Smith Island Vacation Rentals from AED 985: Search Short-Term Rentals

Q: 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 Summer is here on Smith Island! Come out and enjoy a great season on the Bay as a favorite home for rent in Smith Island.

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Our top choices for Smith Island vacation rentals

1. Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Smith Island

Samantha J.

AED 1,322 total

includes taxes & fees

7 Aug - 8 Aug

2. Cottage near the Bay

Crisfield

Pamela

AED 689 total

includes taxes & fees

16 Aug - 17 Aug

3. Tangier Escape, great place get away from it all on Deal Island, MD.

Deal Island Historic District

Jennifer P.

AED 903 total

includes taxes & fees

13 Aug - 14 Aug

4. Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville

Myranda R.

AED 985 total

includes taxes & fees

10 Aug - 11 Aug

5. Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom

Reedville

AED 1,334 total

includes taxes & fees

10 Aug - 11 Aug

Coffee/tea maker, fridge, microwave, oven

6. Deal Island Bay Cottage

Deal Island

Margaret H.

AED 1,028 total

includes taxes & fees

27 Aug - 28 Aug

7. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Point Lookout

William L.

AED 1,362 total

includes taxes & fees

17 Aug - 18 Aug

Smart TV, fireplace, table tennis, books

8. Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Point Lookout

Allie P.

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Top Smith Island Hotel Reviews

"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

8/10 Good

"Comfortable place, should have brought the boat. Worked out great with our 15 # dog"

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

10/10 Excellent

"Cottage was absolutely amazing. It provided a wonderful place to relax, swim and enjoy some quiet time as a family. They had everything you needed for the beach and the fire pit provided a wonderful view of the water. We had no issues and would recommend this place. Host was very accommodating and worked to make sure everything was great."

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

8/10 Good

"The Bay Estate is an absolute gorgeous property. However, host was not good at communicating and CLEANING CREWS NEED TO DO BETTER JOB!We had 11 mo old and 16 mo old babies with us; on day one, crawling and walking on the floors turned their knees/feet brown; the floors need a good mopping. The grill/sink and outdoor area was filthy, sent pictures to host, no remedy.The conservatory waterfall was not operating; asked if it could be turned on, no response. Plants in conservatory in desperate need of water and dead leaves need to be cleaned up. There is a steady drip in pipe in conservatory. Told host, no remedy.We couldn't locate a carafe for drip Cuisinart coffee maker. Host said they would check but we didn't hear back. When we arrived on Monday, 7/20, the 3 trash bins by the gate were full, when departing on Friday 7/24, the 3 bins were still full. We reached out to host asking what we were supposed to do with garbage, they stated garbage pickup is Friday and they would be back in touch on what we needed to do if they weren't empty Friday when we checked out. We did not hear from them so we left bags by bins. There were no kayaks on property as stated in information; if you are not going to provide kayaks, take them off your information.We replaced batteries in 2 of the tv remotes.THE BAY ESTATE IS A BEAUTIFUL PROPERTY (kitchen appliances are high quality, enormous kitchen table is a huge plus for large groups). Issues we had can be easily remedied."

Beautiful Bayfront with Sanctuary Private Beach

8/10 Good

"Place is nice and big. It’s in a quiet town which is what we were looking for. The place has well water but when you turn it on it smells like straight rotten eggs. It was definitely hard to shower because that’s all you can smell. During our stay we had some electrical issues but the owner was very attentive to it. Just wish it was caught before our stay. Overall we had a nice stay!"

Walkable Beach Retreat on Chesapeake Bay!

10/10 Excellent

"Such a great place to stay! Very equipped cottage. We rented a golf cart to get us around the island. Beach is walkable and the cottage has some chairs sand toys and umbrellas you can borrow. Caretaker Fran stopped by to make sure we had everything we needed too which was great. All the locals are super friendly and very welcoming. We will be back next summer for sure. Thank you"

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 Summer is here on Smith Island! Come out and enjoy a great season on the Bay 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 Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Tylerton County Dock and Horse Hammock are other places to visit while you're in town.

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.

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Check prices for these dates

Our top choices for Smith Island vacation rentals

1. Summer is here on Smith Island! Come out and enjoy a great season on the Bay

2. Cottage near the Bay

3. Tangier Escape, great place get away from it all on Deal Island, MD.

4. Newly updated 3 bedroom cottage with Solo Stove fire pit

5. Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom

6. Deal Island Bay Cottage

7. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

8. Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Find vacation rentals that suit your style

Top Smith Island Hotel Reviews

"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

Rodeway Inn at Somers Cove Marina

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Historic home on Smith Island w/ dock!

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Cottage near the Bay

Beautiful Bayfront with Sanctuary Private Beach

Walkable Beach Retreat on Chesapeake Bay!

Frequently asked questions

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