Home Vacation Rentals By Owner In Orleans, MA

Showing 140 Of 283 Vacation Rentals
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Exceptional(6)

$298.54

/ Nightly
Private Vacation Home

Walk to Beach, Close to Town!

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(5)

$377.53

/ Nightly
Private Vacation Home

Coastal Comfort Near Orleans Adventures

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$451.42

/ Nightly
Private Vacation Home

1850 Orleans Antique Home with path to Arey’s Pond

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$291.36

/ Nightly
Cottage

Antique Cottage with King Bed, Kitchen, Bath, Private Yard & Path to Arey's Pond

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(23)

$485.27

/ Nightly
Private Vacation Home

Charming, Renovated 1870s Home with Private Beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(21)

$1896.76

/ Nightly
Private Vacation Home

Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(38)

$472.49

/ Nightly
Private Vacation Home

2nd floor Cottage, Oceanview, Deck, Shared Grill, & Outdoor Shower

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

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(10)

$574.25

/ Nightly
Private Vacation Home

Tranquil & sunlit home with peaceful yard, large deck, & fireplace - near beach

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 9

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(3)

$425.83

/ Nightly
Private Vacation Home

Stylish Orleans home with spacious deck - near bay & ocean beach

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(4)

$737.69

/ Nightly
Private Vacation Home

Cozy home close to the beach with deck, porch, W/D, & foosball table

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 5

Bath

Sleep 8

Sleeps
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Exceptional(2)

$443.27

/ Nightly
Private Vacation Home

Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore

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(14)

$825.15

/ Nightly
Private Vacation Home

Spacious home with huge deck & tree-lined yard, grill, & WiFi - great location

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(2)

$691.73

/ Nightly
Private Vacation Home

Quiet home near Pilgrim Lake with deck, W/D, AC, games, & large yard

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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$570.83

/ Nightly
Private Vacation Home

Elegant home with backyard pool & firepit - near beaches, shopping, & golf

Sandwich, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$539.06

/ Nightly
Private Vacation Home

Tonset Treasure with Bunk House

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(25)

$726.14

/ Nightly
Private Vacation Home

West-facing pure waterfront home in Orleans, overlooking Arey's Pond

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(21)

$604.75

/ Nightly
Private Vacation Home

Two-story home with new kitchen, washer/dryer, large yard, and pool table

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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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