Holiday rentals in Smith Island

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Top-rated holiday rentals in Smith Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.
2–9 OctIndividual Host,
£73 per night
4.98 out of 5 average rating, 292 reviews
Guest favourite
Home in Reedville
Sunkissed Cottage-private, natural waterfront home
Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.
6–13 AugIndividual Host,
£143 per night
4.97 out of 5 average rating, 116 reviews
Guest favourite
Farm stay in Onancock
Private romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!
20–27 AugIndividual Host,
£155 per night
4.99 out of 5 average rating, 166 reviews

Popular amenities for Smith Island holiday rentals

Other great holiday rentals in Smith Island

Guest favourite
Cottage in Reedville
Bull Neck Cottage
31 Aug – 7 SeptIndividual Host,
£123 per night
4.95 out of 5 average rating, 114 reviews
Guest favourite
Cottage in Onancock
Waterfront romantic getaway Eastern Shore w dock
7–14 JanIndividual Host,
£161 per night
4.97 out of 5 average rating, 191 reviews
Guest favourite
Flat in Lexington Park
Private apartment with kitchenette
16–23 OctIndividual Host,
£64 per night
4.93 out of 5 average rating, 187 reviews
Guest favourite
Tiny home in Cambridge
Blackwater Refuge House on The Farm, water access
28 Jun – 5 JulIndividual Host,
£95 per night
4.99 out of 5 average rating, 153 reviews
Guest favourite
Tiny home in Accomac
Little Red House on a Farm - Quiet Rural Waterview
29 Dec – 5 JanIndividual Host,
£113 per night
4.93 out of 5 average rating, 436 reviews
Guest favourite
Cabin in Deltaville
"The Little Red Cabin" aka The Galley
6–13 DecProfessional Host,
£96 per night
4.98 out of 5 average rating, 251 reviews
Guest favourite
Guest house in Saluda
Wooded Cabin retreat on fresh water pond
6–13 SeptIndividual Host,
£85 per night
4.93 out of 5 average rating, 463 reviews
Guest favourite
Cottage in Heathsville
HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
4–11 JulIndividual Host,
£135 per night
4.94 out of 5 average rating, 175 reviews
Guest favourite
Cottage in Westover
Heaven on the Bay - A Peaceful Waterfront Retreat
24 Sept – 1 OctIndividual Host,
£225 per night
4.92 out of 5 average rating, 139 reviews
Guest favourite
Flat in Belle Haven
Salty Dog Compound
20–27 JanIndividual Host,
£126 per night
4.92 out of 5 average rating, 139 reviews
Guest favourite
Loft in Lusby
Coastal Treetop Retreat
8–15 JulIndividual Host,
£118 per night
5.0 out of 5 average rating, 303 reviews
Guest favourite
Cottage in Smith Island
IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK
10–17 JunIndividual Host,
£161 per night
5.0 out of 5 average rating, 37 reviews

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