Home Vacation Rentals By Owner In Orleans, MA

Showing 280 Of 283 Vacation Rentals
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Exceptional(26)

$480.13

/ Nightly
Private Vacation Home

Pet-Friendly Orleans Ranch (1560)

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(6)

Select Dates for Price
Private Vacation Home

Custom Cape Home Near Pleasant Bay & PahWah Pond (1580)

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(13)

$477.26

/ Nightly
Private Vacation Home

Nestled by Nauset

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

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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$316.37

/ Nightly
Cottage

Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away.

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(43)

$428.43

/ Nightly
Private Vacation Home

Central AC, Spacious, 5-level, beautiful home, near lakes and beach

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(6)

$728.21

/ Nightly
Private Vacation Home

Orleans Cape Cod, 3BR, Fire Pit, Central AC, 8 Min to Nauset Beach, Sleeps 10

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(28)

$1646.94

/ Nightly
Private Vacation Home

Enchanting Waterfront Summer Escape on Pleasant Bay

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 6

Sleeps
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Exceptional(36)

$804.39

/ Nightly
Private Vacation Home

Your perch to the Cape's best ocean view with private Nauset access for 8!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(33)

$803.28

/ Nightly
Private Vacation Home

Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(28)

$800.6

/ Nightly
Private Vacation Home

Five Bedrooms Plus a Fully Equipped Game Room! (2085)

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 18

Sleeps
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Exceptional(1)

$7021.28

/ Nightly
Private Vacation Home

Luxury 6 Bedroom Home

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(3)

$1626.14

/ Nightly
Private Vacation Home

Tonset Manor: 232-O East Orleans Vacation Estate Includes Guest House, Heated Pool, Hot Tub

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 12

Sleeps
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Exceptional(11)

$536.42

/ Nightly
Private Vacation Home

Close to Barley Neck Landing!

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

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(19)

$2322.82

/ Nightly
Private Vacation Home

The Meeting House: 023-O Private Orleans resort-style compound: heated pool/spa, fire pit & cabana

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(43)

$701.9

/ Nightly
Private Vacation Home

Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(26)

$2778.08

/ Nightly
Private Vacation Home

Private Estate, heated pool, outdoor kitchen, 9 bedrooms, 9.5 baths, sleeps 20

East Orleans, Massachusetts, United States

Bed 9

Bed

Bath 9

Bath

Sleep 21

Sleeps
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Exceptional(16)

$3567.11

/ Nightly
Private Vacation Home

Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24

Orleans, Massachusetts, United States

Bed 10

Bed

Bath 10

Bath

Sleep 24

Sleeps
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$1700.21

/ Nightly
Private Vacation Home

Oceanfront, Spectacular Views, Nauset Beach

Orleans, Massachusetts, United States

Bed 7

Bed

Bath 3

Bath

Sleep 16

Sleeps
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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

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