Family-friendly vacation rentals in Talbot County
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Top-rated family-friendly rentals in Talbot County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Talbot County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Annapolis
4.86 out of 5 average rating, 153 reviewsCharming Annapolis Water View Home
Oct 7 – 14
Home in Cambridge
5.0 out of 5 average rating, 9 reviewsSteps from Ironman MD Start
Jun 4 – 11
Home in St. Michaels
4.77 out of 5 average rating, 74 reviews*****Waterfront hs St. Michaels w/ private pool
Jan 11 – 18
Home in St. Michaels
Luxury Waterfront St. Michaels Home
Jan 15 – 22
Family- and pet-friendly home rentals
Home in Stevensville
4.84 out of 5 average rating, 86 reviewsChesapeake Bay Water Front Home w/ Private Pier
Feb 9 – 16
Home in Cambridge
4.87 out of 5 average rating, 89 reviewsAmazing views of The mighty Choptank
Jun 15 – 22
Home in Cambridge
5.0 out of 5 average rating, 5 reviewsPrime Ironman - cheer from lawn! Pet friendly!
Jan 22 – 29
Home in Saint Michaels
4.75 out of 5 average rating, 79 reviewsIn Town St. Michaels Waterview Cottage
Oct 24 – 31
Home in Saint Michaels
4.81 out of 5 average rating, 69 reviewsHarrison House - in Town and on St Michaels Harbor
Feb 28 – Mar 7
Home in Stevensville
5.0 out of 5 average rating, 14 reviewsStay & Play by the Bay - Sunsets- 4 KING Bedrooms
Dec 14 – 21
Home in Saint Michaels
4.89 out of 5 average rating, 80 reviewsCarpenter St. Cottage In Town St. Michaels!
Jan 20 – 27
Home in St Michaels
4.83 out of 5 average rating, 77 reviewsSt Michaels In Town Cottage with Location Location
Jul 12 – 19
Family-friendly home rentals with a pool
Home in Queenstown
4.83 out of 5 average rating, 30 reviewsEastern Shore Waterfront Retreat
Nov 19 – 26
Home in Sherwood
4.92 out of 5 average rating, 12 reviewsBeautiful, Private Retreat with HUGE Water Views!!
Dec 22 – 29
Home in East New Market
Beach haven family retreat
Jun 24 – Jul 1
Home in Cambridge
Turtle's Nest - Hist. Cambridge
Apr 2 – 9
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