Title: Smith Island Vacation Home Rentals from CA $257: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Smith Island](https://expedia.ca/Smith-Island-Hotels.d553248634999169749.Travel-Guide-Hotels)[Vacation Rentals in Smith Island](https://expedia.ca/Smith-Island-Vacation-Rentals.d553248634999169749.Travel-Guide-VacationRentals)[Smith Island Car Rentals](https://expedia.ca/Car-Rentals-In-Smith-Island.d553248634999169749.Car-Rental-Guide)[Smith Island Vacation Packages](https://expedia.ca/Smith-Island.d553248634999169749.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Smith Island Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634999169749&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999169749&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999169749&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248634999169749&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Smith Island vacation homes ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/7fd7ada2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/59122c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/b3a6d12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/c86a14e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart [](https://www.expedia.ca/Smith-Island-Hotels-Get-Away-To-Relax-On-Smith-Island-In-The-Chesapeake-Bay.h92745551.Hotel-Information) Smith Island 9.8/10 Exceptional (15) "The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $310 CA $476 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Smith-Island-Hotels-Get-Away-To-Relax-On-Smith-Island-In-The-Chesapeake-Bay.h92745551.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/76000000/75700000/75693000/75692925/4c9a65a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75700000/75693000/75692925/c06dc96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75700000/75693000/75692925/0975380d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75700000/75693000/75692925/ab7d0ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage near the Bay [](https://www.expedia.ca/Crisfield-Hotels-Cottage-Near-The-Bay.h75692925.Hotel-Information) Crisfield 8.8/10 Excellent (52) "Srea was quiet, peaceful, plenty of information provided about the area restaurants, grocery stores, etc. Enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darla J M. CA $112 CA $257 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Crisfield-Hotels-Cottage-Near-The-Bay.h75692925.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w908h683x58y0-1d4078ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w905h683x60y0-4547a7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w906h683x59y0-6a81f3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w508h683x258y0-d2ed8821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly updated 3 bedroom cottage with Solo Stove fire pit [](https://www.expedia.ca/Reedville-Hotels-Bayberry-Newly-Updated-3-Bedroom-Cottage.h83500464.Hotel-Information) Reedville 9.8/10 Exceptional (18) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis A. CA $121 CA $327 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Reedville-Hotels-Bayberry-Newly-Updated-3-Bedroom-Cottage.h83500464.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71530000/71523200/71523122/w506h683x259y0-036dc1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71530000/71523200/71523122/w518h683x248y0-34c05dab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71530000/71523200/71523122/22058dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/72000000/71530000/71523200/71523122/w507h683x259y0-71128c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom [](https://www.expedia.ca/Reedville-Hotels-Reelin-Relaxin-Spacious-Farmhouse-In-Reedville.h71523122.Hotel-Information) Reedville 10/10 Exceptional (26) "We stayed while visiting for a family member graduation. The property was wonderful; the kitchen was well supplied and the little ones loved the games! Everything was very clean and comfortable. The owner was very responsive with any questions I had. We plan on staying here again the next time we are in town!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah B. CA $213 CA $510 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Reedville-Hotels-Reelin-Relaxin-Spacious-Farmhouse-In-Reedville.h71523122.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/118000000/117880000/117875200/117875165/88eb376c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117880000/117875200/117875165/54986971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117880000/117875200/117875165/adec908c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117880000/117875200/117875165/76df0f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tangier Escape, great place get away from it all on Deal Island, MD. [](https://www.expedia.ca/Deal-Island-Hotels-Tangier-Escape.h117875165.Hotel-Information) Deal Island Historic District CA $131 CA $283 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Deal-Island-Hotels-Tangier-Escape.h117875165.