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
Sep 14 – 21
Home in Lexington Park
4.94 out of 5 average rating, 65 reviewsSerenity Bay-Relaxing, Spacious House-Private Pool
Oct 11 – 18
Home in Cambridge
4.77 out of 5 average rating, 13 reviewsChesapeake Sunset Retreat
Dec 4 – 11
Home in Cambridge
4.97 out of 5 average rating, 90 reviewsChesapeake Sunset Cottage
Sep 30 – Oct 7
Home in Cambridge
5.0 out of 5 average rating, 7 reviewsRELAX, You're on RIVER & POOL time!
Jul 18 – 25
Home in Lusby
4.91 out of 5 average rating, 67 reviewsSpacious and private waterfront, sleeps 10
Dec 30 – Jan 6
Home in East New Market
4.92 out of 5 average rating, 26 reviewsLuxuryWaterfront Private Pool Dock Near Cambridge
Oct 25 – Nov 1
Home in Fishing Creek
4.9 out of 5 average rating, 10 reviewsBay Front Villa on Chesapeake
Apr 4 – 11
Weekly house rentals
Home in Scotland
4.92 out of 5 average rating, 107 reviewsSpacious Gorgeous Waterfront Home with Sunset View
Nov 4 – 11
Home in Cambridge
4.97 out of 5 average rating, 92 reviewsChurch Creek Charm (close to Blackwater Refuge)
Jul 4 – 11
Home in Cambridge
4.97 out of 5 average rating, 64 reviewsRoslyn Retreat. Center of the Eastern Shore!
Aug 28 – Sep 4
Home in Fishing Creek
4.9 out of 5 average rating, 10 reviewsSunrise Cottage Hoopers Island. Fish, crab, relax!
Nov 29 – Dec 6
Home in Lusby
4.92 out of 5 average rating, 37 reviewsSoul Oasis - home on the Chesapeake Bay
Dec 8 – 15
Home in Cambridge
4.89 out of 5 average rating, 27 reviewsLarge 3 BR in Historic Cambridge
Jan 19 – 26
Home in Fishing Creek
5.0 out of 5 average rating, 20 reviewsFishing Creek waterfront cottage
Nov 16 – 23
Home in Cambridge
4.89 out of 5 average rating, 9 reviewsHigh St. Art Gallery Suite
Dec 13 – 20
Private house rentals
Home in Lusby
5.0 out of 5 average rating, 62 reviewsWaterfront with sweeping bay view & private beach
Jan 9 – 16
Home in Cambridge
4.92 out of 5 average rating, 51 reviewsOsprey's Retreat - Waterfront with private beach!
Oct 9 – 14
Home in Deal Island Historic District
5.0 out of 5 average rating, 12 reviewsHouse of the Setting Sun/Deal Island Bayfront Home
Dec 11 – 18
Home in Quantico
4.94 out of 5 average rating, 18 reviewsSunset Retreat on the Nanticoke
Sep 16 – 23
Home in Deal Island Historic District
5.0 out of 5 average rating, 40 reviews"Promise Point" Bay front home with dock. 3BR 2BA
May 6 – 13
Home in Dameron
5.0 out of 5 average rating, 76 reviewsPeace Point - Waterfront, Secluded, Home w/hot tub
Mar 10 – 17
Home in Cambridge
4.96 out of 5 average rating, 26 reviewsWaterfrontQuietHotTubPvtPierFirePitKayakGrillCasa
Jul 24 – 31
Home in Westover
4.97 out of 5 average rating, 59 reviewsWaterfront Chesapeake Bay Retreat
Apr 14 – 21
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- Monthly Rentals Dorchester County
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