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House vacation rentals in Dorchester County
Find and book unique houses on Airbnb
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
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Home in Lusby
4.91 out of 5 average rating, 69 reviewsSpacious and private waterfront, sleeps 10
![](https://a0.muscache.com/im/pictures/miso/Hosting-54391806/original/65a1eb21-367a-46ce-b2bd-63a15f9cef99.jpeg?im_w=720)
Home in Bivalve
5 out of 5 average rating, 8 reviewsFamily Retreat - Private Pool, 4 Bedroom, Fire Pit
![](https://a0.muscache.com/im/pictures/miso/Hosting-987115297418224632/original/82f74742-db10-4279-877f-ce2c477751d8.jpeg?im_w=720)
Home in Cambridge
5 out of 5 average rating, 16 reviewsRELAX, You're on RIVER & POOL time!
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Home in Cambridge
4.97 out of 5 average rating, 94 reviewsChesapeake Sunset Cottage
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Home in Woolford
4.98 out of 5 average rating, 55 reviewsGorgeous Waterfront-Beach, Pool, Pets- 7 Bd /5ba
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Home in Fishing Creek
4.94 out of 5 average rating, 18 reviewsBay Front Villa on Chesapeake
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Home in Lexington Park
4.93 out of 5 average rating, 67 reviewsSerenity Bay-Relaxing, Spacious House-Private Pool
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Home in East New Market
4.93 out of 5 average rating, 27 reviewsLuxuryWaterfront Private Pool Dock Near Cambridge
Weekly house rentals
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Home in Oxford
4.96 out of 5 average rating, 188 reviewsThe Oxford House
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Home in Lusby
4.94 out of 5 average rating, 160 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
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Home in Scotland
4.92 out of 5 average rating, 112 reviewsSpacious Gorgeous Waterfront Home with Sunset View
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Home in Cambridge
4.96 out of 5 average rating, 71 reviewsRoslyn Retreat. Center of the Eastern Shore!
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Home in Cambridge
4.94 out of 5 average rating, 18 reviewsHigh St. Art Gallery Suite
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Home in Fishing Creek
5 out of 5 average rating, 24 reviewsFishing Creek waterfront cottage
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Home in Fishing Creek
4.91 out of 5 average rating, 11 reviewsSunrise Cottage Hoopers Island. Fish, crab, relax!
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Home in Lusby
4.94 out of 5 average rating, 49 reviewsSoul Oasis - home on the Chesapeake Bay
Private house rentals
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Home in Oxford
5 out of 5 average rating, 40 reviewsStunning Chesapeake waterfront home
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Home in Cambridge
5 out of 5 average rating, 59 reviewsPeaceful Waterview Ranch Home in Cambridge, MD
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Home in Dameron
5 out of 5 average rating, 83 reviewsPeace Point - Waterfront, Secluded, Home w/hot tub
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Home in Cambridge
4.93 out of 5 average rating, 56 reviewsOsprey's Retreat - Waterfront with private beach!
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Home in Princess Anne
4.89 out of 5 average rating, 9 reviewsYe Ole Pirate House
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Home in Cambridge
4.92 out of 5 average rating, 76 reviewsWaterfront Oasis! Hot tub! 2+ acres - Sleeps 8
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Home in Deal Island Historic District
4.93 out of 5 average rating, 15 reviewsHouse of the Setting Sun/Deal Island Bayfront Home
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Home in Cambridge
4.97 out of 5 average rating, 37 reviewsSmall, peaceful getaway
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