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117560000/117556700/117556661/e98146c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117560000/117556700/117556661/9252364a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117560000/117556700/117556661/2c49adea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117560000/117556700/117556661/15ac58a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly! [](https://www.expedia.ca/Reedville-Hotels-Bayfront-Oasis-With-Heated-Pool.h117556661.Hotel-Information) Reedville 8.0/10 Very good (1) "We had a great time. The host was very welcoming and helpful. Hope to go back again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) holly u. CA $689 CA $1,434 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Reedville-Hotels-Bayfront-Oasis-With-Heated-Pool.h117556661.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121350000/121341500/121341496/eaee0fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121350000/121341500/121341496/w1424h1068x1y0-7928d027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121350000/121341500/121341496/fcae67a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121350000/121341500/121341496/w1324h1343x0y0-d6263f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 4-Bedroom Waterfront Beachfront Home with Bay Views & Spa [](https://www.expedia.ca/Scotland-Hotels-4-Bedroom-Luxury-Private-Beach-Retreat.h121341496.Hotel-Information) Point Lookout 10/10 Exceptional (1) [](https://www.expedia.ca/Scotland-Hotels-4-Bedroom-Luxury-Private-Beach-Retreat.h121341496.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28®ionId=553248634999169749&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Smith+Island%2C+Maryland%2C+United+States+of+America®ionId=553248634999169749&latLong=37.981236%2C-76.029938&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Smith+Island%2C+Maryland%2C+United+States+of+America®ionId=553248634999169749&latLong=37.981236%2C-76.029938&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Smith+Island%2C+Maryland%2C+United+States+of+America®ionId=553248634999169749&latLong=37.981236%2C-76.029938&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Smith+Island%2C+Maryland%2C+United+States+of+America®ionId=553248634999169749&latLong=37.981236%2C-76.029938&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=VACATION_HOME) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSmith-Island-Private-Vacation-Homes.d553248634999169749-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSmith-Island-Private-Vacation-Homes.d553248634999169749-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Smith Island Hotel Reviews ![Home of the Terrapin King](https://images.trvl-media.com/lodging/117000000/116480000/116478300/116478280/55164d3b_y.jpg) ### Home of the Terrapin King 10/10 Excellent "It was an awesome weekend. My whole family made many memories and we can’t wait to come again! " [](https://expedia.ca/Crisfield-Hotels-Home-Of-The-Terrapin-King.h116478280.Hotel-Information) ![Rodeway Inn at Somers Cove Marina](https://images.trvl-media.com/lodging/30000000/29760000/29752800/29752751/f024af81_y.jpg) ### Rodeway Inn at Somers Cove Marina 10/10 Excellent "Room was very clean. Person at desk was very nice at check in time. " [](https://expedia.ca/Salisbury-Hotels-Rodeway-Inn.h29752751.Hotel-Information) ![Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views](https://images.trvl-media.com/lodging/101000000/100710000/100708800/100708738/5378f169_y.jpg) ### Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views 10/10 Excellent "Amazing house and property. Great for cooking and relaxing. We loved the pier!!" [](https://expedia.ca/Dameron-Hotels-Bay-Estate-By-AvantStay-Waterfront.h100708738.Hotel-Information) ![Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed](https://images.trvl-media.com/lodging/113000000/112880000/112877900/112877881/18697c32_y.jpg) ### Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed 10/10 Excellent "Wrote a lengthy review praising this property up and down & was cut off with a character limit. Just know this- this property is gorgeous and provides every single detail you could imagine. Beautifully decorated and maintained, all while the host goes above and beyond to stay in contact & provide the best experience possible. We had a 1/2 a week here for thanksgiving and created the most amazing memories in thanks to this host. We were able to join 2 families traveling from afar to cook, eat, enjoy family time inside and outside, so