Dorchester Vacation Rentals - HolidayHomes base64Hash Dorchester Vacation Rentals - HolidayHomes

Dorchester Vacation Rentals

Browse 4,501 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Dorchester

Book the highest-rated Dorchester vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Apartment Dorchester
Super Location Boston 3 1/2, bd. Apt. Driveway Parking
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House Dorchester
Renovated Beach House Close to Everything, Minutes to Boston
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Apartment Dorchester
Child-friendly holiday apartment
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House Dorchester
Luxury Oceanfront Bayside Jewel
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Apartment Dorchester
Sunlit Spacious 3BR in Heart of Downtown Boston! Guest Favorite!
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Condo Dorchester
Condo with yard & terrace | Perfect for remote work
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Apartment Dorchester
Holiday apartment with yard & patio | City view
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Apartment Dorchester
Children-friendly apartment | Suitable for remote work
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Apartment Dorchester
Holiday apartment with yard
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Apartment Dorchester
SUNNY! BOOK NOW! FABULOUS! UbEr Cool Minutes to Center!
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House Dorchester
Child-friendly house | Near Freedom Trail | City view | Good for workation
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Condo Dorchester
Elegant Back Bay Brownstone-Comm Av 1 Bed - 1 Week Min, beyond 2 wks considered
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Apartment Dorchester
Beach Home next to Boston & T, King Bed, Park Free
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House Dorchester
Children-friendly house
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Apartment Dorchester
Fully equipped beautiful rental apartment | Pets allowed
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Top 15 most Recommended Vacation Rentals in Dorchester

Discover your ideal Dorchester vacation rental with real-time comparisons of 4,501 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Dorchester
Apartment ∙ 4 guests ∙ 3 bedrooms

130 m² Apartment

Dorchester, Boston, Massachusetts, United States
This family-friendly apartment rental for 4 is located at West Street and River Street and features a fully equipped kitchen.
from $93
per night
(2)
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Aparthotel Dorchester
2 guests ∙ 1 bedroom

Aparthotel

Dorchester, Boston, Massachusetts, United States
This cozy aparthotel in Bay Village accommodates 2 guests and features a refreshing outdoor pool for a relaxing stay.
from $58
per night
(140)
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House Dorchester
16 guests ∙ 8 bedrooms

House

Dorchester, Boston, Massachusetts, United States
This house rental in Dudley / Brunswick King accommodates 16 guests and features convenient parking for your stay.
from $506
per night
(9)
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Apartment Dorchester
Apartment ∙ 5 guests ∙ 2 bedrooms

74 m² Apartment

Dorchester, Boston, Massachusetts, United States
Spacious apartment rental for 5 in the Theatre District featuring a modern kitchen and easy access to local attractions.
from $158
per night
(10)
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Condo Dorchester
2 guests ∙ 1 bedroom

Condo

Dorchester, Boston, Massachusetts, United States
This cozy 2-bedroom condo in Prudential / St. Botolph features a heated pool for relaxation and enjoyment.
from $353
per night
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Apartment Dorchester
2 guests ∙ 1 bedroom

Apartment

Dorchester, Boston, Massachusetts, United States
This Theatre District apartment rental accommodates 2 and features a modern kitchen with stainless steel appliances.
from $145
per night
(16)
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Apartment Dorchester
Apartment ∙ 4 guests ∙ 2 bedrooms

28 m² Apartment

Dorchester, Boston, Massachusetts, United States
Spacious 4-person apartment rental in Upham's Corner featuring a modern kitchen and ample natural light throughout.
from $86
per night
(11)
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House Dorchester
10 guests ∙ 4 bedrooms

House

Dorchester, Boston, Massachusetts, United States
Spacious house rental in Highland Park for 10 guests featuring a beautiful yard perfect for outdoor gatherings.
from $231
per night
(26)
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Condo Dorchester
6 guests ∙ 3 bedrooms

Condo

Dorchester, Boston, Massachusetts, United States
This 6-person condo in Highland Park features a family-friendly atmosphere and a well-equipped kitchen for comfortable living.
from $287
per night
(2)
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