Home Vacation Rentals By Owner In Orleans, MA

Showing 20 Of 283 Vacation Rentals
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Exceptional(1)

$954.42

/ Nightly
Private Vacation Home

Spacious Skaket Beach Retreat

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(3)

$839.59

/ Nightly
Private Vacation Home

Bayside 2/10Mi to Skaket Beach

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(24)

$866.2

/ Nightly
Private Vacation Home

Peaceful Retreat Surrounded by Gardens and Water View

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(2)

$793.2

/ Nightly
Private Vacation Home

Newly Renovated Home

Truro, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(7)

Select Dates for Price
Private Vacation Home

Quiet Neighborhood .2 miles to Skaket Beach (1193)

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$1500.64

/ Nightly
Private Vacation Home

Waterfront Orleans Oasis with a Private Deep Water Dock

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath
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$479.87

/ Nightly
Cabin

On Bakers Pond, an Upscale Cabin

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(7)

$430.41

/ Nightly
Private Vacation Home

Dream Waterfront A-Frame in Orleans!

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$686.8

/ Nightly
Private Vacation Home

4BR Kenrick Woods Getaway

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(65)

$1234.92

/ Nightly
Private Vacation Home

5 bedrooms ocean view estate overlooking cape cod bay

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(17)

$443.42

/ Nightly
Private Vacation Home

Sleeps 8, Minutes to Nauset Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(8)

$426.77

/ Nightly
Private Vacation Home

Spacious Home with Sprawling Yard!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$1175.88

/ Nightly
Private Vacation Home

Artist Retreat Views of Ocean

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$1206.88

/ Nightly
Private Vacation Home

Cape Cod retreat near Nauset Beach with pool oasis

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(35)

$1252.77

/ Nightly
Private Vacation Home

Spacious home w/Heated Pool - Perfect for multiple families

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(58)

$333.06

/ Nightly
Private Vacation Home

Quaint Cape Near Beaches And Centrally Located

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(51)

$542.98

/ Nightly
Private Vacation Home

Celebrate July4th week 2026 at the Cranberry Cottage!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(96)

$349.36

/ Nightly
Private Vacation Home

East Orleans - walk to Nauset Beach

East Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$720.05

/ Nightly
Private Vacation Home

Family Fun: Huge Game Room, Outdoor Shower & Walk 2 Lake – 10 min to Ocean & Bay

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(21)

Select Dates for Price
Private Vacation Home

Tranquil Orleans Escape on Namequoit River with Views (1091)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Home Most popular vacation rentals in Orleans

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Exceptional(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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(21)

$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