Home Vacation Home Rentals By Owner In Orleans, MA

Showing 40 Of 255 Vacation Rentals
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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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$789.05

/ Nightly
Private Vacation Home

Inviting family escape with sunroom, deck, W/D & easy access to Nauset Beach

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(11)

$788.57

/ Nightly
Private Vacation Home

Beach & Golf Hub w/ All-Season Sunroom in Cape Cod

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(62)

$779.98

/ Nightly
Private Vacation Home

10-Minute Walk to Skaket Beach - Orleans - 5 Bikes - Close to Town - 2 AC Units

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(1)

$774.49

/ Nightly
Private Vacation Home

Capeside: 540-O Vintage Luxury in Orleans

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 4

Bath

Sleep 10

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(23)

$758.12

/ Nightly
Private Vacation Home

Peaceful Cape Cod retreat, 1.5mi to National Seashore

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$753.82

/ Nightly
Private Vacation Home

Home to Make Magical Summer Memories

East Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

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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$749.08

/ Nightly
Private Vacation Home

Classic Cape House 5M to Nauset Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

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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Exceptional(5)

$741.92

/ Nightly
Private Vacation Home

Adorable updated Cape in East Orleans!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(29)

$676.9

/ Nightly
Private Vacation Home

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$662.48

/ Nightly
Private Vacation Home

Waterfront Oasis with Game Space, Newly Renovated!

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(15)

$669.63

/ Nightly
Private Vacation Home

Beautifully remodeled cottage near the beach with central AC, gas grill & lawn

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$676.59

/ Nightly
Private Vacation Home

Beautiful Historic Home Within a Mile of Crystal Lake

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$678.52

/ Nightly
Private Vacation Home

4 Acre Private Estate on the Water

Orleans, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(1)

$683.73

/ Nightly
Private Vacation Home

Relaxing Cape Cod Hideaway with Modern Comforts

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(3)

$662.03

/ Nightly
Private Vacation Home

East Orleans Waterview Getaway

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(18)

$677.55

/ Nightly
Private Vacation Home

SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Orleans

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Exceptional(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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(18)

$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