0+ Beds for 1+ Guests
Price  $10 - $1000+

Dorchester Vacation Rentals and Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Dorchester vacation homes and short term rentals from 2 rental sites including TripAdvisor, FlipKey and more, ranging from $41 to $1,362 a night. 
Showing 133 personalized results
    $350 / night
    The Farm House in Dames Quarter, Maryland
    The Farm House in Dames Quarter, Maryland
    6 bed / 7 bath
    Nanticoke Acres, MD
    $350 / night
    The Farm House in Dames Quarter, Maryland
    The Farm House in Dames Quarter, Maryland
    6 bed / 7 bath
    Nanticoke Acres, MD
    $225 / night
    Villa Wenona - Waterview Villa  by Chesapeake Bay
    Villa Wenona - Waterview Villa by Chesapeake Bay
    4 bed / 3 bath
    Wenona, MD
    $190 / night
    "The Cottage" Cambridge Chesapeake Waterfront Home
    "The Cottage" Cambridge Chesapeake Waterfront Home
    3 bed / 1 bath
    Dailsville, MD
    $1100 / night
    Yr Round Estate on Bay / Family Reunions Sleeps 28
    Yr Round Estate on Bay / Family Reunions Sleeps 28
    7 bed / 6 bath
    Seawilde, MD
    $150 / night
    Eastern Shore getaway
    Eastern Shore getaway
    3 bed / 3 bath
    Salisbury, MD
    $500 / night
    Chesapeake Bay Waterfront, Private Dock, Beach
    Chesapeake Bay Waterfront, Private Dock, Beach
    6 bed / 3 bath
    Dailsville, MD
    $900 / night
    Maryland Eastern Shore Waterfront Estate
    Maryland Eastern Shore Waterfront Estate
    8 bed / 6 bath
    Hampton, MD
    $900 / night
    Maryland Eastern Shore Waterfront Estate
    Maryland Eastern Shore Waterfront Estate
    8 bed / 6 bath
    Hampton, MD
    $135 / night
    Eastern Shore's Finest Bed and Breakfast
    Eastern Shore's Finest Bed and Breakfast
    1 bed / 1 bath
    Nanticoke Acres, MD
    $250 / night
    Tilghman Landing
    Tilghman Landing
    1 bed / 2 bath
    Lodgecliff, MD
    $710 / night
    CEDAR POINT
    CEDAR POINT
    3 bed / 2 bath
    Brad Vern Park, MD
    $710 / night
    CEDAR POINT
    CEDAR POINT
    3 bed / 2 bath
    Brad Vern Park, MD
    $250 / night
    Water water everywhere in this gorgeous home
    Water water everywhere in this gorgeous home
    3 bed / 2 bath
    Wenona, MD
    $250 / night
    Water water everywhere in this gorgeous home
    Water water everywhere in this gorgeous home
    3 bed / 2 bath
    Wenona, MD
    $125 / night
    Hoopers Island Studio,  360 Degrees WATER VIEWS
    Hoopers Island Studio, 360 Degrees WATER VIEWS
    1 bed / 1 bath
    Swan Harbor, MD
    $125 / night
    Hoopers Island Studio,  360 Degrees WATER VIEWS
    Hoopers Island Studio, 360 Degrees WATER VIEWS
    1 bed / 1 bath
    Swan Harbor, MD

    Information about Dorchester

    Vacation Rentals In Dorchester

    Looking for a vacation rental in Dorchester? Tripping.com has 6 rental homes available in Dorchester. Potential renters will find 0 studios, 3 1-bedroom, 1 2-bedroom and 2 rentals with 3 or more bedrooms ranging from $41 a night to $1,362 a night. Many of these properties are instantly bookable.

    The average price of a nightly rental in Dorchester is $487 while the average price of a weekly rental is $4,968. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Dorchester home is $1,212.

    Search properties from 5 rental sites in Dorchester where the top providers in that area are HomeAway, VRBO, and FlipKey. There are 62 HomeAway rentals, 49 VRBO short term rentals and 11 FlipKey vacation rentals.

    Wondering if you can bring your favorite dog or cat with you? We have 2 pet friendly vacation rentals available for you. In addition to accommodating pets, Dorchester rentals offer a variety of amenities. In particular, 4 rentals have internet and wifi, 5 have TV and/or cable and 5 have a pool or hot tub.