Vacation Homes in Smith Island, MD

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Top Vacation Homes in Smith Island

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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.

Top hotels in Smith Island

Find the Best Vacation Homes in Smith Island

Why book a vacation home in Smith Island?

Vacation homes in Smith Island make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Smith Island?

Private Smith Island rental homes range between - per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Smith Island vacation home rentals. You might look for Smith Island rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Smith Island offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Smith Island?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Smith Island. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Smith Island hotels and vacation homes that best suit your stay. We also have deals for flights, and Smith Island car rentals. You’ll save even more when you bundle your items into a Smith Island vacation package!

How many vacation homes are available to book in Smith Island?

There are 90 rental homes in Smith Island. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Smith Island?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Smith Island Vacation Homes essential information

Accommodation
90 Vacation Homes
Lowest Price
Highest Price
Popular accommodation
Cottage near the Bay, **FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**, Historic home on Smith Island w/ dock!, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Get away to relax on Smith Island in the Chesapeake Bay with golf cart included , July 4th available! Waterfront getaway! Fish and crab from private dock!, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront! , Bay House with Amazing View & Swimming Pool (open May- Sept.), Waterfront Getaway: Kayaks, Paddle Board, Fishing!, Virginia Retreat on Wicomico River w/ Dock!, When you want to get away from everything Magnolia shores 2 acres of tranquility, Waterfront Reedville Home w/ Private Dock!