Home Vacation Rentals By Owner In Orleans, MA

Showing 220 Of 283 Vacation Rentals
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Exceptional(7)

$652.37

/ Nightly
Private Vacation Home

Walk to Rock Harbor Beach from your spacious Orleans coastal retreat

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(2)

$484.13

/ Nightly
Cottage

Charming 2-bedroom cottage in wonderful Barley Neck area of Orleans with WiFi AC

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(14)

$783

/ Nightly
Cottage

Peaceful Nauset Beach Sanctuary

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(11)

$1078.61

/ Nightly
Private Vacation Home

2 Min Walk to Private Beach & Boat Launch!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(12)

$2912.92

/ Nightly
Private Vacation Home

New Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(16)

$406.76

/ Nightly
Private Vacation Home

Walk to Beach, Home with Central A/C. Private Acre+ Lot

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(90)

Select Dates for Price
Private Vacation Home

Highly Rated Cottage in Orleans, Cape Cod

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(5)

$377.8

/ Nightly
Private Vacation Home

5 Min Walk to Swimmable Mill Pond, Dog Friendly!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Cottage

Quaint cottage in Orleans, 2 bedrooms, upper deck, 2 miles to Nauset beach.

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$657.87

/ Nightly
Cottage

The Parson’s Cottage

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$314.42

/ Nightly
Private Vacation Home

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(9)

$1790.74

/ Nightly
Private Vacation Home

Piece of Paradise: 054-OL Magnificent Orleans Estate w/Pool, Tennis, Assoc. Beach on Pleasant Bay

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(15)

$426.83

/ Nightly
Private Vacation Home

1 Mile to Nauset Beach! Family and Dog Friendly!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(57)

$1115.51

/ Nightly
Private Vacation Home

5 Min Walk to Nauset Beach, Heated Pool & Hot Tub

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(15)

$1812.51

/ Nightly
Private Vacation Home

Fabulous Family CapeHouse, with Views, Beach & Dock! Gatherings Inside and Out!

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(13)

$1895.3

/ Nightly
Private Vacation Home

Large House w/ample space- steps from Skaket Beach, close to CCRT and downtown!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(13)

$909.76

/ Nightly
Private Vacation Home

Pochet Association - Nauset Beach Access - Central Air (2161)

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(37)

$995.02

/ Nightly
Private Vacation Home

Luxurious Waterfront Home!

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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$320.9

/ Nightly
Private Vacation Home

Beautiful Waterfront Property on Lonnie`s Pond in East Orleans

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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$458.39

/ Nightly
Private Vacation Home

Chic Boho Escape Minutes to Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Orleans

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$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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$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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$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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$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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$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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$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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$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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$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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$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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$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