House vacation rentals in Dorchester County
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Top-rated house rentals in Dorchester County
Guests agree: these houses 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 Dorchester County house rentals
House rentals with a pool
Home in Bivalve
5.0 out of 5 average rating, 6 reviewsFamily Retreat - Private Pool, 4 Bedroom, Fire Pit
Nov 9 – 16
Home in Cambridge
5.0 out of 5 average rating, 10 reviewsRELAX, You're on RIVER & POOL time!
Dec 18 – 25
Home in Lusby
4.91 out of 5 average rating, 67 reviewsSpacious and private waterfront, sleeps 10
Sep 19 – 26
Home in Cambridge
4.77 out of 5 average rating, 13 reviewsChesapeake Sunset Retreat
May 15 – 22
Home in Cambridge
4.97 out of 5 average rating, 90 reviewsChesapeake Sunset Cottage
Nov 15 – 22
Home in East New Market
4.92 out of 5 average rating, 26 reviewsLuxuryWaterfront Private Pool Dock Near Cambridge
Oct 29 – Nov 5
Home in Fishing Creek
4.9 out of 5 average rating, 10 reviewsBay Front Villa on Chesapeake
Jan 16 – 23
Home in Cambridge
4.96 out of 5 average rating, 99 reviewsWaterfront, Fabulous Home for Families with Pool!
Dec 5 – 12
Weekly house rentals
Home in Cambridge
4.89 out of 5 average rating, 28 reviewsLarge 3 BR in Historic Cambridge
Jan 23 – 30
Home in Fishing Creek
5.0 out of 5 average rating, 20 reviewsFishing Creek waterfront cottage
Apr 13 – 20
Home in Lusby
4.92 out of 5 average rating, 39 reviewsSoul Oasis - home on the Chesapeake Bay
Sep 4 – 11
Home in Cambridge
4.92 out of 5 average rating, 12 reviewsHigh St. Art Gallery Suite
Aug 17 – 24
Home in Cambridge
5.0 out of 5 average rating, 30 reviewsSmall, peaceful getaway
Mar 26 – Apr 2
Home in Cambridge
5.0 out of 5 average rating, 55 reviewsEntire Updated Waterview Home in Cambridge, MD
Jan 15 – 22
Home in Lusby
5.0 out of 5 average rating, 62 reviewsWaterfront with sweeping bay view & private beach
Dec 16 – 23
Home in Fishing Creek
5.0 out of 5 average rating, 10 reviewsSunrise Waterfront Cottage
Nov 11 – 18
Private house rentals
Home in Cambridge
4.96 out of 5 average rating, 26 reviewsWaterfrontQuietHotTubPvtPierFirePitKayakGrillCasa
Jul 15 – 22
Home in Deal Island Historic District
5.0 out of 5 average rating, 12 reviewsHouse of the Setting Sun/Deal Island Bayfront Home
Jan 29 – Feb 5
Home in Quantico
4.94 out of 5 average rating, 18 reviewsSunset Retreat on the Nanticoke
Sep 30 – Oct 7
Home in Cambridge
4.92 out of 5 average rating, 51 reviewsOsprey's Retreat - Waterfront with private beach!
Aug 7 – 12
Home in Cambridge
5.0 out of 5 average rating, 17 reviewsSchool Street Retreat: Cozy, artsy, central home
Jul 26 – Aug 2
Home in Lusby
4.94 out of 5 average rating, 62 reviewsLuxury bay house with sandy beach
Mar 18 – 25
Home in Madison
4.9 out of 5 average rating, 60 reviewsMagnificent Madison's private bay getaway home!!
Sep 2 – 9
Home in Oxford
5.0 out of 5 average rating, 38 reviewsStunning Chesapeake waterfront home
Oct 25 – Nov 1
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