Home Vacation Rentals By Owner In Orleans, MA

Showing 260 Of 283 Vacation Rentals
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Exceptional(57)

$530.59

/ Nightly
Private Vacation Home

AVAILABLE WEEK OF AUGUST 23! Renovated private & spacious Orleans 3B-2B.

Orleans, Massachusetts, United States

Bed 3

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(5)

$702.46

/ Nightly
Private Vacation Home

5BR Luxe Coastal Vibes: Room to Spread out. Wine Bar, Hot Tub, Bikes, Game Room

Orleans, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(13)

$379.71

/ Nightly
Private Vacation Home

Walk to Skaket Beach or Bike to Rail Trail!

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(32)

$999.89

/ Nightly
Private Vacation Home

Private Beach Access, Large House in the Woods

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(30)

$291.52

/ Nightly
Private Vacation Home

A comfortable house in a quiet neighborhood, but close to EVERYTHING Cape Cod.

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$585.8

/ Nightly
Private Vacation Home

Private Pool Near Pleasant Bay Beach

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$1293.14

/ Nightly
Private Vacation Home

Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the store

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(11)

Select Dates for Price
Condo

Walk to the beach at Little Pleasant Bay from this newly decorated cottage!

Orleans, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(38)

$521.89

/ Nightly
Private Vacation Home

Charming Family-Friendly Home On Beach Rd. Close To Nauset Beach & Village Ctr.

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(48)

$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(15)

Select Dates for Price
Private Vacation Home

Expansive Home by Orleans Town Landing (1086)

Orleans, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(17)

$506.08

/ Nightly
Private Vacation Home

Cozy Home in Quiet & Convenient Area (1140)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(13)

$599.31

/ Nightly
Private Vacation Home

Private Retreat on Pilgrim Lake! (1507)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(16)

Select Dates for Price
Cottage

Pets Welcome Near Town & Bike Trail (1471)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(4)

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Private Vacation Home

Beautifully Decorated 3BR Cape - Less than .5 miles to Beach! (1945)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(13)

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Private Vacation Home

Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215)

Orleans, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

Select Dates for Price
Condo

Refurbished Cottage with Views of Town Cove (1038)

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(9)

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Private Vacation Home

Quaint Cottage Close to Skaket Beach (1912)

Orleans, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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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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Home Most popular vacation rentals in Orleans

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Exceptional(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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(26)

$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