Home Vacation Rentals By Owner In Orleans, MA

Showing 180 Of 283 Vacation Rentals
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Exceptional(13)

$450.92

/ Nightly
Private Vacation Home

1.6 mi to Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(8)

$499.97

/ Nightly
Private Vacation Home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(29)

$392.57

/ Nightly
Private Vacation Home

Adorable home in the heart of East Orleans!

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(9)

$456.05

/ Nightly
Private Vacation Home

Private Lake Access, Great for Families!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(22)

$772.66

/ Nightly
Private Vacation Home

Steps to Nauset Beach, Private Yard!

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(10)

Select Dates for Price
Private Vacation Home

Renovated 3-Bedroom Cape with Private Backyard in Ideal Orleans Location

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Private Vacation Home

Private Retreat for Families Yet Near Everything in Orleans!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(5)

Select Dates for Price
Private Vacation Home

Nauset Heights - The Ocean At Your Doorstep! (2127)

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$753.09

/ Nightly
Private Vacation Home

Town Cove Coastal Chic

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(48)

Select Dates for Price
Private Vacation Home

Executive Waterfront Luxury Estate 6000 Sqft; Heated Pool; Elevator

East Orleans, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 16

Sleeps
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Exceptional(12)

$655.7

/ Nightly
Private Vacation Home

Spacious 5-Bedroom Retreat in the Heart of Orleans, MA

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$550.28

/ Nightly
Private Vacation Home

Game Room, Central AC, Dog Friendly!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(5)

$1692.33

/ Nightly
Private Vacation Home

Luxury home located 2 min walk from Skaket Beach. Sunny, spacious and private.

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$747.36

/ Nightly
Private Vacation Home

Sunny, Charming, Farmhouse - Kid Friendly

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$900.05

/ Nightly
Private Vacation Home

5-bedroom Cape with a pool and yard games.

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(5)

$758.56

/ Nightly
Apartment

Walk to Town, Fully Renovated!

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(11)

$1056.86

/ Nightly
Private Vacation Home

Pleasant Bay Beachfront Property Plus!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(18)

$364.72

/ Nightly
Apartment

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(1)

$453.51

/ Nightly
Private Vacation Home

Short Walk to Water, Mins to Nauset Beach, AC!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$805.34

/ Nightly
Private Vacation Home

Private Beach - 3 bedroom

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Orleans

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Exceptional(10)

$531.87

/ Nightly
Private vacation home

Experience the charm of Orleans at Skaket Beach Life

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$579.12

/ Nightly
Private vacation home

3 Mi to Nauset Beach! Family Home w/ Private Yard

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$578.17

/ Nightly
Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$573.31

/ Nightly
Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(10)

$571.12

/ Nightly
Private vacation home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(10)

$565.29

/ Nightly
Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$562.23

/ Nightly
Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(10)

$507.78

/ Nightly
Private vacation home

Rock Harbor Retreat: Perfect vacation home: Book Reservations for Summer 2027

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$499.97

/ Nightly
Private vacation home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$502.34

/ Nightly
Private vacation home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Most Popular Cities in Massachusetts