Vacation rentals with a kayak in Southern Maryland
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Southern Maryland
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southern Maryland kayak rentals
House rentals with a kayak
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
Dec 24 – 31
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Feb 18 – 25
Home in Cambridge
4.99 out of 5 average rating, 142 reviewsSunset Breezes - quiet waterfront retreat
Nov 21 – 28
Home in Lusby
5.0 out of 5 average rating, 135 reviewsCove Point Beach Home 1 &1/2 blocks to Beach
Dec 27 – Jan 3
Home in Lexington Park
4.97 out of 5 average rating, 139 reviewsPrivate beach retreat in historic St. Mary's City
Sep 21 – 28
Home in Lusby
4.99 out of 5 average rating, 175 reviewsCove Point Cottage with Chesapeake Bay views
Oct 16 – 23
Home in Shady Side
5.0 out of 5 average rating, 117 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Mar 27 – Apr 3
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
Nov 11 – 18
Cottage rentals with a kayak
Cottage in Kinsale
4.95 out of 5 average rating, 195 reviewsGreat little cottage with a "Rivah" view
Apr 13 – 20
Cottage in Smith Island
4.97 out of 5 average rating, 184 reviewsLevering Creek Cottage with Private Docking
Feb 10 – 17
Cottage in Saint Michaels
4.99 out of 5 average rating, 137 reviewsLa Casita on Harris Creek, St. Michaels
Jun 4 – 11
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Dec 19 – 26
Cottage in Reedville
4.9 out of 5 average rating, 161 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Nov 2 – 9
Cottage in Edgewater
4.99 out of 5 average rating, 129 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Dec 20 – 27
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Oct 4 – 11
Cottage in Onancock
4.96 out of 5 average rating, 138 reviewsA "True" Chesapeake Bay Waterfront Experience!
Jul 15 – 22
Cabin rentals with a kayak
Cabin in Lusby
4.91 out of 5 average rating, 209 reviewsPeaceful Waterfront Retreat on The Bay
Sep 16 – 23
Cabin in Lusby
4.94 out of 5 average rating, 144 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Jul 17 – 24
Cabin in Reedville
4.97 out of 5 average rating, 188 reviewsDinna Fash-3 BR Waterfront Log Cabin
Jul 21 – 28
Cabin in Lusby
4.98 out of 5 average rating, 59 reviewsYour own private beach? Horizon views of the bay?
Sep 25 – Oct 2
Cabin in Lusby
4.98 out of 5 average rating, 44 reviewsLakeside Cabin with Arcade & Firepit
Oct 5 – 12
Cabin in Ridge
4.97 out of 5 average rating, 31 reviewsPizza Friday
Jan 2 – 9
Cabin in Reedville
4.94 out of 5 average rating, 71 reviewsCoastal Cabin - hot tub, private beach & kayaks
Feb 16 – 23
Cabin in Reedville
4.67 out of 5 average rating, 12 reviews"Elderberries" Chesapeake Bayfront Cottage
Jun 16 – 23
Destinations to explore
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