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Smith Island Cottage Rentals & Holiday Homes
Find the best cottages in Smith Island - We found 8 exact matches
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About Smith Island Luxury Rental on Hawaii Wedding Travel
Searching for cottages to rent near Smith Island? Hawaii Wedding Travel features more than 8 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Smith Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Hawaii Wedding Travel’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Smith Island.
Are you planning to travel to the lakeside, beach, or mountain area? Hawaii Wedding Travel’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Hawaii Wedding Travel boasts of 8 holiday cottages and places to stay in Smith Island. The site provides unique Airbnb, VRBO, Hawaii Wedding Travel-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Smith Island Cottage Rentals
What are the top rated Cottage Rentals in Smith Island?
There are a lot of options in Smith Island. If you plan on staying in the Smith Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Smith Island:
- Chesapeake Waterfront with Private Dock in Crisfield, Maryland
- Come, sit back and relax at the "Catch of the Bay"
- Home of the Terrapin King
- Walk to Main Street: Family-Friendly Crisfield Gem
- Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
- Walk to Main St Condo with Pool Access in Crisfield
- Walkable Beach Retreat on Chesapeake Bay!
- Tangier Escape, great place get away from it all on Deal Island, MD.
- Cute, cozy cottage getaway
- Come escape to Smith Island for the winter and enjoy nature, peace and quiet
How much does it cost to rent a cottage in Smith Island?
The average cost for a cottage rental in Smith Island is $203 per night. Hawaiiweddingtravel has a wide list of great cottages near Smith Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Smith Island that allow pets?
Yes, here are the top cottage rentals in Smith Island that allow you to bring your pet:
- IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
- Unique Tangier Cottage with Chesapeake Bay Views!
- Unique Tangier Cottage w/Chesapeake Bay Views!
- Pet-Friendly Smith Island Cottage with Golf Cart!
- Come, sit back and relax at the "Catch of the Bay"
- Walk to Main St Condo with Pool Access in Crisfield
- Rodeway Inn at Somers Cove Marina
- Walk to Main Street: Family-Friendly Crisfield Gem
See all pet-friendly vacation rentals in Smith Island on Hawaiiweddingtravel
Do you have any rental cottages in Smith Island that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Smith Island to find one that works for you.
Are there quality cottages in Smith Island that have indoor swimming pools?
As of 2026, the data from Hawaiiweddingtravel shows that there are Over 8 private swimming pools or cottages with indoor pools in the Smith Island area along with other great amenities.