
Smith Island vacation rentals
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Top-rated vacation rentals in Smith Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Smith Island
Top guest favorite

Home in Kilmarnock
5 out of 5 average rating, 58 reviewsSecluded beach front cottage on the Chesapeake Bay
AngieRating, 5 stars6 days ago
My absolute favorite airbnb ever ! This was the 3rd time I've stayed here, and if I could afford it, I'd go monthly. The location is perfect, right on the water, small private beach, lots of privacy and soooo incredibly relaxing. The house is very well laid out, super clean and comfortable. Keri provides more than most hosts, from the kitchen and bathrooms, to beach gear, movies, books, games, and the kayaks ! I love love love this house and location so very much. It feels like "my" home away from home and I'll continue to go back as much as possible. THANK YOU again Keri, for another amazing getaway !
Guest favorite

Tiny home in Nanticoke
4.86 out of 5 average rating, 57 reviewsLa Cabaña
DelaneyRating, 5 stars2 months ago
This was an amazing stay! It was so cozy and comfortable which was great as it rained most of our stay. The kitchen was great to cook in, with all the utensils and spices you may need. Definitely a great spot for rest and relaxation!
Top guest favorite

Cabin in Westover
5 out of 5 average rating, 44 reviewsChalet Style Home, private country setting
AprilRating, 5 stars2 months ago
I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.
Top guest favorite

Guesthouse in Heathsville
5 out of 5 average rating, 34 reviewsSerene Country Cottage
SarahRating, 5 stars1 week ago
I thought the place itself was even nicer than the photos showed. It was quaint, clean, and cozy! The hosts were very helpful with their instructions. Perfect little peaceful getaway. Especially if you love animals.
Guest favorite

Home in Lusby
4.92 out of 5 average rating, 79 reviewsSpacious and private waterfront, sleeps 10
MichaelRating, 5 stars4 weeks ago
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.
Top guest favorite

Home in Salisbury
4.98 out of 5 average rating, 196 reviewsBeautiful Renovated Home, Perfect Getaway!
DanielleRating, 5 stars1 week ago
This was our second time staying at this rental and we would recommend to others. Ann's communication was great and she even gave us the option to check in early and check out late as it was available.
Superhost

Home in Lusby
4.89 out of 5 average rating, 37 reviewsWaterfront home with three bedrooms,3 full baths
JoyceRating, 5 stars1 week ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Guest favorite

Home in Port Republic
4.75 out of 5 average rating, 20 reviewsFamily Friendly: Hot Tub, Grill, Pool & More!
JosueRating, 5 stars1 week ago
Me and some friends stayed here and we all loved it. More than enough space and so much stuff/activities from movie nights to playing pool to hitting the hot tub and more to do in the house! We would definitely stay here again and the host was great.
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- Assateague Island National Seashore
- Gerry Boyle Park
- Cape Charles Beachfront
- Wallops Beach
- Bow Beach
- Ragged Point Beach
- Langford Sand
- Guard Shore
- Snead Beach
- Parramore Beach
- Saint Jerome Beach
- Lane Beach
- Oxford Beach
- Tankards Beach
- Haven Beach
- Wilkins Beach
- Gargathy Beach
- Cedar Island Beach
- Assateague Beach
- Sandyland Beach
- Cordreys Beach
- St George Island Beach
- Piney Point Beach
- Great Egging Beach