seamlessly because this home was so comfy & amazing. Comfy beds, amazing views, amazing kitchens, bathrooms, dining spaces, lounging spaces, TVs galore, games, ample space, fire pit, decks, grill huts, private beach, fresh oysters, lots of towels, new appliances and so much more- so many details provided throughout the homes. We talked about how we would absolutely return to this property. What a fabulous job you've done to give your guests a great experience. Our memories here are epic and this will always hold a special place in our hearts. Thank you!" [](https://expedia.ca/Reedville-Hotels-Private-5-Acre-Waterfront-Retreat-With-Main-Guest-House-Sleeps-12.h112877881.Hotel-Information) ![Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10](https://images.trvl-media.com/lodging/80000000/79740000/79735300/79735206/9a929552_y.jpg) ### Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10 10/10 Excellent "House was perfect for our needs! The extra kitchen cane in handy for Thanksgiving prep. The views were even more breathtaking than the pictures. Will absolutely look forward to renting again. Thank you! " [](https://expedia.ca/Heathsville-Hotels-Magical-Sunsets-And-Breathtaking-Views-In-HeathsvilleWicomico-River-Sleeps-10.h79735206.Hotel-Information) ![Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!](https://images.trvl-media.com/lodging/60000000/59830000/59829300/59829267/cb8d27bd_y.jpg) ### Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks! 10/10 Excellent "We greatly enjoyed our stay and exploring the area. The house is just like what in a retirement home with gameroom downstairs, a nice fire pit to enjoy at night by the water, and plenty of room. Next time we'd like to bring our grandkids to enjoy." [](https://expedia.ca/Reedville-Hotels-Blue-Crab-Hideaway-A-Waterfront-Retreat.h59829267.Hotel-Information) ![Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/7fd7ada2_y.jpg) ### Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart 10/10 Excellent "Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host." [](https://expedia.ca/Smith-Island-Hotels-Get-Away-To-Relax-On-Smith-Island-In-The-Chesapeake-Bay.h92745551.Hotel-Information) ![Private Beach Front Getaway at The Sunshine Beach Cottage.](https://images.trvl-media.com/lodging/69000000/68440000/68437600/68437545/632a8a21_y.jpg) ### Private Beach Front Getaway at The Sunshine Beach Cottage. 10/10 Excellent "Waking up to the rising sun on the Bay was spectacular. So peaceful and rejuvenating. Make sure you checkout out Calvert Cliffs State Park too. You’ll get a workout on the multiple trails and a beautiful shoreline at the end to find some natural treasures!! Sunshine Cottage was well equipped and clean as a whistle. Beds were amazingly comfortable too. Hosts Rhett and Kay couldn’t be more responsive to inquiries. Overall great experience and would recommend for a lovely getaway. Thank you!! Sallie " [](https://expedia.ca/Scotland-Hotels-Private-Beach-Front-Getaway-At-The-Sunshine-Beach-Cottage.h68437545.Hotel-Information) ![A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/1445eb3c_y.jpg) ### A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand 10/10 Excellent "the house was perfect! Jocelyn was a terrific host. She provided a welcome basket with cookies, materials for Smores. there are games, activities, beach toys, even bikes! The kitchen and entire house are well-appointed with absolutely everything you mighty need for a nice stay. Adorable interior decorating. Everything from bath towels to cookware are quite nice! The location is peaceful and quiet but you can hear the waves on the water from the open windows. Backyard had everything needed for family entertaining. We will definitely come back! Check in and check out were easy and flexible processes." [](https://expedia.ca/Scotland-Hotels-Enjoy-The-Hideaway-In-Hays-Beach-On-Chesapeake-Bay-With-Internet-301-250-8384.h22121103.Hotel-Information) ## Find out more about Smith Island ## Smith Island Vacation Homes information | Number of reviews | 110 | | ----------------- | ----------------- | | Accommodation | 77 Vacation Homes | | Lowest Price | CA $257 | | Highest Price | CA $510 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Janes Island State Park ](https://www.expedia.ca/4Star-Janes-Island-State-Park-Hotels.s40-0-d553248621532662318.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Kingston ](https://www.expedia.ca/4Star-Kingston-Hotels.s40-0-d553248635975867875.Travel-Guide-Filter-Hotels) - [B&B in Chance ](https://www.expedia.ca/Chance-Bed-And-Breakfast.d3000440451-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chance Hotels ](https://www.expedia.ca/Chance-Hotels.d3000440451.Travel-Guide-Hotels) - 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