful"
Waterfront 3 bedroom condo. Spring is here!
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!
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, (46)
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
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, (6)
"Gorgeous location on the Great Wicomico!! Beautiful home with both a rustic feel and lovely modern additions. We brought our boat and the cove on Cole’s Creek was well protected with deep water. Property grounds were so nice, lots of space, and gorgeous view! The owner was super supportive and very helpful with recommendations in the area. Highly recommend!!"
Virginia Retreat on Wicomico River w/ Dock!
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, (25)
"Beautiful! The home was very clean, and fully stocked with everything you'd need during your stay. Had a lot of fun visiting the nearby towns--definitely had the small-town atmosphere. The cell phone service presented a challenge though. The three of us whose carrier was Verizon had no problem at all, but the other party who had another carrier was unable to get a connection unless we went closer to town. Something to consider. Also, we were unable to get local channels/cable on the TV. Used...
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Rock Hall on the water
Lake
Rock Hall on the water
9.4 out of 10, Exceptional, (42)
"We were scouting this house as a potential place to bring friends, and while we really liked the house there are a few things we noticed that might make us hesitant to bring a larger group. The ground floor was badly in need of vacuuming and there was hair in the shower drain. We never could connect to internet and had no cell service so couldn't even let anyone know. Finally, the water has a highly sulfur odor. Overall it seemed no-one had been in the house in a while and it needed some more...
Rock Hall on the water
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"
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
**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**
Quaint Island Getaway
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Smart TV, books
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 out of 10, Exceptional, (10)
"Just as advertised!!!! Highly recommend!!"
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Panoramic Waterfront Retreat: Big Game Room, Private Dock, Pedal Boat, 4 Kayaks!
Game room
Panoramic Waterfront Retreat: Big Game Room, Private Dock, Pedal Boat, 4 Kayaks!
10.0 out of 10, Exceptional, (34)
"The home was exactly as described. Just pack a bag and everything else is there. Fully equipped property in a quiet location. The only thing I will add is the master bed was smaller than desired, otherwise everything was perfect! We would love to return at another time when the temps are warmer."
Panoramic Waterfront Retreat: Big 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, (17)
"Everything at the property was as advertised. Just bring the fam and food and everything else is taken care of. Really enjoyed the added touches like providing a s'mores kit, or having cold drinks already available upon check in as provided by host. Don't let this one slip away and enjoy your stay at the kozy kottage"
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
Fridge, microwave, stovetop, dishwasher
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
10.0 out of 10, Exceptional, (88)
"Stay was lovely."
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
BEACH COTTAGE BY THE SEA....
Fitness facility
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....
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.

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!
9.4 out of 10, Exceptional, (30)
"This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night."
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, (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
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.

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:

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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?

Beautiful Bayfront with Sanctuary Private Beach : This vacation home near Smith Island has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Smith Island?

With 4 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

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

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

5/5 Excellent
Great fishing vrbo
"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"
A verified traveler stayed at IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Posted 16 hours ago
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK