Home Vacation Home Rentals By Owner In Orleans, MA

Showing 200 Of 255 Vacation Rentals
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Exceptional(2)

$834.31

/ Nightly
Private Vacation Home

Escape and Relax in this East Orleans home with magnificent in-ground heated pool

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

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(21)

$840.39

/ Nightly
Private Vacation Home

Family Home Close to Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(14)

$841.98

/ Nightly
Private Vacation Home

Private pool 3 mins to Skaket Beach!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(17)

$842.47

/ Nightly
Private Vacation Home

100 Ft to Skaket Beach!

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(7)

$849.8

/ Nightly
Private Vacation Home

Centrally located Orleans home w/ outdoor seatiing

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

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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$876.12

/ Nightly
Private Vacation Home

Crystal Lake Waterfront Cottage

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$876.12

/ Nightly
Private Vacation Home

Crystal Lake Waterfront Haven

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$888.62

/ Nightly
Private Vacation Home

Charming 6BR Orleans Retreat, Great Outdoor Space, Walk to Orleans Town

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(20)

$891.73

/ Nightly
Private Vacation Home

Arts and Crafts Style with Modern Amenities

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(18)

$894.24

/ Nightly
Private Vacation Home

Cape Cod Sunscape. Orleans

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

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(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(12)

$917.56

/ Nightly
Private Vacation Home

Comfortable, Cozy & Spacious Orleans Cottage on Quiet Road & Close to Everything

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 11

Sleeps
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Exceptional(11)

$934.14

/ Nightly
Private Vacation Home

close to town and Nauset beach, EV charger, air conditioning, outdoor shower.

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$954.42

/ Nightly
Private Vacation Home

Elegant Coastal Retreat with Ocean Views Near Mill Pond

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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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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$959.09

/ Nightly
Private Vacation Home

Spacious pet-friendly home, close to Nauset & Skaket beaches and Orleans village

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 9

Sleeps
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$961.42

/ Nightly
Private Vacation Home

Private Access to Nauset Beach, Beach Pass Included

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

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