Smith Island Holiday Rentals

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Holiday Rentals in Smith Island

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!

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

10.0 out of 10, Exceptional, (14)
"The house is great, so clean and well-equipped and has everything you need for a comfortable stay. Kim delivered delicious crabs right to the dinner table! We enjoyed riding the bikes around the island. Smith Island Bakery is only a few doors down!"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

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

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is AU$370
includes taxes & fees
7 Jan - 8 Jan 2025
Deal Island Bay Cottage

Cottage near the Bay

8.8 out of 10, Excellent, (28)
"Our stay at the Cottage near the Bay was fantastic and exactly what my family needed. The host went above and beyond to communicate with us and make our stay excellent. The cottage was very clean, cozy, and a welcome escape. When we come back to Crisfield we won't be staying anywhere else, as long as it isn't already booked!"
The price is AU$322
includes taxes & fees
24 Dec - 25 Dec
Cottage near the Bay

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

9.8 out of 10, Exceptional, (31)
"very quiet, peaceful, relaxing location. The house had everything we needed. We would definitely stay there again."
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Virginia Retreat on Wicomico River w/ Dock!

10.0 out of 10, Exceptional, (16)
"My mom didn’t want to leave. Beautiful family retreat. Quiet and restful. "
Virginia Retreat on Wicomico River w/ Dock!

Waterfront Reedville Home w/ Private Dock!

10.0 out of 10, Exceptional, (14)
"Lovely home on large property. Easy walk to the dock. River area was beautiful. Large screened in porch was very nice. Sunrise on the river was amazing. Highly recommend!"
Waterfront Reedville Home w/ Private Dock!

Bay House with Amazing View & Swimming Pool (open May- Sept.)

9.8 out of 10, Exceptional, (116)
"It is a dream place; my family and I had a great time, thanks to Jenn's prompt response. It is a very comfortable place and well-equipped for whatever one needs. I'll try to look them up on Facebook to follow them. Thank you very much for everything; it is a beautiful place with amazing views "
Bay House with Amazing View & Swimming Pool (open May- Sept.)

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

9.6 out of 10, Exceptional, (49)
"We needed a last minute place to stay and Mary saved the day. The cleaning fee for a tiny place added on to the nightly fee was a bit high, but beggars can't be choosers!! "
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

When you want to get away from everything Magnolia shores 2 acres of tranquility

10.0 out of 10, Exceptional, (65)
"Great time with great hosts! "
When you want to get away from everything Magnolia shores 2 acres of tranquility

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (183)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Beautiful Bayfront with Sanctuary Private Beach

9.0 out of 10, Wonderful, (17)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach
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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Other types of properties in Smith Island you may be interested in

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!

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

10.0 out of 10, Exceptional, (14)
"The house is great, so clean and well-equipped and has everything you need for a comfortable stay. Kim delivered delicious crabs right to the dinner table! We enjoyed riding the bikes around the island. Smith Island Bakery is only a few doors down!"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

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.

Frequently asked questions

Can I find holiday rentals in Smith Island?

Yes, there are holiday rentals close to the most popular sights in Smith Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Smith Island has to offer?

Large waterfront cabin, kayaks & paddle boards, fire pit. Crabbing and fishing!: This holiday home rental outside of Smith Island is located on the waterfront, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Smith Island?

With 6 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Smith Point Marina and Point Lookout State Park.

What are holiday rentals like in Smith Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smith Island. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.